connecticut towns to visit in fall

11 Of The Most Beautiful Fall Destinations In Connecticut

Elisa Regulski

Elisa is a passionate travel writer with over five years of experience. After graduating with a B.F.A in acting from Oklahoma City University, Elisa earned a M.A in mass communication From Texas State University. When she's not writing about all of the amazing places throughout the U.S., she can be heard singing with her band.

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The best places to visit in Connecticut in the fall are calling you! So throw on your cozy jacket and lace up your hiking shoes! It’s time to experience the best fall getaways in Connecticut. We all know The Nutmeg State is home to enchanting autumn views, but these 11 places really make the season sparkle.

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What do you think are the best places to visit in Connecticut in the fall? Share your thoughts with us in the comments below!

Looking for more places to go leaf-peeping? Take this 2-hour fall foliage drive through Connecticut .

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Best activities in connecticut in the fall.

What are some great fall hikes in Connecticut?

There are some amazing fall hikes in Connecticut . New England is known for stunning fall foliage, and one of the best ways to enjoy it is on an autumn hike. The Lover’s Leap Trail in New Milford is a short but sweet hike perfect for a fall afternoon. The .4-mile hike crosses a stunning red iron bridge, which is a gorgeous contrast to the natural, colorful fall foliage. The Chauncey Peak Trail in Meriden is another great fall hiking option. This 2.2-mile trail overlooks a lake surrounded by picturesque trees with orange, red, and yellow foliage.

What are some fall day trips to take in Connecticut?

For a memorable fall day in Connecticut , hop aboard the Essex Steam Train and Riverboat. The historic train takes you through the Connecticut River Valley, where you can enjoy fall foliage in the marshland and along the river. Afterwards, board the Becky Thatcher Riverboat for some awesome fall scenery. It’s the perfect way to spend the day with friends or family and take in the amazing Connecticut views.

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Explore Connecticut

Fairfield Southwest

Hartford Central

Litchfield Northwest

Mystic Eastern

New Haven South Central

Fall foliage in connecticut 2024, historic town festivals, farm visits & colorful vistas.

Connecticut shows its brightest colors in early October. Best places to visit are the wooded areas of the state, like the Northwest Hills , the hilly Eastern parts of the state north of the Mystic, CT area , and upscale Fairfield County which is an quick drive or train ride from New York City. All these places have delightful small towns and gorgeous scenic drives. The fall colors are just part of the natural charm of Connecticut. The capital city of Hartford, CT has a beautiful city park, Bushnell Park , while New Haven, CT hosts the larger and more rugged East Rock Park . And around the state you'll find vineyards along the Connecticut Wine Trail that host harvest season events and tastings in fall.

Essential Information :

• Foliage Map (State of CT DEP)
• Pick Your Own Farms - Stop off for fresh apples, veggies, cider, pumpkins, baked goods and more!
• Connecticut State Map
• Great Things To Do in Connecticut - foliage train trips, harvest sales, seasonal events and scenic drives.

Foliage Driving Routes in Connecticut

Litchfield county & northwest ct :, new milford, kent, and mount tom state park -- 46 miles.

This drive will take travelers past the Housatonic River, famous for fly fishing and white water rafting; near two covered bridges; and through Kent, CT and its many art galleries, historic homes and churches; Washington, CT and its Institute for Native American Studies, and Mount Tom State Park . The Appalachian Trail passes through this area, and opportunities for day hikes are plentiful.

Points of Interest :

• Two covered bridges in the area are Bull's Bridge in Kent, CT and Kent Falls Bridge in Kent Falls State Park. Bull’s Bridge is a historic bridge, built in 1842; the Kent Falls bridge is a 1970s-era re-creation of a historic structure.
• Iron Mountain Preserve in Kent, CT : Stop for a 1.5-mile walk on a loop trail through varied forest and woodlands. Your host is the Nature Conservancy.
• The House of Books , also in Kent, CT , is packed with high-quality literature; a whole rooms of children's books; cards, music and gifts. The town is on the Appalachian Trail and the store specializes in maps, trail guides, books on local lore and the out-of-doors.

Side Trips :

• Travel a few miles north on Route 7 beyond Calhoun Corners , through Housatonic Meadows State Park , and into Cornwall, CT to see the West Cornwall covered bridge, which carries Route 128 across the Housatonic River. This area is famous for its great fall foliage, too.
• Mount Tom State Park in Litchfield, CT : Swimming and boating in the lake, hiking to a fire tower 1,325 feet above sea level.
• Institute for American Indian Studies in Washington, CT : Visit this museum to learn about the area’s first human residents. See the sachem’s house classroom, children’s discovery room, replicated Algonquian village, simulated archaeological excavation site.
• Kent Coffee and Chocolate Co. in Kent, CT : The cure for low energy, before or after a glorious hike in the Litchfield countryside. Come enjoy and take home gourmet chocolates and handmade desserts and truffles. Lots of interesting coffees, teas, and smoothies.
• Hopkins Vineyard in Warren, CT : Located just north of Lake Waramaug, this farm has been in operation and owned by the same family for well over 200 years. Tastings, tours and events are regularly available.
• Eateries in New Milford, CT show great range: The Iron Rail , featuring a range from artisan dishes and casual fare; and the Three Brothers Family Restaurant , with a Greek diner-style menu and reports that the slice of carrot cake they give you is as big as your head!

Torrington to Norfolk Through People's State Forest -- 58 miles

• People's State Forest & American Legion State Forest in Barkhamsted, CT : These two adjacent state forests are located along the west branch of the Farmington River. There are lots of places for picnicking. Check out the forests’ trail map and take a walk.
• Lake McDonough Park in Barkhamsted, CT : Stop for a picnic or a foliage hike on a scenic trail.
• Warner Theater in Torrington, CT : Leaf-peaking is a daytime activity, obviously, but if you are staying in the Litchfield Hills on a long weekend, check out what’s going on at this historic theater.
• Infinity Music Hall in Norfolk, CT : Echoing the comment above, if your trip through the beautiful towns and farms of Litchfield keeps you overnight, the Infinity Music Hall is a dynamic place that brings in lots of interesting, national-caliber entertainment.
• Thorncrest Farm & Milk House Chocolates in Goshen, CT is on the state’s Chocolate Trail. Calling itself The Home of Single Cow Origin Chocolates , Thorncrest serves chocolate in all the divine ways we have come to know and love.
• Jerram Winery in New Hartford, CT is on the Connecticut Wine Trail - wineries and vineyards that open their doors to tours, tastings, and sometimes classes and celebrations.

Waterbury Area Loop -- 42 miles

Nearby points of interest :.

• Brass Mill Center in Waterbury, CT : Home to great shopping, dining, activities and entertainment.
• The Palace Theater in Waterbury, CT : A historic theater presenting concerts, musicals, stage plays and other live shows.
• Southford Falls State Park in Oxford, CT : Hiking along the river and falls here during foliage season is quite wonderful.

Mystic County & Eastern CT :

Last green valley scenic byway -- 35 miles.

• Connecticut Audubon’s Grassland Bird Conservation Center at 218 Day Road in Pomfret Center, CT . Walk from dawn to dark, year-round, at the Bafflin Sanctuary or the Trail Wood Sanctuary . It’s all about the birds.
• Brooklyn, CT and the Brooklyn Green Historic District . This classic Connecticut town green is a beauty. Most buildings in the district date from 1750 to 1850.
• Taylor Brook Winery on Route 171 in Woodstock, CT welcomes guests Fridays through Sundays for tastings, self-guided vineyard tours, picnicking on the property, and a chance to buy cheese, sausage, crackers, dips, and other treats to enjoy with your wine.
• Driving west out of Brooklyn, CT on Route 6 takes you to the James. L. Goodwin State Forest in Hampton, CT , where you can take a walk on the many trails around Pine Acres Lake or visit a native plant wildlife garden.
• Alpaca Obsession in the town of Moosup, CT raises alpacas and angora rabbits and sells related products. Be sure to call ahead before visiting.

Dining and Shopping :

• Woodstock, CT is stocked with shopping that you won’t find in a big-box store. Pop in at Garden Gate Florist and Gift Shop (antiques, jewelry, plants) or Scranton's Shops (antiques in a historic blacksmith shop).
• Sweet Peas Fine Foods & Farm Market on Providence Road in Brooklyn, CT serves upscale take-out food, prepared meals, salad bar, quick cuisine, Venda Ravioli products, bakery goods, cheese. Perfect for a healthy and delicious picnic.
• The Stomping Ground on Main Street in Putnam, CT is a friendly local hangout with good lunches and dinner, live music nightly except Mondays and Tuesdays, and open mic nights.

Mystic and Old Mystic Via River Road -- 6 miles

• Mystic Seaport in Mystic, CT . Marvelous living history museum and re-creates a 1830-period New England ship building village similar to historic towns of this area. Lots of season special events celebrating coastal New England history and culture. Great fun for adults and kids.
• Mystic Aquarium and Institute for Exploration , also in Mystic, CT : Wonderful aquarium includes Beluga whale exhibit and Titanic exhibit developed with help by Dr. Robert Ballard, discoverer of the sunken ship.

Norwich-Woodstock Turnpike -- 32 miles

• Creamery Brook Bison in Brooklyn, CT : How often can you meet a bison? Farm welcomes visitors for special seasonal events and fun. Great for kids and families.
• Connecticut Audubon Society Center in Pomfret, CT : Spend some time outdoors with Audubon -- it wants you to meet the wilderness.

North Stonington to Sterling on Route 49 -- 22 miles

• Pachaug State Forest , Voluntown (860-376-4075). The Pachaug State Forest offers trails for hikers, snowmobilers, and horseback riders.

New Haven & South Central CT

Essex to guilford ct shoreline loop drive -- 35 miles.

• Essex Steam Train and Riverboat in Essex, CT : Enjoy a lazy ride up the lower Connecticut River in the lavish, antique railroad cars, then shift to a Mississippi-style river boat to complete your journey on the water.
• Hammonasset Beach State Park in Madison, CT . Connecticut's largest shoreline park with lots of smooth beach for swimming and sunning, along with a fun boardwalk.
• Bishop's Orchards in Guilford, CT . Fun place to get out of the car, stretch, buy apples and pumpkins and autumn treats. Great for kids and families.
• On the way from Essex, CT to Old Saybrook, CT , you can take a short side trip eastward on Route 95 across the Connecticut River to Old Lyme, CT and visit the Florence Griswold Museum . This marvelous house operated in the early 1900s as a boarding house for a summer colony of New York artists, and it’s a hot spot for American Impressionism. You will see lots of art and beautiful gardens.
• When you reach Hammonasset Beach State Park, swing northward on Route 450 for a stop in nearby Madison, CT . There you will find a great bookstore, R.J. Julia Booksellers . Excellent book selection, gifts, kids activities, and special events.
• Penny Lane Pub in Old Saybrook, CT : an English style pub and restaurant with a friendly, neighborhood atmosphere. Located on the state’s Signature Cocktail Trail.
• Bufalina in Guilford : Enjoy authentic Neapolitan pizza from a wood fired brick oven. Located on the state’s Pizza Trail.
• Chamard Vineyards in Clinton, CT : Try a glass of their wine at their French-inspired bistro that serves lunch and dinner. Live music is presented on Friday through Saturday in the tasting room. Located on the state’s Wine Trail.
• The Wharf Restaurant at Madison Beach Hotel in Madison, CT : Serving fresh and locally sourced foods that spotlight the flavors of the Atlantic Northeast and New England. Eat in the dining room or on the year-round porch.

Shoreline and Country Roads Drive Route -- 57 miles

• About 4.5 miles east of Branford, CT on Route 146, you might enjoy at small side trip to see shoreline where ferries depart for the Thimble Island Cruises . Simply take a right turn at Taken for Granite Antiquities on Leetes Island Road (which crosses Route 146) and head south on Thimble Island Road toward the village of Stony Creek, CT . After a breath of sea air or an island cruise, return to Route 146 via Thimble Island Road.
• The Guilford, CT green is a nice place to see a classic Connecticut town center. And the Guilford Art Center on Church Street may have something arty going on for your entertainment.
• Durham, CT is the northern terminus of the loop, and from here, the directions below take you back southward. For a short trip for pick-your-own apples, sunflowers, baked goods, and a great farm stand, head a little north out of Durham along routes 17 to 147 to Lyman Orchards in Middlefield, CT .
• The shoreline is not the best place to see foliage, but if you love ocean beaches, you might want to swing over for a stop at Hammonnassett Beach State Park in Madison, CT . Truly one of the state’s finest oceanside parks, with walk and a nature center.

Greater Hartford & Central CT :

Talcott mountain state park and heublein tower -- 7 miles.

• Talcott Mountain State Park , 57 Gun Mill Road, Bloomfield (860-242-1158)
• Penwood State Park , 57 Gun Mill Road, Bloomfield (860-242-1158)
• Heublein Tower , Summit Ridge Drive, Bloomfield (860-242-1158). Gilbert Heublein was a German hotelier and restaurateur in Hartford and a developer of gourmet food. He built the Tower in 1914 as a summer vacation home for his family. The tower is open only in summer, but the property is accessible year-round for hiking and wildlife viewing.

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5 Favorite Fall Connecticut Towns to Visit

Mystic | Connecticut

Fall in Connecticut…

September is just around the corner and now is a great time to start planning your New England day trips and weekend escapes . Today, I am sharing my five favorite fall Connecticut towns & regions to visit in this most cherished and charming New England season. As a Connecticut resident, we have spent our weekends here exploring our state in all the seasons. Here are some stand-out places to visit in The Nutmeg State this fall.

Mystic Country

Mystic, Connecticut is a beautiful place to visit in the fall. From cider donuts to a foliage cruise on the river, here are my favorite fall stops in this coastal region.

Stay: The Whaler’s Inn

Do: B.F. Clydes Cider Mill for apple slushies and cider donuts, Whittle’s Willow Spring Farm for pumpkin picking and their autumnal market, Mystic River Cruises for a fall foliage river cruise in an antique boat

Eat: Sift Bakery , Via Emilia , Shipwright’s Daughter , S&P Oyster , Red 36

Farmington Valley

The Farmington River Valley with its bucolic roads and historic towns is a fall must in my opinion. One of my favorite places in October.

Stay: The Farmington Inn

Do: Visit Hillstead Museum and walk the grounds, get your fall harvest at The Pickin’ Patch in nearby Avon, visit the petting zoo at Flemig Farm , head over to Simsbury for wine and produce at Rosedale Farms .

Eat: Millwright’s Restaurant & Tavern , Piccolo Arancio

Old Wethersfield & Glastonbury

Old Wethersfield is our hometown and it is really special in the fall. From Scarecrows Along Main to Webb-Deane-Stevens Museum’s Witches and Tombstones Tours, it’s a fun one to add for a day trip. Neighboring Glastonbury is full of orchards, farms, and farm stands too.

Stay: Silas W. Robbins Inn

Do: Shop the harvest and get a pumpkin latte at Heirloom Market , Graveyard Ghost Tours with The Webb Museum, pick up pumpkins and apple fritters at The Old Cider Mill , go apple-picking at Belltown Hill Orchards and shop their great market.

Eat: Heirloom Market , The Charles , Lucky Lou’s Bar & Grill , Saluyita , Ken’s Corner , Two Hopewell Bistro & Tavern

Litchfield Hills

A drive through Connecticut’s Litchfield Hills is a fall must when the colors arrive. Quaint towns abound and there are some great stops along the way as you meander these country roads. Kent, Washington, Litchfield and Cornwall are personal favorites for leaf-peeping.

Stay: Mayflower Inn & Spa

Do: Hogan’s Cider Mill for hard cider and fall harvest, hike Kent Falls State Park , apple picking at Averill Farm , ice cream and cheeses from Arethusa Farm Dairy , drive to Cornwall for leaf-peeping and to see the Cornwall Covered Bridge , Thorncrest Farm for chocolates.

Eat: Mayflower Inn , Arethusa Al Tavolo , GW Tavern

*Just to note: I’ll be updating my Litchfield Hills guide with a visit and stay this October. More soon!

Historic Essex

Essex, Connecticut is a personal favorite and in the fall it’s one of the prettiest Main Streets in my opinion. Love the shopping here too.

Stay: The Griswold Inn

Do: Shop Main Street, indulge in chocolates and cookies at Truffle Shots , take a fall foliage ride aboard the Essex Steam Train & Riverboat , tour Gillette Castle & State Park

Eat: Fireside dining at The Griswold Inn , Savour Cafe , Grano Arso , Noah’s 36

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These are some of my personal fall favorites in Connecticut. I’ll be sharing more of these places this year with guides for each region/town.

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The 7 Best Places to See Fall Colors in Connecticut

As fall sweeps into the Northeast, the entire region transforms into a swath of red, yellow, and orange, but each state has particular places that offer the most stunning views of the autumn colors. In Connecticut, the best places to see the foliage are in state parks and forests, which also offer viewing towers and lookouts so that you'll be able to treat yourself to a panoramic view of nature's vibrant display. 

Colors start to appear in late September and they can last through early November, but the peak time around Connecticut tends to be mid-October. The exact timeframe depends on the weather and other variables, but the Department of Energy and Environmental Protection keeps a handy weekly update so you can know exactly when to go.

If you want to check out other fall colors throughout the state, you can also take a scenic  driving tour  of the foliage.

Talcott Mountain State Park

 Matt Simmons / Getty Images 

Heublein Tower is a 165-foot tower located within  Talcott Mountain State Park  in Simsbury, Connecticut. When you visit in the fall, the top of the tower offers sweeping views that take in the Farmington River Valley and, on a clear day, several neighboring states. To get there, take Route 18 toward Simsbury. Once inside the park, park along the road near the trailhead of the hike. Hike the 1.25-mile trail to the ridge and bear left to get to Heublein Tower.

Until September 30, the tower is open Thursdays through Mondays. From October 1 through October 29, it's open Wednesdays through Mondays (closed on Tuesdays) and the opening hours are 10 a.m. to 5 p.m.

Mohawk State Forest

Kenneth Casper / Flickr / CC BY 2.0 

Make the Lookout Tower in Mohawk State Forest a stop on your fall foliage route. From the top, scenic views to the north and west include the Catskill, Taconic, and Berkshire mountain ranges. Hikers can pick the Mattatuck or Mohawk Trails, which cross the site. You can also see ample wildlife here, such as deer, fox, and bobcats.

From Torrington, drive west on Route 4 for 14 miles to the park entrance, Toumey Road, on the left. At the "T" intersection, turn right onto Mohawk Mountain Road. The lookout tower is at the end. 

Haystack Mountain State Park

VisionsofAmerica / Joe Sohm / Getty Images

At  Haystack Mountain State Park , you can drive a windy mountain road and hike a rugged trail to reach the top of Haystack Mountain, where you'll be rewarded with 360-degree, stunning views of the Berkshires, New York, and the Green Mountains. The road only goes about halfway up, so to get to the 34-foot lookout tower at the summit, you'll have to hike the rest of the way up from the road's end, which is about a half-mile. 

To get there from Norfolk, Connecticut, at the junction of Route 44 and Route 272, take the latter north half of a mile to the park entrance on the left. The entry road leads to the parking area.

Peoples State Forest

Chris Connelly / Flickr / CC BY 2.0

The  Peoples State Forest offers a few lookouts to see stunning colors. In particular, take the Jessie Gerard Trail (1.3 miles), which offers two paths to the Chaugham Lookouts. At the fork, the right path leads you through the lighthouse sight to the lookouts. The left path is a more direct route to the overlooks by way of 299 steps. Either way will lead you to the overlook that offers some of the best views in the state. 

At the junction of Route 318 and Route 181 in Pleasant Valley, Connecticut, travel east over the bridge and take the first left onto East River Road. The Jessie Gerard Trailhead is 2.4 miles ahead on the right. The yellow-blazed trail leads to two lookouts. 

Pachaug State Forest

Morrow Long / Wikimedia Commons / CC BY 2.0

Pachaug State Forest , established in 1928, is the largest one in Connecticut, comprising 26,477 acres spread across six towns. When you get to the forest, there are two main areas you can explore—the Champman Area and the Green Falls Area. For foliage, your best bet is to explore the first, as the Chapman Area is where the Mount Misery overlook is located, which is the highest point in the area at 441 feet. You can reach the overlook by car or by trail. 

The forest entrance is on Route 49, about a half-mile north of Voluntown. Turn left into the entrance and drive two miles west, bearing left at the fork to the parking lot. The woods access road on the left leads to the overlook. 

Macedonia Brook State Park

Susan Popielaski / Wikimedia Commons / CC BY-SA 3.0

Make your way to  Macedonia Brook State Park , in Kent, Connecticut, to view a splash of fall colors from the top of Cobble Mountain. From this vantage point, you'll be able to view the Harlem Valley into the Taconic and the Catskill Mountains.

From the intersection of Route 341 and Route 7 in Kent, take Route 341 heading west, and then stay left at the intersection of Macedonia Brook and Fuller Mountain roads. From the parking lot, head to the Cobble Mountain Trail. 

If you spend a day exploring the area, there are several other parks nearby, including Mohawk State Forest, Kent Falls State Park, Lake Waramaug State Park, and Housatonic Meadows State Park. 

Shenipsit State Forest

Morrowlong / Wikimedia Commons / CC BY-SA 3.0

Shenipsit State Forest offers you a chance to view beautiful fall foliage. Take the Shenipsit Trail, which will lead you to the top of Soapstone Mountain where the observation tower is located. The Civilian Conservation Corps Museum is also located within the park, but it's only open in the summer and closes after Labor Day.

To get there from Somers, take Route 190 east for a little over a mile to a blinking yellow traffic light. Turn right on Gulf Road and drive about 2 miles to Soapstone Mountain Road (the first right after Mountain View Road). The road leads to the tower parking lot, and the Shenipsit Trail runs by the tower. 

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Best Places to Visit in Connecticut in the Fall

Connecticut, known for its charming towns, scenic landscapes, and rich history, transforms into a mesmerizing wonderland during the fall season. As the leaves change colors, the state offers a plethora of experiences for travelers seeking the quintessential New England autumn. Best Places to Visit in Connecticut in the Fall, Join us as we explore the best places to visit in Connecticut in the fall and uncover the beauty of this enchanting season.

Explore Connecticut Outdoors

Immerse Yourself in Nature’s Palette

WHERE TO GO IN CONNECTICUT FOR A DAY TRIP?, Connecticut’s natural beauty shines brightest in the fall. Best Places to Visit in Connecticut in the Fall, Here’s how to make the most of the great outdoors:

Hiking Trails:

Connecticut boasts numerous hiking trails that take you through a blaze of autumn colors. Best Places to Visit in Connecticut in the Fall, Explore sections of the Appalachian Trail or take a leisurely stroll in state parks like Sleeping Giant and Talcott Mountain.

Land of the Free, Home of the Brave: Discover the spirit of liberty in the USA!”

Scenic Drives:

Hit the road on scenic routes like Route 169 or the Merritt Parkway. Best Places to Visit in Connecticut in the Fall, You’ll be treated to breathtaking vistas of red, orange, and gold leaves against the backdrop of historic villages.

Leaf Peeping:

Visit Litchfield Hills, the Quiet Corner, or the Farmington Valley for some of the best leaf-peeping spots. Best Places to Visit in Connecticut in the Fall, The foliage typically reaches its peak in early to mid-October.

Stars, Stripes, and endless possibilities. Welcome to the heart of the USA!”

Savor Some Fall Favorites

Taste the Flavors of Autumn

FUN PLACES TO GO IN CT THAT ARE OPEN, Connecticut’s fall is not just a treat for the eyes but also for the taste buds:

Pumpkin Everything:

Fall wouldn’t be complete without pumpkin-flavored treats. Enjoy pumpkin pies, lattes, and even pumpkin beer at local breweries.

Enjoy pumpkin pies, lattes, and even pumpkin beer at local breweries.

Farmers’ Markets:

Explore farmers’ markets for fresh produce, artisanal cheeses, and homemade goodies. Best Places to Visit in Connecticut in the Fall, These markets showcase the best of Connecticut’s culinary scene.

Seafood Feasts:

Fall is a great time to savor Connecticut’s seafood. Try clam chowder, lobster rolls, and fresh oysters at seaside restaurants.

FUN THINGS TO DO IN CT FOR YOUNG ADULTS,  Connecticut’s natural beauty shines brightest in the fall. Best Places to Visit in Connecticut in the Fall, The crisp air and rustling leaves create the perfect setting for an outdoor adventure.

Hit the road on scenic routes like Route 169 or the Merritt Parkway. Best Places to Visit in Connecticut in the Fall, You’ll be treated to breathtaking vistas of red, orange, and gold leaves against the backdrop of historic villages. These drives are a photographer’s dream, capturing the essence of fall in every frame.

Apple Picking:

Head to one of Connecticut’s orchards for a quintessential fall activity. Pick crisp apples, sip warm cider, and savor apple cider donuts. Best Places to Visit in Connecticut in the Fall, It’s not just about the apples; it’s about creating cherished memories with friends and family.

Savor apple cider donuts. It’s not just about the apples; it’s about creating cherished memories with friends and family.

Savor Some Fall Favorites:

Connecticut’s fall is not just a treat for the eyes but also for the taste buds.

Fall wouldn’t be complete without pumpkin-flavored treats. Best Places to Visit in Connecticut in the Fall, Enjoy pumpkin pies, lattes, and even pumpkin beer at local breweries. The aroma of cinnamon and nutmeg fills the air, making every bite a delight.

Fall is a great time to savor Connecticut’s seafood. Best Places to Visit in Connecticut in the Fall, Try clam chowder, lobster rolls, and fresh oysters at seaside restaurants. The cool coastal breeze adds to the charm of dining by the water.

What is the Best Time to See Fall Colors in Connecticut?

Timing is key.

The peak of fall foliage in Connecticut typically occurs in early to mid-October. However, the timing can vary depending on the region and weather conditions. To catch the vibrant colors, plan your visit accordingly.

Where to Stay in Connecticut?

Cozy Retreats

Connecticut offers a range of accommodations to enhance your fall getaway:

Charming Inns:

Stay in historic inns nestled in picturesque towns like Mystic, Essex, or Litchfield. Best Places to Visit in Connecticut in the Fall, These inns provide a cozy and intimate atmosphere.

Rustic Cabins:

Embrace the outdoors with a stay in a rustic cabin in state parks or near hiking trails. It’s a perfect way to connect with nature.

Luxury Resorts:

Pamper yourself in luxury resorts and spas. Enjoy breathtaking views, fine dining, and rejuvenating spa treatments.

Fall’s Majesty in Connecticut

Connecticut’s fall season is a time of unparalleled beauty and culinary delights. Best Places to Visit in Connecticut in the Fall, Whether you’re hiking through vibrant forests, sipping warm cider, or exploring charming villages, the Nutmeg State offers an autumn experience like no other. So, plan your trip, pack your sweaters, and immerse yourself in the enchanting fall magic of Connecticut. Create memories that will warm your heart long after the leaves have fallen. Fall in Connecticut is not just a season; it’s a celebration of nature’s grandeur and the simple joys of life.

People Also Ask :

Is connecticut pretty in the fall.

Yes, Connecticut is known for its beautiful fall foliage, making it a picturesque destination in the autumn months.

What months are fall in CT?

Fall in Connecticut typically spans from September to November, with peak foliage occurring in October.

Where can I see fall foliage in New Haven CT?

In New Haven, you can see fall foliage in places like East Rock Park, West Rock Ridge State Park, Sleeping Giant State Park, and along scenic drives in the surrounding countryside.

What are the cities in CT?

Some of the cities in Connecticut include Hartford, New Haven, Bridgeport, Stamford, Waterbury, Norwalk, Danbury, and New Britain, among others.

Plan your trip with ontravelx and get ready for a journey full of breathtaking sights and priceless memories.

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10 Best Things to Do in Connecticut in the Fall

By Author Meg Frost

Posted on Last updated: October 22, 2023

Categories United States of America (USA)

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Looking to visit Connecticut in the Fall this year? I grew up there and still visit countless times each year, so I’ve got all the scoop on the best things to do.

Keep reading for the best ways to see Fall foliage in Connecticut, the best haunted houses and hayrides, fun apple orchards, and more. 

Check out the Hollowed Harvest display

A family-friendly Halloween activity in Connecticut is the Hollowed Harvest lights display.

Hollowed Harvest uses jack-o-lanterns to create spooky (but kid-friendly) scenes, like dinosaurs and aliens. 

It’s a bit like a walk-through Christmas lights display, but Halloween themed!

TIP : Hollowed Harvest events are also available in Massachusetts, New York, and Virginia.

Hollowed Harvest @ Camp Mattatuck 221 Mt. Tobe Rd Plymouth, CT

Watch the Spooky Popcorn film series

If you’re a fan of scary movies, check out Hartford’s Spooky Popcorn event. 

On select nights in October, a scary movie is screened at Hartford’s Constitution Plaza. 

A sampling of movies include Stephen King’s Misery , Pan’s Labyrinth , and Coraline .

Check out the Spooky Popcorn webpage linked below for dates, times, and complete movie listing.

Spooky Popcorn @ Constitution Plaza 1 Constitution Plaza Hartford

Go on a hot air balloon ride

A unique way to experience Fall foliage in Connecticut is on a hot air balloon ride with Berkshire Balloons.

Berkshire Balloons runs their early morning flights from 5 different locations across Connecticut, including Bethlehem, New Hartford, and Southington.

Advanced reservations are recommended and can be made by calling (860) 620-3754.

Challenge yourself at The Adventure Park

Another unique way to immerse yourself in the gorgeous Fall colors in Connecticut is to spend a day at The Adventure Park in Storrs.

The Adventure Park includes several adventure courses of varying difficulty. 

The courses include rope climbing, ziplining, and bridges, all built up in the trees.

Another activity available at The Adventure Park is axe throwing, which can be reserved for parties as well.

The Adventure Park at Storrs, CT 2007 Storrs Rd Storrs

Go apple picking at Bishop’s Orchards

Located in Guilford, Bishop’s Orchards offers a ton of Fall activities for family fun or an adults-only outing.

First up is their pick-your-own offerings. Depending on when you visit in the Fall, you can pick your own apples, peaches, pears, raspberries, and pumpkins.

In addition, the on-site farm market offers pre-made meals, apple cider, fruit, veggies, baked goods, cheese, edible cookie dough, and other goodies. There’s also an ice cream stand next to the market.

Last, but not least, Bishop’s Orchards also has a winery where you can do wine and hard cider tastings, as well winery tours on the weekend.

Bishop’s Orchards 1355 Boston Post Rd Guilford

Get lost in the wine maze at Holmberg Winery

If you like wine and adore Fall, head to Holmberg Winery in Gales Ferry. 

Holmberg Winery hosts a wine maze on select dates in August and September. 

The premise is that in order to do a wine tasting, you must find each tasting set up in several locations throughout a corn maze. How fun!

If you’re more interested in the wine or hard cider tasting without the maze, their wine barn is open Friday-Sun through the end of October.

Visit their website below for more information, including dates for the wine maze

Holmberg Winery 1990 CT-12 Gales Ferry

Do a rail bike tour

Another fun way to see Fall foliage in Connecticut is via rail bike. 

Never heard of a rail bike? Neither had I until recently! 

In a nutshell, a rail bike is like a paddleboat, except instead of being in water, you’re on railroad tracks.

The Essex Steam Train & Riverboat runs 2 rail bike tours, one over moderate terrain and one over more difficult terrain.

The tours take 1.5-2 hours and are priced per bike with 2 and 4-person bikes available.

Visit their website linked below for more information, including dates and prices.

Rail bikes @ Essex Steam Train & Riverboat 1 Railroad Ave Essex

Check out the fall foliage at Talcott Mountain State Park

If you haven’t visited Talcott Mountain State Park in Simsbury during the fall season, then you’re missing out.

Seriously, it’s like nature decided to have a party and invited all the autumn colors to show up. The park’s foliage is so breathtaking, you’ll feel like you’re walking through a painting.

And if that’s not enough to convince you, let’s talk about the Heublein Tower at the top of the mountain.

Yeah, you can hike up there any old time, but during fall, the view is extra spectacular. You’ll want to snap some pictures for Instagram, trust me.

So grab your hiking boots and let’s get to Talcott Mountain State Park before the season ends. You won’t regret it.

Talcott Mountain State Park 1 Summit Ridge Dr. Simsbury

Get spooked on a ghost tour

What better way to get into the Halloween spirit than a ghost tour?

There are 2 companies that run ghost tours that I recommend.

First up is Ghosts of New Haven , which takes guests on a ghost tour of New Haven, home of Yale University. 

Ghosts of New Haven also arranges private ghost pub crawls in New Haven, as well.

Another fun tour company offering ghost tours in Connecticut is Seaside Shadows Tours in Mystic.

Seaside Shadows offers several haunted tours including a downtown Mystic ghost tour, 2 separate graveyard tours, and 2 separate ghost tours aboard boats. 

They also host a paranormal investigation on Halloween weekend at a local cemetery.

Explore Gillette Castle State Park

Ah, the crisp autumn air, the sound of leaves crunching underfoot, and the majesty of Gillette Castle State Park in East Haddam.

If you want to truly immerse yourself in the beauty of this historic spot, there’s no better time than Fall.

The colors of the trees lining the Connecticut River are breathtaking (and super Instagram-worthy).

Plus, the cooler temperatures mean you can comfortably explore the castle without working up a sweat.

Gillette Castle State Park 67 River Rd East Haddam

Try not to get scared at Legends of Fear

Legends of Fear is not for the faint of heart – and really only for preteens and older!

This spooky experience, located in Shelton, features 2 haunted experiences, a haunted hayride and a haunted trail (which also includes access to haunted houses!). 

Guests can pick 1 or both experiences, depending on how much scaring they can take in 1 night!

Please visit their website linked below for exact dates and ticket pricing.

Legends of Fear 2 Saw Mill City Rd Shelton

Ride Rails to the Darkside

Head to the Connecticut Trolley in Museum in East Windsor for a haunted train ride that will cause nightmares, Rails to the Darkside.

And while you might think, hmm trains, this must be for kids, you are sorely mistaken. Rails to the Darkside is great at using darkness, sounds, and spooky characters to really get you screaming.

NOTE : This event is only open to those aged 16 and over. 

Rails to the Darkside @ the Connecticut Trolley Museum 58 North Rd East Windsor

What will you do in Connecticut in the Fall?

Let me know what your favorite thing to do in Connecticut in the Fall is in the comments below.

For more fun things to do in the Fall, check out my posts about New England in the Fall and Where to Visit in the Fall in the USA .

About the author

Meg Frost is a Boston-based travel blogger that helps people embrace technology to make vacation planning and traveling wicked easy, affordable, and fun.

She holds an M.A. in Journalism from Northeastern University and B.S. in Communication & American Studies from University of Miami.

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This post was originally published on September 7, 2021. It was last updated August 17, 2023.

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Home » Blog » Ultimate Connecticut Fall Foliage Road Trip Guide

Ultimate Connecticut Fall Foliage Road Trip Guide

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As the leaves begin to change and the temperatures start to cool, it’s the perfect time to plan a trip to chase the fall foliage. Connecticut has some of the most stunning fall colors on the East Coast, making it the perfect place for a fall colors getaway.

We’ve chased fall foliage in the USA as travel photographers for the past 3 years now, and can honestly say Connecticut is so underrated. With fewer crowds than the rest of New England and equally as incredible colors, Connecticut is the perfect destination for those looking to take in all the vibrant leaves this year.

In this ultimate Connecticut fall foliage road trip guide, we’re sharing our top Western Connecticut fall foliage hikes, viewpoints, bridges, and scenic drives.

Planning Your Connecticut Fall Foliage Road Trip

Before getting into the details, when heading to explore Connecticut this fall, please make sure to follow all the Leave No Trace principles to keep Connecticut beautiful! Stick to the trails, take your trash, keep wildlife wild, be fire aware, and share the outdoors respectfully. Especially during peak foliage season, the New England region sees a lot of crowds, so we can all do our part to keep the state as clean and preserved as possible for others to enjoy in the future. 

Here are our top tips for planning your own fall foliage road trip around the gorgeous state.

Best Time to Visit Connecticut for Fall Foliage 

Historically, the best time to visit Connecticut for leaf peeping is mid-October to early November. Each year, foliage conditions do vary based on weather, drought, and storms, so it’s important to consistently track the foliage before you go. The key to a perfect fall foliage road trip around this area of New England is to be as flexible as possible with your itinerary since peak season can come and go very quickly. 

Our biggest tip is to keep an eye on fall foliage trackers as they are updated each week, and to check on Instagram to see live updates from those visiting in the area in terms of color levels. The Connecticut Department of Energy and Environmental Protection offers a weekly update on the status of fall foliage throughout the state.

Leave Room for Leaf Peeping Spontaneity  

Make sure to leave time to explore random scenic byways, public roads, and/or lakes you may stumble upon! We found so many incredible pops of fall foliage color that we didn’t originally have on our itinerary by intentionally getting lost and spontaneously following the colors as we encountered them. 

How to Get Around Connecticut

Although there is public transportation available, we’d highly recommend renting a car or Turo for your Connecticut fall foliage road trip. Having a car gives you the flexibility to adjust your plans if the fall colors aren’t optimal in certain areas at particular times. 

Keep in mind that the New England region sees an incredible amount of people during the fall season, so making a car rental reservation in advance is definitely the move. We’d also recommend the same advice for booking accommodations – the earlier, the better!

Wildlife on Connecticut Fall Foliage Hikes

The north western side of Connecticut has a ton of wildlife. You will likely be hiking in bear territory during this road trip, so make sure to be bear aware and follow all recommended precautions while out in the forest. This means:

• Know bear behavior : Learn about the behaviors and habits of bears in the area you will be visiting. This includes knowing what bears eat, where they live, and how they behave around humans.
• Stay on designated trails: One of the best ways to stay safe around bears is to avoid them altogether. Stay on designated trails, make noise while hiking, and keep a safe distance from bears if you do encounter them.
• Store food properly : Bears have a strong sense of smell and are attracted to food. Store food and garbage in bear-resistant containers or hang them from a tree at least 10 feet off the ground and 4 feet away from the trunk.
• Use bear spray : Bear spray is a deterrent that can be used in case of a bear encounter. Keep it easily accessible and know how to use it before you need it.
• Respect bear habitat: Avoid hiking or camping in areas where bears are known to be active, especially during mating season or when bears are raising their cubs.
• Travel in groups: Bears are less likely to approach groups of people than individuals, so it’s safer to travel in a group.

By being bear aware and taking these precautions, you can reduce the likelihood of encountering bears and stay safe in bear country.

Drone Photography Regulations in Connecticut

As photographers, it’s important to note that Connecticut unfortunately strictly prohibits the operation of drones in all State Parks and State Forests. You may apply for a special use permit; however, don’t plan on using your drone to capture the beautiful foliage in any of these regions.

You are able to use it throughout the state off of those state owned premises though as long as you have the proper certifications, licenses, and are following local regulations. Furthermore, for our top drone recommendations, check out our camera gear guide .

Best Ways to See The Fall Foliage in Western Connecticut

Scenic leaf peeping drives in western connecticut.

Western Connecticut is known for its stunning fall foliage, and there are many scenic drives that offer the perfect opportunity to enjoy the colorful autumn landscape. In our opinion, driving through Connecticut’s various state forests is one of the best ways to catch the fall colors in action. Some of the forest roads have the best, most uncrowded and untouched views of the foliage. Mohawk State Forest and People’s State Forest were two of our favorites for driving around and taking photos of the leaves. 

Here are some of the other top leaf-peeping scenic drives in Western Connecticut:

• Litchfield Hills Loop : This scenic drive takes you through some of the most picturesque towns and countryside in the Litchfield Hills region. Start in New Milford and follow Route 67 through Bridgewater, Roxbury, and Washington. The drive offers stunning views of rolling hills and colorful foliage, as well as charming New England towns with historic homes and farms.
• Mohawk Trail: This next scenic drive takes you through the rugged and scenic northwest corner of Connecticut. Start in Cornwall and follow Route 4 through Goshen, Litchfield, and Torrington. The drive offers stunning views of fall foliage, as well as historic sites and state parks.
• Housatonic Valley Heritage Loop: This scenic drive follows the Housatonic River and offers stunning views of the autumn landscape. Start in New Milford and follow Route 7 north through Kent and Sharon. The drive takes you through quaint towns and countryside, and offers plenty of opportunities to stop and take in the scenery.

Best Hikes to See Fall Foliage in Connecticut

Connecticut is home to many state parks and forests that offer great opportunities for hiking and exploring. Something super unique to Connecticut’s fall foliage hikes is how you can find some incredible leaf peeping along hikes to old abandoned towers and castles! We had never seen anything like this before coming from the West Coast. 

When heading out on these hikes, be sure to wear sturdy hiking shoes and bring plenty of water and snacks.

Haystack Tower

Enjoy a short scenic walk through the fall colors up to Haystack Mountain Tower. After about a 10-20 minute walk, you’ll reach Haystack Tower, which was built in 1929 as a fire lookout tower. The tower is 34 feet tall and offers 360-degree views of the surrounding countryside, including the Berkshire Mountains to the north and the Connecticut River Valley to the south.

The Haystack Tower Trail Yellow Loop is about 1.8 miles round trip with 505 ft. of elevation gain. We’d recommend this hike to anyone as it’s fairly short and family friendly.

Mount Tom State Park Tower

The Mount Tom Tower Trail was our favorite of the towers that we hiked to in Western Connecticut. It’s a 1.3 mile out and back trail with 337 ft. of elevation gain. The Mount Tom Tower hike takes you up a small incline to overlook a gorgeous lake below. Once you reach the summit, you’ll be rewarded with stunning panoramic views of the surrounding area. This region had great fall colors for mid-October.

Make sure to download the trail data ahead of time. When it is leaf peeping season, this trail can disappear as fallen leaves completely cover it and is slightly harder to follow. We’d recommend using All Trails or Gaia. Overall, it’s a great hike for anyone looking for a rewarding view of the Connecticut countryside.

Castle at Talcott Mountain State Park

Talcott Mountain State Park is one of the most popular state parks in Connecticut, and for good reason. Hike up to Talcott Mountain’s Heublein Tower by taking the Yellow Trail . Enjoy getting immersed in the beautiful foliage during the first half of the uphill climb on the hike. Once you reach the top of the trail, the tree line opens up for some incredible views of the hills all the way up until you reach the tower.

The hike is a 2.5 mile round trip loop hike with 245 ft. of elevation gain. Be aware that the hike starts with a fairly steep first half, but it flattens out considerably after the first mile.

Jessie Gerard Trail

Located in the People’s State Forest, the Jessie Gerard Trail is one of the best hikes in Connecticut for leaf peeping. Rated as moderate with some incline, the views up at Chaugham Lookout are unparalleled, especially if you catch it when the leaves are peaking! 

Make sure to start the trail earlier in the morning since there is a limited amount of parking available. Also, make sure to wear proper hiking shoes and, if you like, bring hiking poles, since the trail is fairly slippery next to the flowing rivers.

Chauncey Peak Trail

The Chauncey Peak Trail is a 2.2 mile loop that gives you stunning views above the tree line of the reservoir in Meriden. We’d recommend doing the trail counter clockwise to avoid having to go down the steeper rock walls, although this does mean that most of your elevation gain is in the beginning of your hike.

We’d recommend going at sunrise or sunset to capture the leaves here. We went at sunset and it was perfect for prime golden hour photos of the area. 

Macedonia Brook State Park

Macedonia Brook State Park in Connecticut is a great destination for viewing fall colors. The park boasts over 2,300 acres of forest, including a mix of hardwood and evergreen trees. There are several hiking trails throughout the park that offer scenic views of the surrounding hills and valleys, and the fall foliage can be particularly stunning.

Popular trails include the Blue Blaze Trail, which follows a stream through a hemlock grove, and the Cobble Mountain Trail , which offers panoramic views of the surrounding area. Additionally, there are several picnic areas in the park where visitors can relax and enjoy the fall colors.

Other Stops to Add to Your Connecticut Fall Foliage Road Trip Itinerary

Matthies Memorial Park in Beacon Falls

This is one of the most unique places to see fall colors. There’s an abandoned house in the middle of the lake here which makes for incredibly picturesque photos when the surrounding leaves are changing colors. 

Hidden Valley Preserve & Thoreau Bridge 

The Thoreau Bridge is a beautiful old 134 foot long suspension bridge in Hidden Valley Preserve. You can add it as a part of your hike to the Memorial Bridge following this trail. The bridge has inscriptions with famous quotes from the late author and is a hidden gem among the fall foliage lookouts in Connecticut. 

Bulls Covered Bridge

The East Coast is home to various covered bridges throughout the New England region. The Bulls Covered Bridge is right next to the Kent Falls State Park Area that was built back in 1842. It’s one of Connecticut’s few remaining functional covered bridges.

Lovers Leap Bridge

Lovers Leap Bridge is a very photogenic red lenticular truss bridge over the Housatonic River located in Lovers Leap State Park in New Milford, Connecticut.

Dennis Hill State Park

Dennis Hill State Park in Connecticut is a great spot for viewing fall colors. The park is located on a hilltop and offers panoramic views of the surrounding countryside, including the Housatonic River Valley and the Berkshire Mountains. You can also take a short walk to the summit for even more expansive views.

Finalizing Your Fall Colors Trip to Connecticut

Of course, there are many other beautiful hikes, scenic drives, and bridges in Connecticut to catch the changing leaves. However, if you only have a weekend or a few days, this guide is perfect for a quick road trip to see some of the highlights. 

If you have more time to explore western Connecticut, you can add on hikes such as the Sleeping Giant Trail, Bear Mountain, Rattlesnake Cliff, Castle Craig and more hidden gems around the area to extend your leaf peeping adventure. 

Overall, you should definitely add a Connecticut Fall Foliage Road Trip to your bucket list. Enjoy getting immersed in the beautiful yellows and reds. For more information on planning your fall colors activities, check out CTvisit for more fall trip planning resources. Planning on visiting the rest of New England for your fall colors road trip? Check out our leaf peeping guide to New Hampshire too!

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10 Perfect Places To Celebrate Fall In Connecticut

Looking to enjoy all the beauty and fun of the fall season in Connecticut? Then check out these incredible towns and attractions.

A celebratory fall getaway is often one for the books. This is especially true if you happen to be visiting the stunningly beautiful Nutmeg or Constitution State. Around this time of year, most touristy spots shed their summer skin and become almost like sleepy ghost towns ( ever been to the actual Sleepy Hollow? ) waiting for the next rush.

But savvy travelers and autumn lovers know this is the best time to get out there to see, do, and be. So whether you're looking for wholesome family fun, festivals, leaf peeping, outdoorsy activities , renowned comfort food, or some chills and thrills, Connecticut has it all.

That said, here are the ten perfect places to celebrate fall in Connecticut.

10 Harwinton

At first glance, this little town in Litchfield County may not seem like much, but upon further inspection, fall lovers will quickly note the abundance of autumn activities in and around this city.

What's more, the fall foliage in this area is downright superb.

The quaint town of Harwinton is the perfect location to get festive in, thanks to its nearby breweries, delicious eats, Gypsy Cakes , and ample festivities. While visiting, make sure to check out the annual Harwinton Fair for some fall-style fair fun, live music, wood chopping competitions, magic shows, and more.

9 East Haddam

There are two great reasons to head to East Haddam this fall— Devil's Hopyard State Park and Gillette Castle State Park .

Not only does the Devil's Hopyard offer visitors some incredible autumn views, but there is also a little something for everyone, including hiking, biking, lovely little picnic areas, and fishing.

The Devil's Hopyard even has a few campsites, so pitch a tent, build a fire, and get ready for some spooky time in this park.

For travelers looking for something more storybook and picturesque, Gillette Castle State Park is definitely for you with its intricate medieval fortress and one-of-a-kind views of shimmering gold, vibrant red, and burnt orange foliage.

8 New Canaan

Yet another place for autumn lovers is none other than New Canaan, CT. This fall destination is known for its history, modern architecture, gorgeous outdoor spaces like Waveny Park and New Canaan Nature Center , plus a plethora of seasonal festivities.

For instance, the New Canaan Nature Center Fall Fair , that's held every October, only gets bigger and better each year.

Fall fairgoers can celebrate the changing of the seasons with family-friendly activities like a traditional corn maze, an apple slingshot event, a spooky stroll, and pumpkin decorating.

There are also fire truck rides, zip lining, and carnival rides for the more adventurous souls.

7 Southington

A visit to Southington is definitely in order if you love scenic views, hauntingly interesting nearby castles like Castle Craig , expansive parks with fantastic foliage only a few minutes away ( Hubbard Park in Meriden, CT ), and of course, apples. Yes, that's right, apples.

This lovely city in CT is the proud host of The Southington Apple Harvest Festival . This is the event of all events for apples and people who love them.

With over 100,000 visitors annually , this family-oriented celebration/harvest extravaganza is reason enough to check out this corner of CT this fall.

Related: Connecticut Has The Second-Best Pizza In The U.S., And You Should Try These Dishes While You're There

Another small town that knows how to do fall right is Lebanon, CT . With ample fall activities within city limits as well as nearby, this is an excellent choice for anyone looking to celebrate fall the old-fashioned way.

Here, visitors can enjoy incredible farmers' markets, the more than a month-long Connecticut Renaissance Faire , pumpkin picking, and recreational fun in any of this city's several surrounding state parks.

Lebanon also has two fantastic in-city state parks—Mooween State Park and Pomeroy State Park—that are great for some fall-time fishing, hiking, hunting, boating, and so much more.

Related: The Ultimate East Coast National Parks Road Trip

5 Bethlehem

When you think of fall, chances are you conjure up images of cozy sweaters, pumpkin spice everything, bonfires, and garlic dishes galore.

At least that's what people in Bethlehem, CT see, and at the annual Connecticut Garlic & Harvest Festival in early October , visitors should expect nothing less.

A fun time for the whole family, this garlic party has a delicious variety of garlic dips, spreads, cheeses, and oils—all free to sample.

Plus, there are live garlic cooking demonstrations and musical performances. Festival goers will also notice a large selection of other fall-time veggies and produce—but it is clear who the star is here.

There are also a variety of other amazing autumn activities to check out while visiting if garlicky goodness is not your thing.

4 Glastonbury

Leaf peepers looking for even more fall-time fun and celebrations needn't look any further than Glastonbury .

This CT town also has an annual Apple Harvest & Music Festival with countless food trucks serving up tasty eats, a variety of harvest-style fun, live music, apple everything, and even a 5K road race .

Admission is also free to the Glastonbury Apple Harvest & Music Festival , so there's really no reason not to go.

Besides this significant event, Glastonbury is known for its incredible weekend apple picking, local farm goodies, fall happenings at The Old Cider Mill , and autumn pop-up sales/fairs.

3 South Windsor

Alternatively, for fall travelers looking for more small-town charm with fewer festivals, then South Windsor, CT is for you.

Visitors can enjoy a peaceful day at Desmond's Pond, marvel at the town streets lined with fall foliage, and stop by The Wood Memorial Library & Museum .

If you're feeling a bit outdoorsy, you can go zip-lining and maybe even play a game of golf while enjoying this town's perfect autumn weather.

Of course, there is an annual apple festival if you secretly crave some low-key apple-related fun or yummy apple cider donuts.

But, overall, if you prefer to celebrate fall more reflectively, this idyllic town can definitely accommodate.

2 Wallingford

For anyone looking to celebrate fall with the holidays in mind, then Wallingford, with its renowned Trail of Terror haunted hour tour, is definitely a must-see.

With more than a few safety guidelines in place, this bone-chilling display of things that go bump in the autumn night isn't for the timid or those who scare easily.

So, if this sounds like your type of fall celebration, then you should check out this spooky town and this particular haunted attraction.

Thrill seekers can easily make this a fall getaway to remember by sticking around for a few days and enjoying the many other ghostly activities in and near Wallingford or throughout Connecticut.

Finally, Riverton is your quintessential fall town in Connecticut, with something for everyone.

Besides wonderful fall county fairs in October, an abundance of wildlife, forested land, and recreational activities, Riverton has ample green spaces that allow visitors to truly reconnect with nature in one of the best seasons around.

So if you have always wanted to experience fall in a charming East Coast town that still has general stores, lovely rivers, friendly townsfolk, harvest celebrations, and the occasional wood chopping event, then this is the place for you.

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Connecticut Fall Foliage Guide: Best Places to Experience the Autumn Colors and Activities (and Eat Cider Donuts!)

By Helene Sula

Fall is a magical time of year in Connecticut, with vibrant shades of red, orange, and yellow blanketing the state's hills and valleys. As the temperatures drop and the days grow shorter, the trees shed their leaves in a spectacular display of nature's beauty.

If you're planning a fall foliage tour of New England, Connecticut is a must-visit destination. From scenic drives and hiking trails to pumpkin patches and apple orchards, there are plenty of ways to experience the autumn colors in this charming state.

In this guide, we'll explore some of the best places to see fall foliage in Connecticut and offer some tips for planning your trip.

Best Places to See Fall Foliage in Connecticut

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As a fall foliage enthusiast, I was thrilled to visit Connecticut during the peak of the autumn season. Driving through the picturesque towns and scenic routes, I couldn't help but notice the abundance of grand mansions and elegant estates that dotted the landscape. I couldn't help but wonder if everyone in Connecticut was rich.

But Connecticut isn't just for the wealthy. There are plenty of affordable ways to enjoy the fall foliage, from apple picking to hiking. One of my favorite experiences was visiting the local apple cider donut shops. These cozy little spots offered warm, fresh donuts and delicious cider that perfectly complemented the crisp autumn air.

I also couldn't resist the temptation to explore Yale University's campus in New Haven. Sneaking around the historic buildings and beautiful courtyards, I felt like I was in a Harry Potter movie .

But the real highlight of my trip was the breathtaking fall foliage. Connecticut's countryside was transformed into a canvas of vibrant reds, oranges, and yellows, creating a truly magical atmosphere. I made sure to visit some of the best places to see the foliage, including the Litchfield Hills and the Connecticut River Valley.

Overall, my trip to Connecticut was an unforgettable experience. With its beautiful fall foliage, charming towns, and delicious treats, Connecticut is a must-visit destination for anyone looking to enjoy the autumn season.

The homes are all so beautiful, I wondered if everyone is wealthy in Connecticut?!

As I explored the quaint towns and charming villages of Connecticut, I couldn't help but feel like I was on the set of Gilmore Girls. From the picturesque town greens to the cozy coffee shops and bookstores, it was easy to imagine Lorelai and Rory strolling down the streets, chatting about life and love. The fall foliage only added to the idyllic atmosphere, with the colorful leaves falling gently to the ground and creating a romantic ambiance. It was a surreal experience, and one that made me appreciate Connecticut's small-town charm and beauty even more.

Located in the northwest corner of the state, the Litchfield Hills region offers some of Connecticut's most picturesque fall scenery. Drive along Route 7 or Route 202 for stunning views of the rolling hills and dense forests, and be sure to stop in the quaint town of Litchfield for some shopping and dining.

The northeastern part of Connecticut, known as The Quiet Corner, is a peaceful and charming region with plenty of fall foliage to enjoy. Take a scenic drive along Route 169, which passes through several historic villages and offers views of the colorful forests and farmland.

The Connecticut River Valley is another must-visit destination for fall foliage enthusiasts. Take a cruise along the river for a unique perspective on the autumn colors, or hike one of the many trails in the area for an up-close look at the foliage.

The Mystic Country region is a popular tourist destination year-round, but it's especially beautiful in the fall. Take a stroll through one of the region's many historic villages, or explore the scenic back roads for stunning views of the foliage.

Mohawk State Forest is another beautiful destination in Connecticut for outdoor enthusiasts during the fall season. The forest covers over 3,000 acres and offers a variety of hiking trails that wind through the colorful foliage. Some of the most popular trails include the Mohawk Trail, the Mattatuck Trail, and the Mohawk Pond Loop.

In addition to its natural beauty, Mohawk State Forest is also home to several historic sites, including the remains of an 18th-century iron-making furnace and the Indian Council Caves, which were once used by Native Americans for shelter.

For those interested in exploring Connecticut's cultural and academic side, a visit to Yale University in New Haven is a must. Yale is one of the oldest and most prestigious universities in the United States, and its campus is filled with historic buildings and beautiful courtyards that are perfect for a fall stroll.

One of the highlights of Yale's campus is the Beinecke Rare Book and Manuscript Library, which houses one of the world's largest collections of rare books and manuscripts. The library's iconic glass tower and unique architecture make it a popular spot for Instagram photos.

Another fantastic addition to the list of fall foliage spots is Kent Falls State Park in Connecticut. This park offers an idyllic setting for witnessing the beauty of fall. Here, you can wander across the covered bridge, hike the falls, and feel the mist on your face as water cascades 250 feet down on its way to joining the Housatonic River. It's a mesmerizing experience that will leave you in awe of nature's wonders. Be sure to add Kent Falls State Park to your itinerary and create unforgettable memories.

Connecticut is known for its delicious apple cider donuts, which are a must-try during the fall season. Fall in Connecticut is just something special! Here are five of the best places to get apple cider donuts in Connecticut:

Hogan's Cider Mill is another must-visit spot for apple cider donuts in Connecticut. Located in Burlington, Hogan's has been producing cider since 1912 and is a popular destination for locals and tourists alike. Their apple cider donuts are made fresh daily and are a fan favorite.

In addition to their delicious donuts, Hogan's Cider Mill is also an Instagrammable location, with a charming rustic atmosphere that is perfect for fall photos. The mill's picturesque setting, with its old-fashioned equipment and sprawling apple orchards, makes for a perfect backdrop for capturing memories with friends and family.

Hogan's Cider Mill is a great place to visit for anyone looking to enjoy the autumn season in Connecticut. With its delicious cider donuts and scenic surroundings, it's no wonder why it's become a favorite spot among locals and visitors alike.

Located in Old Mystic, B.F. Clyde's Cider Mill is the oldest steam-powered cider mill in the United States. Their apple cider donuts are made with their signature apple cider and are a fan favorite. It's got a great wrap-around porch and places to hang out!

Lyman Orchards is a popular apple orchard in Middlefield that offers a variety of fall treats, including their famous apple cider donuts. These donuts are made fresh daily and are a must-try for anyone visiting Connecticut during the fall.

Bishop's Orchards in Guilford is another popular spot for apple cider donuts. Their donuts are made with their own apple cider and are available in regular or mini sizes.

Beardsley's Cider Mill & Orchard in Shelton has been in operation since 1849 and is a favorite among locals. Their apple cider donuts are made fresh daily and are a perfect snack while exploring the orchard.

Rogers Orchards in Southington is a family-owned farm that has been operating for over 200 years. Their apple cider donuts are made with their own fresh-pressed apple cider and are a delicious fall treat.

Connecticut is not only known for its stunning fall foliage and delicious apple cider donuts, but it also offers a variety of fall-themed activities that are perfect for all ages. Here are a few activities to consider when planning your fall trip to Connecticut:

Located in Mystic, Olde Mistick Village is a charming outdoor shopping center that offers a variety of fall-themed activities, including pumpkin painting, scarecrow making, and apple cider tastings. The village also has several unique shops, such as “The Cloak and Wand,” a Harry Potter-themed store that sells merchandise and offers wand-making classes.

After stopping here, make sure to check out the charming town of Mystic and the one and only “Mystic Pizza” from the Julia Roberts movie!

Strawberry Hollow Farm in Glastonbury is a family-owned farm that offers fall activities such as pumpkin picking, hayrides, and corn mazes. The farm also has a market that sells homemade pies, apple cider donuts, and other fall treats.

Fall is the perfect time to explore Connecticut's wine country. The Connecticut Wine Trail offers tours of the state's wineries and vineyards, which are surrounded by colorful foliage and offer stunning views of the countryside.

Connecticut is home to several fall festivals that offer a variety of activities, including live music, food, and craft vendors. Some of the most popular fall festivals include the Durham Fair, the Apple Harvest Festival in Southington, and the Garlic & Harvest Festival in Bethlehem.

Thorncrest Farm is another must-visit spot in Connecticut for fall-themed activities. Located in Goshen, Thorncrest Farm is a family-owned farm that offers a variety of activities for visitors, including hayrides, corn mazes, and pumpkin picking. The farm also has a store that sells homemade ice cream, artisanal cheeses, and other locally sourced products.

One of the highlights of Thorncrest Farm is their “Cowtoberfest” event, which takes place every October. This event offers a range of fall activities, such as cow milking demonstrations, live music, and hayrides. Visitors can also sample Thorncrest Farm's famous raw milk, which is unpasteurized and sold in glass bottles.

Aside from its fall-themed activities, Thorncrest Farm is also known for its commitment to sustainable farming practices. The farm uses solar panels to power its operations and has implemented several other environmentally friendly initiatives.

If you're looking for a fun and educational fall activity in Connecticut, be sure to add Thorncrest Farm to your list. Whether you're looking to pick pumpkins, sample locally made cheese, or learn more about sustainable farming, Thorncrest Farm offers something for everyone.

For those who love a good scare, Connecticut has several haunted attractions that are open during the fall season. The Haunted Graveyard at Lake Compounce in Bristol, Fright Haven in Stratford, and Trail of Terror in Wallingford are just a few of the many haunted attractions in the state.

These are just a few of the many fall-themed activities that Connecticut has to offer. Whether you're looking for a family-friendly outing or a spooky adventure, there's something for everyone to enjoy during the autumn season in Connecticut.

A visit to Mark Twain's Home in Hartford is a must for any literature enthusiast visiting Connecticut during the fall season. The home, also known as the Mark Twain House & Museum, was the former residence of author Samuel Clemens, better known by his pen name, Mark Twain. The house is a stunning example of Victorian Gothic architecture and is filled with original furnishings and artifacts from the author's life.

Visitors can take a guided tour of the house, which includes a visit to Twain's writing studio, where he wrote some of his most famous works, such as “Adventures of Huckleberry Finn” and “The Adventures of Tom Sawyer.” The museum also offers exhibits on Twain's life and legacy, as well as educational programs for visitors of all ages.

In addition to the house and museum, the Mark Twain Home also offers a range of fall-themed events and activities, such as a pumpkin patch and a Halloween-themed tour. The house's location in Hartford, Connecticut's capital city, also makes it a great spot for exploring the city's many historic sites and attractions.

Overall, a visit to Mark Twain's Home is a fascinating and educational experience for anyone interested in literature, history, or architecture. With its beautiful Victorian Gothic style, original furnishings, and historical significance, the home offers a unique glimpse into the life and legacy of one of America's most iconic authors.

• Timing is everything: The peak foliage season in Connecticut typically runs from mid-October to early November, but it can vary depending on the weather conditions. Check foliage reports and plan your trip accordingly.
• Get off the beaten path: While the scenic drives are a great way to see the foliage, don't be afraid to explore some of the lesser-known areas for a more authentic experience.
• Take advantage of the harvest: Fall in Connecticut is all about apples, pumpkins, and other seasonal treats. Visit a local farm or orchard to pick your own produce or sample some fresh cider.
• Dress in layers: The fall weather in Connecticut can be unpredictable, so be sure to bring layers and dress for the cooler temperatures.

Start your day at B.F. Clydes for incredible hot cider donuts! This is a beautiful spot.

Spend the morning in Mystic, Connecticut, a charming seaside town known for its historic ships, museums, and shops. Have a slice of pizza at Mystic Pizza.

Next, venture to Strawberry Hollow Farm, where you can explore this adorable farm, take pictures with pumpkins and explore the shop.

Visit the prestigious Ivy League university, Yale Campus, for a walking tour of the campus and to admire the architecture. Tours are free!

You can explore New Haven and Enjoy a delicious dinner at a local restaurant, such as Union League Cafe, which serves classic French cuisine in an elegant setting.

Start the day with a tour of Mark Twain's home nearby in Hartford.

Take a scenic drive through the Litchfield Hills, which offers some of the best fall foliage views in the state. Head to Kent Falls State Park for some beautiful views!

Stop for lunch at a local restaurant, such as the West Street Grill in Litchfield, which offers farm-to-table cuisine and a cozy atmosphere.

I really love exploring this town!

Explore more fall foliage around Litchfield, or head to Washington, Connecticut for scenic waterfalls. Check out Steep Rock Preserve for epic views.

Head to Maple Bank farm for New England maple syrup!

If you have time, head further south for Silverman's Farm in Easton, Benedict's home and garden, or Plasko's farm and creamery.

Connecticut is so easy to drive and explore!

Connecticut is a fantastic destination for anyone looking to experience the magic of fall foliage. Whether you're driving along scenic routes, hiking through forests, or simply strolling through historic villages, there are plenty of ways to soak up the autumn colors in this beautiful state.

With this guide, you'll be well-equipped to plan your own Connecticut fall foliage tour and create memories that will last a lifetime. So what are you waiting for? Start planning your trip today and get ready to witness nature's most stunning display of the year!

MEET THE AUTHOR

Helene Sula

I believe that one trip can change your life. It did for me. I'm a self proclaimed home body that quit her job, moved abroad, and more often than not, lives out of a carry-on bag. If I'm not traveling, I'm most likely re-reading Harry Potter or watching "Midnight in Paris" while snuggling my dogs. I'm a digital marketing expert who turned my love of travel into a full-time career. And I help others do it too.

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The 10 Best Things to Do During Fall in Connecticut

Posted by Sarah Lamagna October 15, 2022 Updated January 16, 2024

Grab your flannel and Blundstone boots to discover the joys of autumn in Connecticut.

Most people think of yacht clubs and Yale University when Connecticut is mentioned. But the third smallest state packs a lot of punch when the autumn months arrive. While most folks in the New England area might be taking a scenic drive in New Hampshire to view epic fall foliage, be the smarter person and stick around Connecticut to experience a true New England autumn.

Whether you want to venture through a real-life castle, drink yourself silly on hard cider, or don some kilts at a Highlands festival, Connecticut is the place for you this fall.

Related Read:   9 Romantic Getaways in Connecticut to Turn up the Heat

1. Pick Some Apples.

There is nothing more iconic than picking apples during the autumn months in New England. Luckily, the soil and weather that graces Connecticut during these months are ideal for apple orchards. Usually, apple picking season begins in mid-August into early September (depending on the orchard) although most visitors tend to visit in late September.

Visitors and residents alike can choose from a plethora of orchards across the Constitution State. One of the favorites (and most famous) is Lyman Orchards . As a frequent name on many “top 10” lists, Lyman Orchards built up its name since 1741 when John and Hope Lyman bought 37 acres of land where the Homestead now sits.

During the summer months, you can get lost in a sunflower maze and pick whatever fruit might be blooming. But during the autumn months, pick from several varieties of apples and then grab a pumpkin from the pumpkin patch on your way out. There is also a corn maze and a haunted orchard walk for those who need a bit more fright in their lives.

2. Sip Some Brew at a Cidery.

Move over craft beer and distilleries and make room for the growing sensation of cideries which has spread throughout Connecticut . The New England Cider Co. has autumn-filled flavors including pumpkin- and cranberry-infused ciders.

One of the most unique cideries is Spoke and Spy Cider which offers a chai-inspired cider perfect for a cool, autumn day. Or head to Yankee Cider Company , where they focus on a New England-style cider meaning its drier with a lower sugar content.

3. Explore the Town of Mystic.

Julia Roberts made the small town of Mystic famous for her role in Mystic Pizza — which is an actual pizza shop in town — however, Mystic has far more reasons to visit than a 1980s film.

Create a personalized Oktoberfest with the 32 taps that are constantly changing at the Jealous Monk . Attend the annual Garlic Festival in mid-September which is one of the most popular events. During the entire month of October, scarecrows line the walkways of Olde Mistick Village .

Don’t forget to visit the oldest steam-powered cider mill in the United States at B.F. Clyde’s Cider Mill . Order the donuts, you won’t regret it.

4. Peep Some Fall Colors.

No matter where you live or are staying in Connecticut , the fall foliage around New England cannot be compared. What makes New England incredibly unique is the sheer diversity of tree species that produce all types of color throughout the autumn season.

There are several scenic drives you can take to view some of the best colors, but the best way to view them is to get out on foot. Two of the best hikes to experience the state’s fall foliage are Bear Mountain (the highest peak) and Jessie Gerard Trail which boasts sweeping views of thousands of acres of forest.

5. Go to Scotland Without Getting on a Plane.

The small town of Scotland has more than just the name in common with the country of Scotland. It is also home to Connecticut’s Highland Games Festival . There is no need to jump on a plane and spend an exorbitant amount of money in a foreign country to view some men in kilts. The big festival occurs at the beginning of October every year and invites those who long for step-dancing and caber-tossing to enjoy the festivities.

Other events and activities include a fiddler’s workshop, a “bonnie knees” contest, herding dog demos, and some good old-fashioned harp playing. You will be aching for a wee dram at the end of the day so check out the multitude of distilleries in the state.

6. Check Out Some Scarecrows.

You won’t find any yellow brick roads along the streets of Old Wethersfield. But what you will find is a boat load of hand-crafted scarecrows created by local artists, families, and shopkeepers. The 60+ scarecrows that line the streets vary from spooky to down-right hilarious.

You can also view Scarecrows in the Meadows in Litchfield. This annual event invites everyone in the community to explore more than 50 scarecrows and then vote on their favorites.

7. Live Like a Royal at Gillette Castle.

Nestled among the chain of hills called the “Seven Sisters,” Gillette Castle’s beauty shines over the Connecticut River. Named after William Hooker Gillette, famed director, playwright, and actor, the castle’s eerie, gothic architecture has captivated crowds for decades. Gillette’s most famous role was Sherlock Holmes and showed the same type of genius designing his home as Holmes’ did with solving crimes.

The autumn brings colorful leaves along the miles of trails throughout the state park. But it also brings a sense of spookiness to the landscape with its medieval architecture despite there being no evidence of it being haunted.

8. Ride an Old-Fashioned Steam Train.

If you have never heard of the Essex Steam Train while in Connecticut, you have probably been living under a rock. Since 1868, the Valley Railroad Company has graced the landscape of Connecticut. Excursions by both train and boat run daily, there are several unique experiences they offer as well. Attend the “Boos, Brews, and BBQ” event where real ghost hunters lead attendees on a paranormal investigation across the station grounds.

You can also take The Salem Express for a family-friendly experience to welcome the famed Sanderson Sisters from Hocus Pocus to Essex. Even if you don’t go for a ride (although it’s highly suggested that you do!), even just viewing the steam train in action is a real treat.

9. Satisfy Your Sweet Tooth.

You don’t have to travel to Belgium or Switzerland to experience chocolate delicacies. Instead, Connecticut is home to a large array of chocolate artisans who love to share their passions of cacao with visitors from around the region.

Depending on your location, you can choose from several chocolate outlets along the Connecticut Chocolate Trail . Chocolatiers in southwestern Connecticut include Noteworthy Chocolates where you can have chocolate engraved to whatever you like. Le Rouge Handmade Chocolates in Westport has some of the most exquisite designs on chocolate and are true works of art.

Central Connecticut has Tschudin Chocolates and Confections and Sweet Cioccolata while the southeastern part of the state houses the Chocolate Shell and Mystic River Chocolate . There is no shortage of sweets to satisfy those who crave sugary goodness.

10. Don Your Medieval Armor and Vanquish Your Enemies.

Rewatch the entire series of Game of Thrones and grab your nearest sword to head to the Connecticut Renaissance Faire . Usually starting in early September and lasting through mid-October, the Renaissance Faire is great for the entire family.

Little ones will enjoy the Knights School where they can learn to be a squire or a full-fledged knight! Speaking of fledging, watch the Knightwings (aka birds of prey) dive through the air in their acrobatic flights. End your day with the classic jousting tournament where knights battle for a fair maiden. Be sure to check out the theme for the weekend you plan to attend in order to have the correct attire — although fun, it’s not required.

Explore New England in Autumn

Where to View the Best Fall Foliage in New England

15 Fantastic Things to Do in the Fall in Rhode Island

8 Beautiful Places to See Fall Colors in Maine

10 Things to Do in the Fall in New Hampshire

9 Must-See Waterfalls in Maine You Can Hike To

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Seen in: Connecticut , Fall Colors , New England , Northeast

Posted by Sarah Lamagna

Sarah is an ecologist-turned-freelance writer specializing in the ecotourism and slow/sustainable travel industry. Her bylines include The Denver Post, 5280 magazine, VeryWellFamily, Matador Network, and was an expert on NPR’s The Takeaway for her work on the wildfires in Colorado.

Fall Foliage 101: Why Do Leaves Change Colors in the Fall?

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New England Wanderlust

Connecticut , Fall , Maine , Massachusetts , New Hampshire , Rhode Island , Vermont  ·  June 7, 2023

The PERFECT New England Fall Road Trip Itinerary: 3, 5, 7, 10 & 12 Day Options! (2024)

There’s a reason why New England is world-famous for fall foliage, and if you’re looking to plan the most amazing New England fall road trip, you’ve come to the right place! I’ve been traveling throughout this region for over 15 years, and have done quite a few fall foliage road trips and even more fall getaways. It took me a while, but I’ve finally put together the perfect itinerary for you based on real experience.

This post details the best places to visit in New England during fall foliage season that are worth the hype, the best times to plan your road trip, and also, which places may not be worth your time. So, you can rest assured that you’re truly seeing the best of the best with my itinerary.

This itinerary is also geared toward first-timers and those looking to find the best foliage spots . If you’ve experienced New England in the fall season before, many of these locations and tips may already be familiar. However, I’ve also sprinkled in some insider tips, so it’s still definitely worth reading 😉

During this trip, prepare to see idyllic countryside landscapes, blazing fall color, beautiful covered bridges, charming towns, general stores, epic overlooks and hiking trails, and so much more. Basically, you’ll get your fill of New England charm right from the start, and it won’t stop until the trip is over. Sound good? Then let’s get started!

New England Wanderlust contains affiliate links, and is a member of the Amazon Services LLC Associates Program. We may earn a commission from any purchases you choose to make from our links, at no additional cost to you. For more information, please refer to our  Privacy Policy .

Tips For Planning A Trip To New England In The Fall

There are some important things to know before you begin to plan your perfect New England fall road trip, so let’s get that out of the way first 😉

The first thing you need to know is that foliage will peak in the northern areas first, then peak in the southern areas later . For that reason, I recommend that you start in the north if you can, especially for a longer trip, but it’s not always necessary for shorter trips.

If you’re planning a bucket list 2-week adventure, starting in the north is a good call because peak foliage can begin to diminish quickly, depending on the season and climate patterns. However, if you’re traveling for closer to a week, this won’t be as important.

I go into peak foliage times in each region in a bit, so definitely be sure to read that through, too!

Another important thing to know is that you should anticipate all kinds of weather. I’ve done many fall road trips through this region, and have had warm, sunny days, and trips where it rained almost every single day. I’ll go more into what to pack for this trip at the end of the post to help you prepare, but this is a good thing to be aware of.

Also, book in advance . I can’t stress this enough. Hotels and accommodations book out well in advance for fall foliage season in prime areas, and these prime areas are where you’ll be heading! If possible, begin to book your hotels at least 6 months in advance, but even 8 months is better. For reference, while I began to plan my Vermont fall road trip for the 2023 season, my favorite place to stay in Stowe, VT was fully booked during peak foliage weeks – in FEBRUARY. Yep, February.

Offline Google Maps! I can’t tell you how important this is! Even as recent as a fall 2022 road trip, I barely had service through much of New Hampshire and Vermont. I spent a lot of time just driving around hoping my service would come back, or asking people for directions the old-fashioned way. I usually offline maps, but totally forgot that trip, and it was a harsh reminder that this is a must-do.

Lastly, prepare to pay . Yes, the sad truth is that peak foliage season in New England is expensive, and it won’t be your most budget-friendly trip ever. There are ways to keep costs down, and I’ll go more into that later in the post as well, but generally speaking, this is an expensive time to visit New England – at least, where the foliage is the best 😉

What Is The Best Time To Visit New England For Fall Color?

In a nutshell, the last week of September, or the first week of October. However, it does vary depending on where you’re heading.

As mentioned before, the colors will begin to change in the northern regions first, and then the southern regions will follow later. Most people will choose to visit Maine, New Hampshire and Vermont during their New England fall road trip (and spoiler alert: this is also where I’ll be suggesting you go!), so this timeframe works very well for these areas.

The central part of Vermont will often peak right around Indigenous People’s weekend in October, and for a getaway to popular towns like Stowe and Woodstock, this is the perfect weekend to plan your trip.

Massachusetts often peaks right around Indigenous People’s weekend as well, with southern MA peaking a week or so later.

The greater Boston area, and Connecticut will peak mid-late October, depending on the year.

How Many Days Do You Need In New England In The Fall?

The great thing about New England in the fall is that you can easily do a weekend getaway and still pack a lot in, or you can plan an epic 12 day road trip for the ultimate adventure. And either way, it’s going to be incredibly memorable.

If you’re coming in from a distance, especially if you’re flying in, I would say 10 days is a great option, 12 days is even better, and 7 days is also wonderful. Of course, with 12 days, you’ll be able to see so much or plan extra time in some places. But even with 7 days, you’ll get to see quite a bit.

If you’re local to New England, and don’t have 10 days, 7 days is again a nice sweet spot. 5 days will also work in this case. And, as mentioned, even a weekend away will allow you to experience some of the best this region has to offer in the fall season.

The great thing about the best places for fall foliage are located in some of the smallest states, so you can cover a lot of ground in a short amount of time.

Best Places To See On A New England Fall Road Trip

While every New England state has something special to offer during fall foliage season, for the purpose of seeing the absolute best spots, I recommend sticking to Maine , Massachusetts , New Hampshire and Vermont . And flying into Boston.

Because these areas offer the most spectacular displays of foliage, most picturesque scenery, tons of things to do, and they’re all reasonable close to one another, allowing you to maximize your time.

Here’s why I don’t necessarily recommend states like Connecticut or Rhode Island if you have less than 10 days – they’re further away from the best places to see in the fall.

I truly love every single New England state, and I do really enjoy Connecticut in the fall. However, it’s so far west that you’ll spend more time driving to get there, and possibly forgoing some really spectacular places in Maine, New Hampshire, Massachusetts, and Vermont.

If you have 10 days or more for a New England fall road trip, then I would highly suggest you consider adding in the Litchfield Hills regions of Connecticut , which you’ll see I included in my itinerary. It’s also very close to The Berkshires region, so you can combine it with that part of the trip, depending on how much time you have. However, with less than 10 days, I personally don’t feel like it’s worth it. Especially for first-timers.

If you’ve already seen some of the places I’m recommending in this post, then definitely try to swing over to Connecticut and experience a new area during the fall!

If you have less than 10 days, you may even want to focus all your time on Vermont and New Hampshire. The reason for this is because some of the best places for fall foliage in Maine are further north. I think places like Acadia National Park are very worth seeing (and you’ll see I’ve incorporated it into some of my itineraries!). However, if you prefer a slower pace and less driving, Vermont and New Hampshire are the absolute best places to see .

Some Things To Know About My Itineraries

They all begin in Boston , assuming that’s where most people will fly into if visiting from a distance. If you fly into a different airport, or are driving in, you can easily adjust your plans as needed.

They’re done in true road trip style , meaning there’s a lot of driving, and mostly 1-night stays. There are some places I recommend 2 nights in, but you can adjust this based on your preferences. If you want to stay longer in one place, definitely go for it!

I give you options! Of course, I stand by all my suggestions ☺️ However, I know everyone has different travel styles and speeds, so I encourage you to to tailor this to what you think you’ll enjoy the most. I’ve given you suggestions on how to adjust the itinerary based on your preferences.

10 Day New England Fall Road Trip Itinerary From Boston

Okay, let’s get into my perfect New England fall road trip itinerary options! We’re beginning with my suggestions for an incredible 10 day adventure.

10 Day Road Trip Overview

Day 1 : Arrival In Boston Day 2 : Explore Boston Or Take A Day Trip To Salem Day 3-4 : Bar Harbor/Acadia National Park + An Optional Stop In Salem Day 5 : Jackson, NH Day 6 : Franconia, NH (Driving The Famous Kancamagus Highway To Get There!) Days 7-8 : Stowe & Woodstock, VT Day 9 : The Berkshires and/or Litchfield, CT Day 10 : Back To Boston + A Stop In Sturbridge, MA or Litchfield, CT

Breakdown Of The 10 Day Itinerary Option

Day 1: Arrival In Boston Take this time to arrive, get settled, and maybe take in a few sites around the city! Have some time on your first night here? Jump down to Day 2 for some suggestions on what to do!

Where To Stay In Boston:

• Luxury : The Langham
• Splurge : Boston Harbor Hotel
• Moderate : Revere Boston Common

Pro Tip On Fall Foliage In Boston : Foliage peaks later than the rest of the places listed in this itinerary – usually mid-late October. So while you probably won’t see peak foliage in Boston if you plan your trip for peak foliage in Vermont, New Hampshire and Maine, it may catch a glimpse of it on your back if you’re planning a longer trip! Or, you can leave the airport to immediately begin your drive to Maine, and plan to stay a night or two in Boston before you have to fly out.

Day 2: Explore Boston

Boston during the fall season has so much to see and do, but here are some highlights to consider if it’s your first visit:

• Public Gardens (very scenic garden area with a beautiful pond and pedestrian bridge (also makes for lovely photos!). This is a good spot for fall foliage in the city, too.
• Newbury Street for shopping
• The North End for history and food
• Beacon Hill for charming cobblestoned streets at the famous Acorn Street
• Take a food tour if it works with your schedule. There’s incredible food to be had in Boston, and taking a tour with a local expert is a great way to sample lots of delicious things in a short amount of time!

Click here to check out my post on the best Boston food tours!

Day 2: Optional Day Trip To Salem

If you would prefer to take a day trip to Salem, rather than stopping on your way to Acadia National Park, this is a great option! And really, there’s no right or wrong choice here – it just comes down to which you prefer.

Salem is an easy day trip from Boston without a car because of this convenient ferry! Click here to check out the Boston → Salem Ferry!

Psst! I have some helpful guides including planning the perfect Salem, MA day trip , and the best time to visit Salem if you need more information 😉

Day 3: Drive To Bar Harbor & Acadia National Park

Acadia National Park is one of the best things to do in New England year-round, so this is definitely a must if you’ve never been. It also offers some really wonderful foliage, and fall is my personal favorite season to visit for this reason.

This drive from Boston to Bar Harbor takes about 5 hours without stops, which is why I usually suggest you make a pitstop to break up your journey. I actually have some posts on stops you can make along the drive, so be sure to check those out below.

But since Salem is really the ultimate fall destination in Massachusetts, I suggest you pick that as a stop on the drive 🙂

Bar Harbor is the town adjacent to Acadia National Park , and where most people will choose to stay when visiting. Once you arrive, take some time to get settled, and then head out into downtown Bar Harbor to explore this charming seaside town, visit the shops, and grab a great dinner!

Where To Stay In Bar Harbor:

• Bayview Hotel . An oceanfront boutique hotel with awesome views. Perfect for a splurge on your trip!
• Bar Harbor Villager Motel . Clean, updated and spacious. Also, walkable to everything in town.
• Little Fig Hotel . A cute, modern boutique hotel walkable to town.

Here are some posts that will help you further plan this portion of your trip:

• Best Stops To Make Driving Boston To Portland, Maine
• Best Stops To Make Driving Portland to Acadia National Park
• The Perfect Acadia National Park Itinerary (read this one for more information on Bar Harbor and things to do!)
• Best Time To Visit Acadia National Park

Day 4: Explore Acadia National Park

Even in just 1 day, you can visit some of the best places in the park, and also some really wonderful fall foliage spots. Here how I suggest you plan your day:

If you’re up for it , starting your day with sunrise at the top of Cadillac Mountain is always incredible! It’s one of the first places in the U.S. to see the sunrise, depending on the time of year, and starting October 7 through March, it’s the very first spot in the country to see the sun come up. This will be great for fall foliage, too. You can also choose to do this the following morning before leaving.

Next, head to the Jesup Path scenic walk , which is especially beautiful in the fall season.

Then, park at the Sand Beach parking lot , and walk the Ocean Path for incredible views . This is 1-mile each way, but offers some of the most iconic views in the park, including the Otter Cliffs and Thunder Hole. It’s also flat and easy, making it very relaxing. Have your camera ready for this one!

For a more advanced hike with awesome foliage views, you can do the Beehive Trail from Sand Beach lot, too.

Continue on Park Loop Road to Jordan Pond House for lunch , and enjoy the views of the pond and mountains. You can also choose to walk around the pond if you have time after lunch.

For more foliage views, hike the Bubble Rock Trail after lunch.

Day 5: Drive To Jackson, NH + Spend The Night

Without stops, this drive takes about 4 hours and 15 minutes.

One stop I suggest making on the way if you enjoy local craft beer is the Oxbow Beer Garden in Oxford , ME . It’s got a very cool outdoor setting, and they have fantastic craft beer.

I recommend spending the night in Jackson because it’s a longer drive from Bar Harbor, and there are some fun things to do in the area. Also, there’s a very scenic drive called The Kancamagus Highway that’s stunning in the fall season with foliage, and I want to make sure you have time to drive it. But more on that in Day 6 🙂

Here are some fun fall things to check out in Jackson:

• The Cog : This mountain railroad takes you to the summit of Mount Washington, the tallest peak in New England! It’s about 45 minutes from Jackson, but you’ll drive through Crawford Notch State Park , which is very scenic, and The Cog is simply incredible in the fall season. If you leave Bar Harbor early enough and have time to do this, I highly recommend it!
• Honeymoon Covered Bridge & Flossie’s General Store
• Glen Ellis Falls
• The cute town of North Conway

Where To Stay In Jackson:

• Christmas Farm Inn (this place is super cozy!)
• The Inn At Thorn Hill & Spa

Option To Stay In North Conway : North Conway is only about 12-15 minutes from Jackson, so you can really stay in either. I think Jackson has better hotel options, and it’s a bit closer to The Cog, which is why I suggested you stay there. But either town works for your New England fall road trip!

Here are some fun things to check out in North Conway if you choose to visit:

• Cathedral Ledge Distillery
• Ledge Brewing Company (between North Conway and Jackson, technically)
• The cute downtown area and Zeb’s General Store (one of my all-time favorite general stores!)
• North Conway Scenic Railroad

Day 6 – Drive The Kancamagus Highway To Franconia, NH

The Kancamagus Highway (Route 112) is a scenic drive that’s regarded as one of the best drives for fall foliage, so this is something you’ll definitely want to do on your New England fall road trip. It connects the towns of Woodstock and Conway, so you can easily start this drive just a few minutes from Jackson or North Conway.

For this day, I suggest you get up early to make sure you have time to explore Franconia Notch State Park after driving The Kanc.

Tips For Driving The Kanc:

• Remember earlier in the post when I said you’ll lose cell service in much of New Hampshire and Vermont? Well, this is one of those drives where there’s no service, so offline your maps before starting!
• There are no bathrooms or gas stations on the drive, so plan accordingly.
• The Kanc takes about 45 minutes one-way without stops, but you’ll want to budget about 2 hours to make some stops at the overlooks.
• During the fall season, especially on weekends, it’s possible traffic could slow down as people try to pull in and out of the parking areas. Plan for some slower traffic.

Pro Tip : Before hopping onto The Kanc, there’s a great little place called Cheese Louise just before the entrance to The Kanc, and this is an awesome place to grab some food before the drive! Especially on a chilly, fall day, a grilled cheese sandwich totally hits the spot, right? 😍

Stops To Make On The Kanc (in order from Conway to Woodstock):

• Albany Covered Bridge
• Rocky Gorge Scenic Area (parking can be found at 44.0016667175862, -71.27716637107925)
• Sabbaday Falls
• Sugar Hill Scenic Overlook
• CL Graham Wangan Overlook
• Hancock Overlook (this one is right at the famous hairpin turn – can’t miss it!)
• Lincoln Woods Trailhead – Scenic suspension bridge over the river that’s not far from the parking lot.

🍁 Before hopping on The Kanc, consider downloading this great audio tour to enhance your drive – Click here to check out this audio tour!

There are also tons of hiking trails along The Kanc , so if you’re looking to squeeze in a hike on the drive, this is something to consider. But if you don’t have extra time, I would suggest moving on to Franconia Notch State Park, and only doing hikes along The Kanc if you’re able to add an extra day in.

After The Kanc, your next stop is Franconia Notch State Park . And this is where most of the top things to do are , especially in the fall season .

Flume Gorge is one thing I recommend you do if you can only pick one attraction. Flume Gorge is a very fun 2-mile loop trail that takes you over 2 covered bridges, and through the granite gorge. Along the trail, you’ll have some really gorgeous spots to admire the fall foliage, too.

Not sure if this is right for your itinerary? Click here to check out my detailed post in if Flume Gorge is worth visiting , and everything you need to know to plan the perfect visit.

Pro Tip: Buy your Flume Gorge ticket online in advance to save a few bucks! On weekends in the fall season, it’s also possible that certain time slots will sell out. This is another reason to book in advance.

If you have time to explore more of Franconia Notch State Park, I also recommend these activities:

• Cannon Mountain Aerial Tramway
• Artist Bluff Trail (famous spot that ends overlooking Echo Lake – amazing during foliage season!)
• The views at Echo Lake Beach

Where To Stay Near Franconia:

• Sugar Hill Inn – 15 mins from Franconia Notch Park, and is rated as the best B&B in New Hampshire!
• Riverwalk Resort – 5-7 mins from the top attractions in Franconia.
• Woodstock Inn & Brewery – Cozy inn with a brewery.

Here are some posts to help you plan this portion of your trip:

• Fun Things To Do In Franconia, NH
• Fun Things To Do In Littleton, NH
• Fun Things To Do In Lincoln, NH
• Where To Stay In New Hampshire In The Fall
• Where To Stay In The White Mountains: Guide To The Towns

Day 7 – Drive To Stowe Or Woodstock, VT

Begin your day in New Hampshire with a country breakfast at Polly’s Pancake Parlor! This place is famous in New England, and truly has some of the most amazing pancakes I’ve ever had. It does get busy in the fall season, but man, it’s so worth it.

Then, on to Vermont you go! For the next 2 nights, you’ll want to choose between Stowe and Woodstock, VT as your home base. These towns are the absolute best to visit in Vermont during a New England fall road trip because of foliage views and small-town charm. They’re only 1 hour and 15 minutes from each other, so, you can choose where you want to stay, and then visit the other as a day trip.

The drive to both Stowe and Woodstock is 1 hour and 30 minutes from Franconia , and since this is a shorter drive, you can make some stops along the way, or drive straight there. Stowe and Woodstock both have a lot to do, even though they’re small towns, so it’s beneficial to drive straight there and make sure you have plenty of time to explore.

If you choose to stay in Woodstock, I suggest stopping at the King Arthur Baking Company campus on your way because it’s pretty much on the direct route. It’s a really fun place with fresh baked goods and breads, a café, and a fun shop where you can stock up on pantry staples and baking mixes.

Do I recommend you stay in Stowe or Woodstock? I honestly love both equally! There’s no wrong choice here.

The biggest difference between the two is that Woodstock feels a bit more upscale, and Stowe definitely has a very casual feel to it. But the difference is minor. Both have charming covered bridges, great shops, amazing restaurants, a quaint town feel, and plenty of things to do.

Where To Stay In Stowe :

• The Green Mountain Inn . It’s located right on Main Street, so you can walk to a lot of places.
• Spruce Peak Resort . Perfect for those wanting a resort feel, and it’s right off the scenic Smugglers Notch drive. There are rooms with gorgeous mountain views here, too.

Where To Stay In Woodstock :

• The Woodstock Inn & Resort . It’s referred to as Vermont’s most beautiful address, and it’s in the heart of Woodstock’s village. This is a luxury hotel that’s worth it!
• 506 Inn On The River . Located just outside of the village, this is a modern and cozy inn, well … right on the river 😉

Here are some posts that will help you plan your time in Stowe and Woodstock:

• Best Things To Do In Stowe
• Best Things To Do In Woodstock

Day 8 – Explore Stowe & Woodstock, VT

Depending on where you stay, you’ll want to take a day trip to the other town this day. Below are breakdowns of the can’t miss things to do in each town .

Best Things To Do In Stowe :

• Explore the cute shops along Main Street (don’t skip the Stowe Mercantile!)
• Drive Smugglers Notch for amazing foliage.
• Ride the gondola to the top of Mount Mansfield, the highest peak in Vermont (this is epic during the fall season!). This is located at the midway point along the Smugglers Notch drive.
• Visit Emily’s Covered Bridge, and learn about it’s spooky history.
• Sample the hard cider at Stowe Cider.
• Sip on craft brews at Alchemist Brewing (one of my favorites in New England).

Best Things To Do In Woodstock:

• Stroll through the charming downtown shops and eateries.
• Pop into Mon Vert Café for a warm drink.
• Snap a photo with Middle Covered Bridge in town.
• Drive over Taftsville Covered Bridge to visit Sugarbush Farms. You’ll be able to sample homemade cheese and fresh maple syrup here, and also take in amazing foliage views.
• Visit Billings Farm & Museum.
• Drive over to Sleepy Hollow Farm to see the famous farm landscape spot.

Day 9 – Drive To The Berkshires Or Litchfield, CT

Next up – The Berkshires or Connecticut! This choice is yours entirely. Let’s start with the option to drive to The Berkshires.

The Berkshires is an iconic region in Massachusetts that’s a really great one to visit for fall foliage. Here, you’ll find cute towns, loads of fall color, lots of scenic hikes and walks, and awesome dining options.

Depending on which town in Vermont you’re coming from, the northern region of The Berkshires area will be just over 2 hours from Woodstock, or just over 3 hours from Stowe .

The drive from either town to The Berkshires will pass through Rockingham, VT, and you’ll definitely want to stop here to visit the Vermont Country Store! There’s also the very cute Kissing Covered Bridge here that makes for a fun photo.

Once you arrive in The Berkshires, I suggest you start in Williamstown, and drive the scenic Route 7 down to Sheffield. This drive without stops takes about 1 hour and 15 minutes, but I would budget at least a few hours to make stops and enjoy some other fun activities. This route packs a lot into a perfect fall day, without a lot of driving.

During this drive, these are the best stops to make:

• The Mount Greylock Auto Road to the highest peak in Massachusetts (absolutely amazing in the fall season!).
• Make a detour off Route 7 to Bartlett’s Orchard in Richmond for the perfect fall farm experience.
• Continue with your short detour to Hilltop Orchards, which is 5 minutes from Bartlett’s, and where you can sip on artisanal craft ciders!
• Walk through the charming town of Lenox.
• Stroll through quaint Stockbridge, too!
• Snap photos with the covered bridge in Sheffield.

Where To Stay In The Berkshires:

• The Red Lion Inn . A historic and famous inn in the heart of Stockbridge.
• The Dewey . A cozy, traditional New England B&B in Lenox.

The other option is to drive to Litchfield, CT , which is south of The Berkshires. It’s a longer drive from Vermont, but you could also turn this into a fun road trip day by driving the same Route 7 itinerary as mentioned above through The Berkshires, and then continue on to the Litchfield Hills. I would probably only choose this option if you wanted to take your time exploring the awesome stops along Route 7 in The Berkshires, arrive in CT in the evening, and then explore this region of CT the next morning before your drive back to Boston.

How To Spend Your Time In Litchfield Hill, CT:

Since you’re likely coming down through the western border of Massachusetts, I would start in Kent, and work your way east. You probably won’t have time to do everything on this list, but pick and choose based on your preferences and schedule.

• Explore the cute town of Kent, and then visit Kent Falls State Park if you have time.
• Continue to follow Route 7 to New Milford. The drive is very scenic!
• Stop in New Milford to enjoy the quaint town, and then visit Lover’s Leap Bridge.
• Head over to Washington, and then continue on to Mount Tom State Park for awesome foliage.
• End in the charming town of Litchfield.

Where To Stay In The Litchfield Hills : Litchfield Inn . Refined and still very cozy, and one of the best in the area!

Should I do The Berkshires or Litchfield, CT? Personally, I would stay stick to The Berkshires since this will allow you a more relaxed itinerary. There’s so much to do, and plenty of foliage scenery to take in. If you do the Route 7 drive quicker than you were anticipating, you could always shoot down to the Litchfield Hills for an impromptu adventure 🙂

I would choose to add on the Litchfield Hills if you’re feeling adventurous, and really want to see as much of New England as possible.

Day 10 – Drive Back To Boston, Stopping In Sturbridge or Litchfield On The Way

If you have time to explore another cute town on your drive back to Boston, I would suggest either tacking on a quick drive through the Litchfield Hills, CT if you didn’t already, or a stop in Sturbridge, MA. Sturbridge is more on the way to Boston, and offers beautiful foliage.

How to spend your time in Sturbridge, MA :

• Visit Old Sturbridge Village for all the cozy fall New England vibes (this is a must if you have time!).
• Pop into Saw Dust Coffee & Dessert Bar for lunch and treats.
• Sip on craft beer at Altruist Brewing Company.

And of course, as mentioned in the previous day’s itinerary, the Litchfield Hills region has plenty to offer for foliage views, small towns, and beautiful scenery.

But, if you have a flight to catch, then don’t risk it, and head straight to the airport! 🙂

Optional Adjustments For The 10 Day Itinerary:

• You can easily cut out Acadia National Park, and head straight to New Hampshire, and choose to spend more time there. Acadia is out of the way, and further north, so I know it doesn’t suit everyone’s plans. This would allow you time to definitely ride The Cog, and have a more relaxed schedule.
• If you would rather have more time in Vermont, you can skip The Berkshires/CT. This is personal preference! Both areas are amazing for fall foliage, but nothing is quite like Vermont in the fall. This would allow you time to move at a slower pace. If you decide to skip The Berkshires/CT and stay in Vermont for a third night, see my 12 day itinerary, option 3 for suggestions on what to do!

12 Day Road Trip Itinerary Option

If you have 12 days (or more!), this is truly awesome. I would follow my 10 day itinerary, and then take one of these suggestions:

Option 1 : Add in 1 day to see Litchfield, CT after The Berkshires . Since you have the extra time, you can definitely see the Litchfield Hills region of Connecticut with this itinerary! I would recommend this option for those who really want to see as much of New England as possible, and make all the rounds.

Option 2 : Add an extra day to Littleton/Franconia. This region has so many great hikes and places to spot fall foliage. It’s well worth adding a day to this part of the trip if you have the extra time. This would allow you a half day to ride The Cog, and takes more scenic walks and hikes to enjoy the fall foliage.

Option 3 : Add an extra day to Vermont. On your extra day, you can take a day trip to Burlington and Shelburne, or spend the day driving the back roads .

Burlington & Shelburne, Vermont things to check out :

• First, the drive from both Stowe and Woodstock to Burlington on I-89 is beautiful in the fall. You’ll see lots of mountains ablaze with fall color.
• In Burlington, check out the waterfront area, and walk along Lake Champlain.
• Burlington also has an awesome craft brewery scene, and Foam Brewers is especially great.
• The American Flatbread restaurant in Burlington is a cozy place to stop for lunch.
• Church Street Marketplace in Burlington is a must!
• In Shelburne, you’ll want to spend most of your time walking around Shelburne Farms. This is a historic farm once owned by the Vanderbilt family, and has beautiful hiking trails, and you can also sample their homemade cheeses. Definitely do the Farm Trail, which takes you to an epic view of Lake Champlain.

Vermont back roads driving itinerary near Stowe :

This drive is easier to do from Stowe, but it’s also doable from Woodstock if you’re okay with a longer day. This itinerary is is order based on departing from Stowe, but you can also adjust based on which town you’re coming from 🙂

• The covered bridges in Montgomery, including Montgomery covered bridge (which is actually in Waterville), and Longley Covered Bridge.
• Barn Owl Bistro is a hidden gem nearby that’s a great little pitstop.
• The town of Cabot and the nearby AM Foster Covered Bridge are really beautiful areas to visit full of rustic Vermont charm.
• Peacham is a very small town with iconic landscapes and scenery.
• Bogie Farm in East Ryegate is a landscape that worthy of a postcard, and is especially beautiful in the fall.
• The drive between all these destinations will also be lovely and scenic, and packed with fall color.

1 Week (7 Day) New England Fall Road Trip Itinerary

If you have 7 days, welcome to your itinerary! This option is the same as the 10 day option, but eliminates Acadia National Park to save time.

7 Day Road Trip Overview

Day 1 : Arrival In Boston Day 2 : Drive To Jackson, NH + A Stop In Salem, MA Day 3 : Drive To Franconia Along The Kancamagus Highway Days 4-5 : Drive To Stowe or Woodstock, VT + Stay 2 Nights Day 6 : The Berkshires Day 7 : Return To Boston

For this itinerary, you can also eliminate The Berkshires, and stay an extra night in Jackson or Franconia.

5 Day New England Fall Road Trip Itinerary

With 5 days, you can go in a few different directions, and below, I break down my suggested options, and the benefits of each. This way, you can tailor it to your preferences.

Option 1 : Spend two nights in Boston with a day trip to Salem, then spend 3 nights in Stowe/Woodstock, VT.

Option 1 is perfect if you prefer staying in one place longer. This itinerary will allow you to stay in the same hotel in Boston for 2 nights, and take an easy day trip to Salem for the perfect fall day of Halloween fun and history! Then you can pick up your rental car (if you haven’t already), and drive to Stowe or Woodstock, VT for 3 days to explore both towns.

With 3 days in Vermont, you can easily see both Stowe and Woodstock, and maybe even plan a day of driving around the back roads. See the 12-day itinerary option for my suggestions on driving the back roads around Vermont during foliage season .

Option 2 : Spend 1 night in Boston, stop in Salem on your way to Franconia and spend 2 nights in Franconia. Then spend 2 nights in Stowe/Woodstock, VT, and then drive back to Boston.

Option 2 is perfect for those who still want to see as much as possible in 5 days. You’ll get to see a bit of New Hampshire and Vermont, while making a stop in Salem.

Note: For this itinerary, I would drive from Salem to Conway, and the drive The Kancamagus Highway on your way to Franconia so you get to experience the fall foliage along this route. But this itinerary option eliminates the stay in Jackson, as there are more fall things to do in Franconia.

Option 3 : Spend 1 night in Boston, 1 night in Salem, 3 nights in Stowe/Woodstock, VT, and then back to Boston.

Option 3 is perfect for those who really want to spend some time in Salem. This itinerary allows you to spend a whole night in Salem to really enjoy all the Halloween festivities and tours, and then you can spend 3 beautiful days in Vermont.

I excluded New Hampshire from this option because I felt like it would be too much to cram in when adding 1 night in Salem. But if you were feeling adventurous (I’ve been there, I get it! 😂), you can drive to Franconia, NH for 1 night after Salem, and then do 2 nights in Vermont instead of 3.

3 Day New England Fall Road Trip Itinerary

3 days in New England is the perfect long weekend getaway!

With 3 days, I suggest you stay in one location , and add day trips . If you’re flying into Boston, you can stay 1 night in Boston if needed, and then drive to Vermont or New Hampshire for 2 nights. If you’re not flying in, you can spend all 3 nights in Vermont or New Hampshire.

Stowe is very close to New Hampshire, and it’s only about 1.5 hours from Franconia. You can easily do a day trip from Stowe to New Hampshire, or vice versa, for this type of itinerary.

It would also be easy to work in a stop in Salem, MA, either on your way in or out of Boston.

Weekend New England Fall Road Trip Itinerary

For a weekend getaway in New England (essentially, 2 days), I would also recommend you stay in one place and take a day trip. For this itinerary, I almost always suggest Stowe or Woodstock. You can stay in either town, and spend 1 day exploring that town, and then the next day, exploring the other as a day trip.

Vermont Fall Road Trip Itinerary

Looking to just see Vermont? Excellent choice. It’s my personal favorite fall destination in New England (even though it’s a very close call 😉)

For a Vermont fall road trip , you can really do it in anywhere from 5-7 days. Of course, more is better to really see everything, but generally speaking, you can actually make it happen in a week or less. A popular route to take in Vermont is Route 100 , which runs the entire length of state, right through the middle. This allows you opportunities to veer off and see some other places as well.

For the purpose of this itinerary, I’m going to provide a week-long (7 day) itinerary, and you can adjust it to your own plans.

Day 1 : Bennington & Manchester Day 2 : Drive to Woodstock, stopping in Grafton and Weston on the way Day 3 : Spend the day in Woodstock Day 4 : Drive to Stowe, stopping in Montpelier if you’d like Day 5 : Spend the day in Stowe Day 6 : Staying in Stowe, take a day trip to Burlington & Shelburne Day 7 : Drive back

Day 1 Suggestions : Bennington and Manchester are pretty close to each other, so you can easily do both in one afternoon. There are some wonderful covered bridges in the area to see, and here are some more things to check out:

• The Bennington Battle Monument for fall foliage scenery.
• Downtown Bennington for shopping on Main Street (small, but cute!).
• Apple Barn is a few minutes from Main Street for a fun country store and bakery.
• Zoe’s in Manchester for lunch (great sandwiches!)
• Downtown Manchester for shopping in a cute town (don’t skip Northshire!)

Day 2 Suggestions : Grafton is a very small town, but it’s quintessential Vermont. It has a cute little cheese shop, and a nice little market/cafe called MKT Grafton, which is perfect for a quick bite. Also, swing by Weston to visit the Vermont Country Store.

For the rest of the itinerary, refer to the 10 day option for details 🙂

Click here to check out my post on a Vermont covered bridges road trip!

New Hampshire Fall Road Trip Itinerary

My second favorite fall foliage destination! Here’s my suggested itinerary for a New Hampshire-only fall road trip.

To just see New Hampshire , you can also spend anywhere from 4-7 days.

With 4 days, you can easily just stick to the White Mountains region, but I’m here to give you all my tips on even more awesome places to see in the fall season in New Hampshire ☺️ So, this itinerary will be 7 full days , but adjust as you need to!

Day 1 : Portsmouth Day 2 : Lake Winnipesaukee Days 3-4 : Littleton/Franconia Days 5-6 : North Conway/Jackson Day 7 : Drive back

Connecticut Fall Road Trip Itinerary Option

If you’ve seen all the “hot spots” around Vermont, New Hampshire, Massachusetts, and Maine, and you’re looking to explore a new part of New England in the fall, Connecticut should be next on your list!

As mentioned, my favorite place in Connecticut for fall foliage is the Litchfield Hills region. I always like to share that this region was what inspired Amy Sherman-Palladino’s creation of Stars Hollow, so Gilmore Girls fans will especially love this area.

The Litchfield Hills is very compact, and you can easily do a lot in a weekend here. However, 3-4 nights will allow you a nice, leisurely pace to explore all the amazing things this region has to offer in the fall.

The best towns to stay in in the Litchfield Hills region are:

• New Milford
• Washington/Washington Depot

Of all these towns, Litchfield probably has the most options when it comes to shopping and dining, however, they’re all very quaint and charming. I would pick whichever one has the best hotel for your plans.

If you have extra time for your Connecticut fall road trip, you can tack on places like Canaan to the north of the Litchfield Hills region, drive to Glastonbury, and then through the River Valley region, which includes the adorable towns of Chester and Essex. You can also choose to end your road trip in Mystic.

What To Pack For A New England Fall Road Trip

I always start every New England packing guide with the same thing, and this post is no different: begin to check the weather reports 5 days out from your trip to get an idea of what the weather will be like . And keep checking it until the day before you leave .

This is because weather in New England can change quickly, especially in the fall season. It’s not quite as dramatic as say … Iceland 😉 But, it can change and vary a bit. Generally speaking, fall will be chilly and a bit rainy. However, you could also have warm and sunny days. For longer trips, you’ll want to pack for both scenarios.

Here are some things I recommend you consider when packing for a fall road trip through New England:

Waterproof hiking boots . If you plan to do any hiking, or even nature walks, you’ll want a pair of sturdy boots that are waterproof. Even some attractions like Flume Gorge and other waterfalls in New Hampshire are pretty wet, so this is a good idea to stay dry and comfortable. I really like the Eddie Bauer K-6 Hiking boots. Find the women’s version here and the men’s version here . They’re a much less expensive version of the famous Danner hiking boots featured in the movie Wild !

Good hiking socks to keep your feet dry . An awesome brand to support is Tarn Tough Socks , which is a Vermont-based company. They’re an investment, but they’re also the best, and come with a lifetime guarantee!

Waterproof rain jacket to stay dry if it rains . You won’t want to let the rain slow you down, especially if there’s a lot in the forecast! So definitely pack one that’s completely water proof ( not water-resistant).

Layers . The best way to dress in the fall season is with layers. Under your rain gear, flannels, sweaters, and lightweight t-shirts (both short-sleeved or long-sleeved) work great.

Jeans . These work really well for most days. Fall in New England is pretty casual.

Hiking clothing . For any hikes you want to do, pack whatever clothes you typically wear and feel comfortable in 🙂

Comfortable sneakers or boots . When it’s not raining, a good pair of comfortable sneakers or cute boots work perfectly, depending on your plans. Since I drive from New York, I don’t usually have to worry too much about weight limits on a suitcase, so I’ll throw a pair of sneakers, flat boots/booties, and my hiking boots into the car. This is usually all I ever need.

Dinner outfits . New England is home to incredible places for farm-to-table dining, some of which are a bit more fancy. If you plan to go out for a nice dinner or two, you’ll want to pack accordingly. New England isn’t super fancy, so women can do a casual dress/jeans and a nice top with booties in the fall, and men can easily do dark-wash jeans and a button down top.

Reusable water bottle . You’ll need to stay hydrated while out exploring!

Day pack . If you plan to do any hiking, you’ll want to bring a day pack with you to carry your essentials. If you don’t plan to do any hikes, you can probably skip this, as you can keep most everything you need in your car or room.

Does It Snow In New England In The Fall?

Here’s the thing – it might if you’re up in the mountains. However, it doesn’t usually snow during peak foliage times. Usually, New England gets its first snow of the year later in October or early November. So, I wouldn’t worry about packing any snow gear or winter boots for your fall road trip.

How Do To A New England Fall Trip On A Budget

So, first thing’s first, you’ll unfortunately have to rethink what “budget” means in New England, especially during peak season in the fall. It’s generally more expensive than other areas of the country regardless of the reason, so during prime foliage times, prices will go up significantly.

Especially in the past, I never had the money to spend on several nights at hotels during this time of the year, so I have learned to do it on more of a budget. Not necessarily cheap, but not as tough on the wallet 😉 Here are my tips:

• Stay in motels. I love a good hotel splurge, and do it more now than I did in my 20s and early 30s. But for most of my road trips when the focus in exploring outdoors, I stay in motels with efficiency kitchens . You can find some really nice ones, and while they’re likely to be outdated, they’re usually clean and cozy.
• Efficiency kitchens allow you to make some meals at home. For a road trip style trip, this may be more challenging, as it’s hard to bring perishable items with you to store in a fridge. But I usually try to make my own breakfasts to save money, and pack snacks to have for lunch.
• Stay outside of town. If you’re really on a tight budget, you can stay outside of the towns you’re visiting. Places like Franconia, Stowe, and Woodstock charge premium rates for peak season, so you’re likely to find deals a town or two away.
• Go camping! If you’re really adventurous, you can go camping! There are camp sites all over New England, and this will definitely be more affordable. One thing to keep in mind is the colder weather, and for this reason, some camp sites may close down after Indigenous People’s weekend in October. But many remain open, and offer Yurt-style camping, too.

Is Fall In New England Worth It?

A resounding yes! I truly believe this is such a magical time to visit – if not the most magical time. Despite the crowds and the cost, it’s more than worth it. Many of the landscapes you’ll see are actual stock photos and postcards, and since so many people equate the fall season to all things cozy, there’s really no cozier place to be than in New England during foliage season.

More posts you may enjoy:

• Fall In New England: The Best Things To See & Do
• Vermont In The Fall: Festive Things To Do!
• Fall In New Hampshire: The Best Things To Do
• Fall In Massachusetts Ultimate Guide: All The Best Things To Do & Foliage Spots!
• The Best 7 Day New England Road Trip Itinerary For Any Season
• Best Stops To Make On A Boston To Stowe, VT Road Trip
• Vermont vs. New Hampshire In The Fall
• Maine In October: Best Towns For Foliage & Things To Do!
• Best Vermont Pumpkin Patches & Farm Stands To Visit In The Fall
• Awesome Corn Mazes In Vermont
• Best Time To Visit New England
• Best Time To Visit Vermont

That’s A Wrap On The Best New England Fall Road Trip Itinerary

And there you have it! All my tips and expert advice on planning the most epic New England fall road trip during foliage season! This truly is such a wonderful, once-in-a-lifetime experience that everyone should do at least once, and hopefully, you’re now well on your way to planning your own foliage adventure through New England!

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• Connecticut fall getaways

Fall in Connecticut: Everything You Need to Know

• July 13, 2023

Little, overlooked Connecticut is a state of many firsts.

Connecticut was the first state to institute speed limits for drivers. It did so in 1901, declaring that going over 12 miles per hour was speeding.

If Connecticut had kept that law in place, perhaps it would not be seen as just a drive-through state for travelers between New York and Boston. Or maybe those travelers would just malign Connecticut more than they do now.

But if they stopped and had a look around, maybe they’d understand better why locals love Connecticut so much—especially during the fall season.

Our little state has the longest fall foliage season, in fact.

Granted, travelers can still enjoy the visual splendor of Connecticut fall foliage from the highways. Still, there’s so much more to experience when it comes to fall in Connecticut.

Read on for our guide to getting the full fall experience in Connecticut.

Your Bucket List of Things to do in Connecticut in the Fall

Maybe it’s the shows on TV or movies on the big screen, including:

• “Gilmore Girls”
• “Firestarter”
• And “the Haunting in Connecticut”

But people seem to most often equate Connecticut with autumn.

For good reason, it, like many other New England states, truly shines during those few months between  summer  and winter.

Sometimes, it’s helpful to have a list in front of you to keep track of all that there is to see and do. So without further ado, here are some things to keep an eye out for in Connecticut this fall.

Connecticut Fall Foliage

Connecticut boasts the longest season for fall foliage in all New England states.

While every year is different,  Connecticut’s fall foliage  is most vibrant from early October to very early November. The Connecticut Forestry Department and state foresters refer to that period as “peak foliage” in their foliage report. Some years, we can enjoy the foliage well into November, but that’s an anomaly.

CONNECTICUT FALL FOLIAGE DRIVES

Driving along scenic roads is the most obvious pick for seeing CT’s fall foliage for yourself.

While the speed limits are much higher than in 1901, don’t go too fast, or you might miss the best parts of leaf peeping.

Some of the top picks for  Connecticut fall foliage scenic driving routes  include points from each of the corners of the state:

• Merritt Parkway
• Driving from Greenwich into the  Litchfield Hills
• Round Hill Road, North Street, and Lake Avenue in Greenwich, CT
• The Shoreline drive to Essex, CT

Essex, CT, Fall Foliage

That last option for scenic driving, to the stretch of CT shoreline towns from Guilford to Essex, is a longer trek. However, it’s worth the trip, as this fall foliage destination offers one of the  most unique Connecticut experiences  in the state.

Essex Steam Train  leaves from the historic Essex, CT, train station. From there, it pulls its vintage coaches along the Connecticut River Valley on a 12-mile round trip stretch of old train track.

If an old-fashioned riverboat is more your thing, the Becky Thatcher riverboat leaves from the landing at Deep River. It then takes you for an hour-and-a-half journey along the fall colors of the Connecticut River Valley.

While these Essex, CT, attractions run throughout the year, fall foliage season is among the most spectacular times to take a ride.

Connecticut Fall Foliage Day Trips

Speaking of the Essex Steam Train, there is more to experiencing the fall than simply driving around.

The third smallest state in the Union, no town in Connecticut is far from anywhere else in the state. The longest drive, along the Connecticut shoreline, takes less than 2 hours.

Still, I encourage you to take way longer than that, so you can stop and explore some of the best fall towns on your  Connecticut day trips

Best Connecticut Towns in the Fall

Pretty much any town in Connecticut has something appealing about it in the autumn.

Nevertheless, Connecticut has 169 towns, so we all have to prioritize.

You may be surprised to learn that this Greenwich native is not including Greenwich on the list of Connecticut towns to visit.

Greenwich is beautiful any time of year, and there are plenty of things to do year-round. That said, the towns on this list are built around the Fall.

Moreover, all of them, Greenwich included, made our list of the  best cute towns in Connecticut

Connecticut’s number one tourist attraction is a prime destination for visitors looking to experience the fall.

Many of the  best attractions, activities, and things to do in Mystic, Connecticut , are best enjoyed in the fall. And any time of year is a good time for ice cream at one of the various shops in downtown Mystic.

Mystic Seaport looks straight out of a magazine in the fall, with historic buildings draped in fall color. The blue water of Mystic River perfectly contrasts the explosion of color on the surrounding shores.

Visit the local farms for fall goodies, and check-out BF Clyde’s cider mill. It’s the last steam-powered one in America and was designated a National Mechanical Engineering Landmark in 1994. Even if you’re not into historic mechanical marvels, the cider slushies and cider donuts are delicious.

Litchfield County Hill Towns

There are many towns in this part of the state.

They’re all so small, though, that an afternoon would be enough to knock most of them off your list without too much struggle. And the Litchfield Hills is famous for its fabulous fall foliage.

But if you’d rather spend more of the day in any given town, head to one of the many nearby  CT state parks

• Cornwall features one of the historic covered bridges that screams New England in the fall.
• Kent has Kent Falls State Park, Bulls Bridge, and an artsy community that’s become a big draw for New Yorkers with cars.
• New Milford has the cutest town green and quaint downtown. I’d be shocked if it hasn’t been featured in movies.
• The drive between New Preston and Bantam has a hike up Mount Tom State Park
• Nearby Simsbury, CT , is another cute town, with the Heublein Tower overlooking it from the top of Talcott Mountain State Park

Most of these are close to if not following the Housatonic River and Route 7. This northwestern corner of the Nutmeg state is also where you’ll find the our piece of the Appalachian Trail, if you’re particularly adventurous.

Connecticut River Valley

One of the last great wild places according to National Geographic, this river valley is another fall destination. Especially the portion from Middletown, CT , down to Long Island Sound. Festooned with beautiful fall foliage, the valley looks gorgeous from Gillette Castle State Park. Or traipse through Devil’s Hopyard State Park on a possibly spooky hike to Chapman Falls.

Activities for Fall in CT

Sure, walking around the downtown of a cute Connecticut fall town can be fun, but what about things to do?

If you’re the type that wants to do a quick photo shoot, pumpkin in hand, for Instagram, or more interested in disconnecting and getting lost in the fall woods, Connecticut in the fall has you covered.

Be sure to read our complete  guide to fall activities in CT , but here are some ideas as a primer:

Fall Foliage Hikes

Almost anywhere in the state has fantastic hiking trails through state parks and state forests to see fall foliage.

Of all the  Connecticut hiking trails , though, one of the rewards of the more intense hike, with one of the most splendid fall views in Connecticut.

Heublein Tower, perched on a ridge in Talcott Mountain State Park, requires a steep hike. But once you get there, the tower offers a 360-degree view of the surrounding Farmington River Valley  Hartford  and the surrounding towns are within sight, plus the surrounding hills and valleys, swathed in golds, reds, and oranges.

Mohawk State Forest, straddling Goshen, Cornwall, and the town of Litchfield, CT ; offers plenty of views over its rolling hills, as well. And Pachaug State Forest, at the other extreme of the state, offers 27,000 acres-worth of opportunities to get lost in peak fall foliage.

Head to Hamden, just north of New Haven, to find Sleeping Giant State Park. As the name implies, the mountain looks like a giant taking a nap. And the lookout tower has a sweeping view of the surrounding area. Add a trip on your bike or two feet along the nearby Farmington Canal Heritage Trail. It passes the foot of the mountain on its trek from New Haven, CT , towards the town of Farmington, Connecticut , and onwards to the Massachusetts border.

For something less strenuous, head to the Connecticut shoreline. Hammonasset Beach State Park may not be full of colorful fall foliage, but its an interesting mix of shoreline pines and salt marshes.

Farm Visits During Fall in CT

Connecticut only recently switched from rural to suburban, a fact downtown Greenwich and Stamford hide well. Like much of the country, Greenwich made the switch only in the last few decades.

Still, large stretches of the state that magically rural, with farms that work here being prime places to visit in the fall.

September  and October are perfect months to go  apple picking in the various Connecticut apple orchards , for example.

Many farms also stretch the season-out by offering:  cider mills , pumpkin picking , and  Connecticut corn mazes .

So shop local at a Connecticut farm market, or peruse a corn maze or two. And don’t forget to stock up on a bag of apple cider doughnuts at one of the CT cider mills before, during, or after your visit to one of the best places to see fall foliage near NYC .

Haunted Connecticut

There’s a reason people associate Connecticut with hauntings. It’s one of the oldest states in the Union, with plenty of opportunities to acquire a spirit or two with unfinished business.

While many of the most haunted houses are privately owned, there are still some fun haunted houses for Halloween. Try to snap a picture of the ghosts at the  Lockwood-Mathews Mansion Museum . You can also head to Mill Hill Historic Park for a lantern-lit walk through the graveyard.

Haunted Houses

A haunted house can be a fun way to give yourself a little scare.

The best haunted houses near Greenwich are in nearby Westchester County .

Find a Haunted Place in Connecticut

If you’d rather something a little less structured, you can check out some of the most-haunted places in Connecticut :

• Bruce Museum in Greenwich
• Union Cemetery in Easton
• Dudley Town (careful, this is private property)

Explore the Stomping Grounds of the Headless Horseman

These two Hudson River Valley towns cash in each year on their most famous undead resident with all sorts of Halloween events.

And that cash cow now settles throughout the Lower Hudson River Valley in the fall. The Great Jack O’Lantern Blaze at Van Cortlandt Manor in the town of Croton-on-Hudson, New York is steadily gaining popularity. And with over 7,000 hand-carved, illuminated pumpkins and fall-themed treats on display at this spectacular event, it’s easy to see why.

Fall Festivals in Connecticut

While Sleepy Hollow’s events are well-known, plenty more fall festivals are in our state. Click the link to see our complete list of fall festivals and events in Connecticut .

Fall Beer and Wine Tastings

pkin and apple picking or exploring corn mazes, there are still more farms to check-out.

In this case, Connecticut has a growing vineyard and winery industry scattered throughout the state. Read our guide to the  best wineries on the CT wine trail  for a full trip.

I’m personally more partial to the beer brewed in Connecticut than the wine. But to each their own.

We’ve got a list of the  best breweries in Connecticut and Westchester County  if an autumnal day of sampling local brews is more your style.

And CT cider mills have been churning out the hard stuff for centuries. Even if it’s only recently become popular again.

Fall Antiquing in Connecticut

The  Greenwich Avenue shopping district  is always a top destination.

To top it off, fall just seems like the perfect time to go antiquing through New England for some reason.

Be sure to visit the Main Street of Woodbury to explore the Antique Capital of Connecticut.

Comb through the Connecticut antiques trail’s  list of antique stores in CT  and pick a few along your planned day trip route. I also highly recommend the  Elephant’s Trunk flea market  in New Milford on a Sunday morning in the fall.

In this writer’s opinion, fall is the best time to explore the  top Connecticut flea markets .

November in Connecticut

However, the fact that everyone does these things means that other months have their own pleasures.

In the case of November in Connecticut , fall foliage extends into the beginning of the month. And with fewer people, you often have entire attractions to yourself.

What About Connecticut in the Winter?

Fall is synonymous with New England and Connecticut. And yet, winter in Connecticut has its own special features that you can only appreciate when you’re here.

There are plenty of romantic things to do in CT during the winter months .

Be sure to check out our guides to:

• Winter activities in Connecticut
• The best places to visit in Connecticut for winter vacation getaways
• The best things to do in Connecticut in December

Read up on our guide to planning a romantic winter weekend getaway in Greenwich, CT , if you’d like the planning done for you.

Keep Planning Your Fall in CT Getaway

Are you still not convinced that you have to experience fall in CT?

Then keep exploring our getaway guides, good for any time of year:

• The best weekend getaways from Boston
• Top picks for road trips from New York City

And keep exploring the many things to do in Greenwich, CT, and nearby when you check out our free visitor’s guide to Greenwich .

Updated and republished: July 13, 2023

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21 Small Towns in Connecticut You Might Fall in Love With (2023)

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Nowhere else in America has as many cute little towns as New England. Of all the states,  you’ll find some of the cutest small towns in the tiny state of Connecticut ! In many of these spots, you’ll find historic sites and local charm that perfectly represents that New England aesthetic. 

From cute coastal beach towns to  quaint historical villages, I’ll give you the inside scoop on the cutest small towns in Connecticut that you’ll love visiting.

Table of Contents

Small Towns in Connecticut

A mention of Essex  CT, is the only way to start a list of the cutest small towns in CT. You’ll soon realize why it was voted one of the “best small towns in America.” The small-town charm captivates all who visit to experience a historic riverside town.

Essex is located in Middlesex County, right on the Connecticut River. The river played a huge role in developing the town. It’s famous for shipbuilding that you can learn more about in the Connecticut River Museum . The museum holds maritime exhibitions, shipbuilding artifacts, and, of course, gorgeous views of the river.

One of the best ways to take in the sights of the cute town is by cruise. The Essex Steam Train and Riverboat  provides leisure cruises in the Connecticut River on a historic riverboat. What a way to connect with the town’s past!

After spending time on the waterfront, head downtown and go for a stroll on Main Street. You’ll find lots of cute boutique shops and restaurants established in historic, federal-style buildings. Make sure to visit Truffle Shots , you’ll find some of the best chocolate in the entire state.

And if you’re looking for a place to stay in Essex, consider a stay at the Griswold Inn ! It’s one of the oldest continuously operated inns in the country and its absolutely adorable.

Click Here to Check Prices & Book

A quite quaint beachtown in Connecticut, Niantic has so much charm!! You’ve got the lovely downtown area with its variety of boutique shops and restaurants, perfect for taking a stroll and window shopping. Do you like vintage shops where you can find unique and interesting one of a kind items? Anna Pearl’s Curiosities is one of the best antique stores in the state , and its got an eclectic selection of vintage clothing, antique jewelry, and memorabilia of all kinds.

Need a little sweet treat pick me up? Head to Sift Bake Shop , where you’ll find sweet and savory goodies that are sure to delight, plus coffee, tea, and local spirits, too!

Niantic is home to some of the most beautiful beaches in CT, and the waterfront views should not be missed. Rocky Neck State Park and Hole-in-the-Wall Beach are two of the most popular swimming spots, so if you’re planning a summer Connecticut trip, pack your bathing suit! For a scenic beach walk, be sure to check out the Niantic Bay Boardwalk, any time of year.

Looking for a place to stay in this cute CT town? Book a room at The Inn at Harbor Hill , a boutique property with waterfront views.

Click Here to Check Prices & Book!

A winner of Connecticut’s “Best Small Town” by Connecticut Magazine multiple years in a row, Norfolk is an easy addition to this list. This picturesque town is a popular spot for fall foliage seekers in the state, and it’s no wonder. You’ve got great gorgeous natural scenery and lots of great opportunity to get out in it!

Campbell Falls State Park is home to some of the best waterfalls in the state, and it’s a popular fall hiking spot. Haystack Mountain State Park is ideal if you’re looking for those birds eye scenic views. Plus, you can drive up Haystack if you’re not up for or able to make the hike, so it’s more accessible to all.

Norfolk is home to the Infinity Music Hall & Bistro , one of the top spots in the area for an evening out. The restaurant and live performances in an intimate space means there’s not a single bad seat in the house!

Wondering if there are any good places to stay in Norfolk? The Manor House Inn is almost as idyllic as Norfolk is.

  Many people consider Kent to be an escape from the big city. With just a short train ride from New York City, the bustling metropolis views will quickly transform into lavish natural scenery. The cute town of Kent not only has visual appeal but there are plenty of fun things to do around town.

Kent is located right along the Connecticut – New York border. It gives a huge contrast to the big city because it’s known for its vast natural landscapes surrounding it. Kent Falls State Park is one of the most popular attractions for people visiting the town. The park is home to 17 waterfalls , including the largest in the state. It’s a fun outdoor destination for hiking and sightseeing.

Just like the other Connecticut villages and towns on this list, there are plenty of landmarks in Kent that you don’t want to miss. Have your camera ready as you approach Bull’s Bridge, one of three remaining covered bridges in Connecticut. If you’re a literary fan, you’ll have lots of great reading options in the House of Books and Kent Memorial Library.

Immerse yourself into the friendly community by stopping by the Kent Farmers Market to chat with the locals and shop for fresh produce.

Interested in staying the night in Kent? Check out this gorgeous property with a fire pit near Lake Waramaug !

One of the most darling beach towns in the Constitution State, Westport is a picture perfect CT destination. There are three public town beaches, and Compo Beach is highly regarded as one of the prettiest beaches in the state. The boardwalk is the perfect spot for a coastal walk!

Also in Westport is Sherwood Island State Park , with over 235 acres of scenic beauty to explore. It’s also Connecticut’s first state park, and it’s a popular spot for swimming and picnicking in the summer.

Check out this two-hour Sunset Kayak Tour that would be the perfect cap to the day!

When it comes to where to lay your head at night, consider the lovely Inn at Longshore . You’ve got an onsite restaurant, pool, and you’re within walking distance of the beach – what’s there not to love?

One thing you’ve got to love about Connecticut is it’s cute coastal towns, and New London is one of them. New London has something that’s not so common in Connecticut, however, and that is a beach with soft, white sugar sand!

That’s right, if you’re looking for a place you can put toes in the sand, Ocean Beach Park is perfect. In addition to the beach, you’ll also find a boardwalk with arcade games, restaurants, gift shops, and even an Olympic sized pool! This is a very popular CT town to visit in the summer.

Would you like to stay in your own cozy rental with a fireplace, ocean views, and your own private beac h? Of course, who wouldn’t!

If the name itself doesn’t pique your interest, Mystic will invariably encapsulate an ideal picture of a New England small town. In fact, it ranks as one of the best places to live with lots of people moving in from out of town. It’s one of those places that you don’t want to leave after checking out the great restaurants , cute places to stay , and all-around charm!

Mystic was once one of the most important seaports in Connecticut. Much of the maritime history is preserved in the Mystic Seaport Museum. Exhibitions detail lots of information about its history. And just outside the building are several preserved ship museums, many of which are listed on the National Register of Historic Places.

In a port that built hundreds of ships, you’ll still find boats floating around the harbor awaiting new passengers. Go for a cruise on a historic sailboat or steamship and have unbelievable views of the town’s waterfront against the lush trees in the backdrop.

You might even recognize a few places like the Mystic Pizza shop, featured in the popular Julia Robert’s movie of the same name. And if you like marine life, the Mystic Aquarium is one of the best in New England and home to majestic beluga whales.

Mystic has plenty of options for where to stay, but The Whaler’s Inn is the perfect historic inn to match this historic CT seaport town!

If you like historic Connecticut towns, you’re going to love this one! Guilford was settled in 1639, and it has one of the most precious village greens in the region. You’ll see when you arrive, it is about as charming as charming can be.

One of New England’s oldest landmarks is located in Guilford, and it’s a definite must visit. The Henry Whitfield House was built in 1639 and is a history lover’s dream. It is located just down the street from the Guilford Green!

Visit the Village Chocolatier for some tasty treats, then head to the Guilford Art Center to enjoy local art before heading out to Jacob’s Beach for views of lovely Long Island Sound. There’s such lovely coastal scenery in this area of CT!

Looking for where to stay? Check out the Carriage House at Granite Lodge !

Madison is one of the larger towns on this list, with over 18,000 people living there. But what will really blow your mind is that every year, it receives over one million visitors – a majority arriving during the peak summer season. If you couldn’t figure it out by now, Madison is a cute town with picturesque beaches lining the entire shoreline.

Madison is located on the shore of the Long Island Sound. One of the main attractions is Hammonasset Beach State Park . Of all the big and small towns throughout Connecticut, Madison has the biggest beach, extending for two miles. So even with all the tourist traffic, there’s still plenty of room to sunbathe on the golden sands and go for a refreshing swim in the pristine blue waters.

There’s nothing better than taking a stroll through town to admire all of the cute New England-style buildings. There are several cultural venues highlighting art, music, performance, and more. The shops and galleries are excellent places to see the work of local artisans. And some fantastic shows and events happen at the Madison Arts Barn and Madison Art Cinemas all year long.

You’ve got options when it comes to where to stay in Madison, but you should know it is home to one of the dreamiest bed and breakfasts in the state, The Scranton Seahorse Inn .

Wethersfield

Founded in 1638, Wethersfield has the distinction of being the oldest historic district in Connecticut, and it’s lovely for anyone looking for historical preservation at its finest!

There are several beautifully preserved historic homes in Wethersfield, including the Webb Deane Stevens Museum . The grounds and gardens are absolutely gorgeous at this museum, too.

In fact, there is a historic home in Wethersfield that is also a popular place to stay: The Silas W. Robbins House Bed & Breakfast . This is truly one of the most beautiful places to stay in Connecticut, so if you can swing it, we say go for it!

Old Saybrook

It’s hard to say whether Old Saybrook was as stunning in the past as it is today, but there’s something about the old town charm and landmarks that make it one of the prettiest places to visit in Connecticut today.

Old Saybrook was settled in 1635, making it one of Connecticut’s oldest towns. It’s strategically positioned at the mouth of the Connecticut River as it flows into the Long Island Sound. The position was an ideal location for Fort Saybrook, which now operates as a monument park.

Saybrook has one of the cutest lighthouses in the state called the Breakwater Light. I recommend visiting during the evening to see one of the prettiest sunsets you’ve ever seen. The picturesque scenery could easily become your next postcard.

Old Saybrook has a popular public beach called Harveys Beach, where the views are absolutely phenomenal. A few steps from the coast and you’ll be in the heart of town.

Beautiful colonial-era buildings line the small streets as you make your way to popular attractions like the Katherine Hepburn Cultural Arts Center. Dubbed ‘The Kate,’ the former town hall building now served as a performance venue for concerts and recitals.

If you’re able to spring for it, book the Saybrook Point Resort & Spa !

Glastonbury

If a cute town is what you’re seeking in Connecticut, look no further than Glastonbury . Not only is it a charming town in the present day, but it’s one of the oldest settlements in the United States.

A simple stroll around town will reveal why I had to include it on this list. And be sure to have your camera handy because there are tons of gorgeous architectural structures worth stopping to admire.

 Of all the small towns of Connecticut, Glastonbury has some of the most striking colonial-style houses. There are over 150 homes, some dating back as far as the 1600s – some of the oldest houses in the country.

You can see other unique structures like the beautiful First Church of Christ. This town is a slice of New England heaven!

Don’t rush out of town too soon. Glastonbury is also known for hosting incredible events throughout the year. It’s a great way to mingle with the locals and enjoy some of the longstanding traditions. The famous Apple Fest happens in autumn with the apple harvest. Also, the Glastonbury Art Walk exhibits public art installations all around town for a blend of culture and history.

Looking for cozy boutique inn vibes? You’ll find them at Connecticut River Valley Inn !

One of the most lovely Connecticut towns, Litchfield is a fantastic addition to any CT trip. You’ve got all the quaint small town things to do like strolling downtown, scoping out local history at the Historical Society & Museum and the Litchfield Historic District.

Litchfield is also home to the Haight-Brown Winery , Connecticut’s first winery! Today, you can enjoy the picturesque vineyard views while wine tasting or having a lovely meal at the cafe onsite. In the winter they even offer warm spiced wine that can be enjoyed by the roaring fire. How darling is that?

There are several phenomenal restaurants in Litchfield , so pace yourself! But for breakfast, you’ll want to have booked a room at the gorgeous Litchfield Inn – guests rave about their breakfast!

Visit Putnam in any season, and you’ll be amazed at how beautiful the town is. It’s located in the state’s northeastern region, surrounded by scenic nature. From the lush greenery in the summer to the colorful fall foliage in the fall, take a trip upstate to visit one of Connecticut’s cutest small towns.

Putnam is located along the Quinebaug River. The river is just one of the many natural landmarks. It’s surrounded by extensive forested areas where you can enjoy lots of outdoor recreation—one of the top destinations is the Putnam River Trail. Hiking, biking, and swimming are just a few of the recreational activities you can enjoy.

There are also tons of things to do in town. Putnam is full of art and culture. You can check out popular venues like the Bradley Playhouse and the Complex Performing and Creative Arts Centre for live shows year-round.

Just like many other small towns in Connecticut, Putnam too has exciting festivals that happen annually. Head to Main Street for the car cruise or stick around for the light parade during the holidays.

Looking for places to stay near Putnam? This beautiful lakefront cottage could be perfect!

No, not that one, the one in Connecticut! Washington is a teeny tiny CT town that goes all in on charm. You’ve got so many quaint small things to do, like boutique shopping, perusing local art, enjoying the natural scenery of the area, and more.

In fact, this little town is home to a very interesting museum: The Institute for American Indian Studies . With artifacts and exhibits dedicated to preserving and sharing the history of the native people of the area, this is a definite must visit during a Washington trip. They have a replicated 16th-century Algonkian village that’s particularly impressive.

Interested in staying in the inn that is said to have provided the inspiration for the Gilmore Girls? Then you should book The Mayflower Inn , ASAP!

Small towns in Connecticut cannot get smaller than Cornwall; there’s just over one thousand people living there. It’s a friendly little place with a rural community and the cherished covered bridge landmark. What can be cuter than Connecticut covered bridges?

Cornwall is a former farming town that had a brief moment of manufacturing. Now, it reverted to its roots and remains a quaint little town that’s self-sustainable. It has three main districts, each with its own characteristics. The favorite areas are the West Cornwall commercial district and Cornwall Village.

The most popular attraction in town is the Cornwall Bridge . This cute bridge is also one of the last remaining covered bridges in CT. It was built in the mid-1700s and is still used today. However, most people check it out for photos against the landscape backdrop.

During your visit, you’ll have fun recreational activities available on the Housatonic River. It’s popular for kayaking, canoeing, fishing, and camping. The locals are always hanging out, especially during the warmer seasons.

Stop by West Cornwall to browse the quaint shops full of cute souvenirs or diners serving delicious New England cuisine.

As for where to stay in this area, it’s hard to find a more adorable spot than Cornwall Inn !

Okay, Bethel isn’t one of those small towns in CT with a ton of things to do, but it’s got some cool stuff happening!

Step back in time by heading to the Sycamore Drive In Restaurant , Bethel’s drive in that seems to have been frozen in time. You can go for breakfast, lunch, or dinner, but you should definitely try the house made root beer; the recipe has been a local favorite for 75+ years!

Bethel is also home to Blue Jay Orchards , the 122 acre working farm and orchard where you can participate in idyllic small town activities like apple picking. How fun is that?

Looking for a place to stay in Bethel? Microtel Inn & Suites has free breakfast!

Located in Connecticut’s “Quiet Corner,” Woodstock is an absolutely gorgeous place in the Nutmeg State. Visit historic Roseland Cottage then swing by Woodstock Orchards to see what’s in season for their You Pick items. This is always a classic small town CT activity!

When it’s time to refresh, that’s easy. You’ve got Taylor Brook Winery and Taylor Brook Brewery situated right across the road from one another, so you can sample the flavors of the area easily!

As far as where to stay goes, The Watson Boutique Bed & Breakfast is absolutely lovely, and if you’re planning a CT couples trip, it’s perfect.

Milford is one of the cutest small coastal towns in Connecticut. If it feels like you’re walking around an early English settlement, it’s because it’s one of the oldest towns in the state, with many buildings preserved since they were built. While there are many cool things to do in Milford , there are indeed things that you don’t want to miss.

Milford has a shoreline extending approximately 17-miles. Beaches line the entire coast along the Long Island Sound.

An insider tip: Silver Sands State Park has the best beaches in town that I’m sure you’ll love! It also has the longest boardwalk. The beaches are perfect for sunbathing, swimming, and fishing. If you need a break from the water, head downtown and pop into one of the cute ice cream shops. Grab a few scoops and stroll around town to enjoy the charming New England vibes.

A couple of the must-visit attractions are the Audubon Coastal Center to see all the pretty birds from the observation deck or a quirky site like the PEZ museum. Take advantage of the Milford Welcome Center to find out everything happening around town.

Book a room at this gorgeous beachfront cottage if views of Long Island Sound sound like a fantastic accompaniment for your morning coffee!

Nestled inside the Connecticut River Valley, the town of Chester will quickly become your favorite. Whether driving into town through the lush forest region or cruising in on the Chester/Hadlyme Ferry, you’ll be blown away by its charm the moment you lay eyes on it.

Chester is a historic town, first settled in 1692. With many historic buildings remaining, it looks exactly how you’d imagine an old town in New England. The quiet atmosphere and friendly people make it a relaxing place to visit.

Explore town to experience all that it has to offer – from history to culture. You’ll find many buildings listed on the National Register of Historic Places, including the Old Town Hall for its significance and private residences showcasing stunning architecture.

In fact, you can even stay at The Millhouse in downtown Chester, a beautifully renovated historic millhouse turned upscale lodging!

Hand around Main Street to find quaint boutique shops to explore or dine at award-winning restaurants. Many of the businesses are in preserved 19th Century buildings. Honeycone Craft Ice Cream is a must visit!

Small towns in Connecticut like Chester are popular for arts. There are plenty of art galleries around town showcasing local art talent. And if you’re lucky, you’ll get to attend a live performance showing at the Norma Terris Theater, part of Goodspeed Musicals.

Click Here to Check Prices & Book The Millhouse!

Killingworth

Now, Killingworth is a very small town in Connecticut, but it’s got something that is the perfect example of small town sweetness: a lavender farm! Until you’ve walked up and down the rows of fresh blooming lavender at Lavender Pond Farm , you might not understand what makes this such a spectacular draw, but trust us, it is!

You’ll find other cute small town things to do in Killingworth, like visit lovely Chatfield Hollow State Park and explore! There’s a water wheel, covered bridge, and plenty of great walking trails.

For a unique place to stay, book a room at Chatfield Hollow Inn , a wilderness lodge that provides the perfect spot to enjoy the natural scenery of the area.

There are small towns all around the state, but we’ve tried to round up the very cutest, most interesting for you here. Hopefully this Connecticut small town guide will help as you plan your next trip!

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Visit Connecticut’s Hidden Gems this Fall

last updated: January 2024

Each fall, people visit Connecticut to see brilliant displays of foliage in every corner of the state. But even if you live here, there may be a few spots in Connecticut that you’ve never seen, and the fall season is a great time to discover them for yourself. Here are just a few hidden gems worth exploring during the fall. If you find a few more worth recommending, share them with us @CTvisit.com!

Just be sure to check with each location before venturing out as hours may change.

Hawk Ridge Winery, Watertown

Hawk Ridge Winery, part of Hidden Breeze Farm, offers a peaceful farm setting to enjoy friends, family, and fantastic wine. Lounge in their open lawn seating, admire stunning foliage views, sip on the festive wine slushie of the month, and even take a bottle home!

Comstock Covered Bridge, East Hampton

Although the red covered bridge in West Cornwall, Connecticut, tends to get a little more attention, this pretty vintage covered pedestrian bridge across the Salmon River in East Hampton is worth a visit, especially in the fall. 

Powder Ridge, Middlefield

Although primarily a skiing spot, Middlefield’s Powder Ridge has reinvented itself as a year-round destination, offering mountain bike trails that are particularly fun during the colorful fall season. In October, they host an Oktoberfest celebration. Ride the lift up and hike down, or bundle up and get in a few last bike rides in before the snow flies.

Ballard Museum of Puppetry, Storrs

If Halloween has whet your appetite for fanciful characters, take a trip to the remarkable Ballard Museum of Puppetry in Storrs. Experience the past, present and future of puppetry at this unique museum, exhibition, theater and workshop space located on the UCONN campus. Be sure to check the website for upcoming performances as well. Currently open by appointment only.

The Glass House, New Canaan

For something truly unique, visit The Glass House, built between 1949 and 1995 by architect Philip Johnson. The pastoral 49-acre landscape comprises fourteen structures, including the Glass House (1949), and features a permanent collection of 20th-century painting and sculpture, along with temporary exhibitions. The campus serves as a catalyst for the preservation and interpretation of modern architecture, landscape, and art. And you can bet you'll spot beautiful foliage from any direction you look!

New England Motorcycle Museum, Rockville

There’s nothing like a motorcycle ride on Connecticut back roads to really get a feel for the beauty of fall. If you’re looking for a new destination, the largest motorcycle museum on the east coast has recently opened in Connecticut. Housed in Rockville’s 200-year-old Hockanum Mill, you’ll find a collection of over 100 vintage motorcycles and memorabilia on display.

Vanilla Bean Café, Pomfret

Drive along National Scenic Byway Route 169, and you’ll find the Vanilla Bean Café in pretty Pomfret. This award-winning café, named "”Connecticut's Best Country Café” by Yankee Magazine , features hearty sandwiches, homemade soups, baked goods and more, in the heart of Connecticut’s Quiet Corner.

Adventure Park at Storrs, Storrs

For a different kind of scare this season, zip on over to Adventure Park at Storrs  for ziplining through the foliage.

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These Are The 12 Most Beautiful Towns In Connecticut You Should Visit

• Key takeaways:
• Connecticut offers a variety of beautiful small towns with charming natural and historic beauty, including Kent, Chester, and Essex.
• These towns provide a range of activities such as hiking, visiting state parks, exploring local restaurants and shops, and enjoying the scenic waterfronts.
• Each town has its own unique character and attractions, making them ideal destinations for day trips or longer weekend getaways.

Besides its delightful New England charm, Connecticut offers a lot of fun things to do that can be seen everywhere, from its picturesque beachy scenery to its forested hills and its rolling farmland to its mountains, rivers, and seaside waterfronts. And there’s no better way to appreciate the state’s signature beauty than by checking out one of its most beautiful small towns—here are some of the very best.

UPDATE: 2023/09/04 13:26 EST BY NICHOLAS MAYAMBA

Most Beautiful Towns In Connecticut To Visit

Connecticut is a lovely New England state with charming small towns that place tourists in the middle of nature. From lush forests to sprawling lakes, this updated article highlights the prettiest towns in Connecticut worth checking out.

Related: 10 Most Beautiful Hikes You Can Do In Connecticut

Famous for its fabulous fall foliage , Kent is a quaint Connecticut charmer whose lush scenery is a sight to behold—and not just when the leaves are at their best and brightest. A lovely town center completes this picture-perfect New England town, while a plethora of nearby outdoor attractions means there’s always something to see and do.

• Things To Do: Macedonia Brook State Park; Kent Falls State Park; Bull’s Bridge; House of Books; Kent Falls Brewing Co.
• Wine & Dine: Kingsley Tavern; Swyft; Sophie’s Restaurant & Bakery
• Stay The Night: The Victorian; Fife Country Inn

Its rolling hills and scenic Connecticut River setting make Chester a quaint rural retreat full of natural and historic beauty. But that’s not all: once a hub for shipbuilding and milling, the picturesque town is now home to an up-and-coming local art and culture scene that’s all Main Street USA charm.

• Things To Do: Gillette Castle State Park; Pattaconk Reservoir Trail; Little House Brewing Company; Godspeed Musicals at the Terris Theatre; Chester-Hadlyme Ferry
• Wine & Dine: The Village Bistro; Grano Arso; Thai Riverside
• Stay The Night: Copper Beech Inn (10 minutes); Boardman House (15 minutes)

The coastal town of Westport is all seafront scenery and colonial charm—and perfectly placed for a road trip to the Big Apple (50 miles away!), It’s the perfect weekend getaway from the city. Brimming with small-town beauty, Westport also has plenty of attractions to entice vacationers who like their R&R with a side of creativity and culture.

• Things To Do: Westport County Playhouse; Westport Museum for History and Culture; Compo Beach; Earthplace; Sherwood Island State Park
• Wine & Dine: Rive Bistro; Little Barn; Pane e Bene
• Stay The Night: The Inn at Longshore; Hotel Zero Degrees (10 minutes)

Colonial charm meets waterfront beauty in the pretty Connecticut town of Essex. The perfect place for both day trips and (long) weekends, visitors will enjoy strolling the picturesque harbor, admiring the historic architecture, and enjoying the fun shops and restaurants in the town center of this cozy rural retreat.

• Things To Do: Essex Steam Train & Riverboat; The Pratt House; Connecticut River Museum; Falls River Preserve; The Pratt House
• Wine & Dine: Scotch Plains Tavern; Carlson’s Landing; Tap Room at The Griswold Inn
• Stay The Night: The Griswold Inn; Old Lyme Inn (10 minutes)

A charming historic district—including the second-longest green in New England —gives the seafront setting of Milford quintessential small-town vibes. Full of character and idyllic beauty, plenty of eclectic shops and eateries are here to keep visitors busy when they’re not out on the water (or simply admiring its beachy beauty).

• Things To Do: Old Town Milford; Milford Historical Society House Tours; Silver Stands State Park; Eisenhower Park; The Coastal Audubon Center at Milford Point
• Wine & Dine: Founder’s House Pub & Patio; Bonfire Grille; Bridge House Restaurant
• Stay The Night: Homestead Inn; The Blake Hotel (20 minutes)

Wethersfield

An idyllic natural setting complete with tree-lined streets and lush landscapes makes Wethersfield one of the most beautiful towns in Connecticut—and the rural retreat. But there’s more to this beauty than meets the eye; the small hamlet also has a storied past, evident in everything from its plethora of architectural wonders to its many historical heritage sites,

• Things To Do: The Broad Street Green; Wethersfield Heritage Walk; Heritage Way Bike Route; Heirloom Market; Old Wethersfield Historic District
• Wine & Dine: The Charles; Lenoci’s Italian Kitchen; Kaliubon Ramen
• Stay The Night: Silas W. Robbins House; Goodwin Hotel (10 minutes)

Though just a short train ride from NYC, the cozy Connecticut town of Greenwich is all small-town charm: from its historic buildings to its Main Street USA vibes. But Greenwich’s location near the Big Apple also gives it a somewhat metropolitan flair seen throughout its distinctive local shops, boutiques, and eateries.

• Things To Do: Greenwich Avenue and Historic District; Greenwich Point Park; Putnam Cottage Tour; Babcock Preserve; The Flinn Gallery
• Wine & Dine: Le Fat Poodle; L’escale Restaurant & Bar; Elm Street Oyster House
• Stay The Night: Delamar Greenwich Harbor; The J House Greenwich

RELATED: This Quirky Connecticut Book Barn Might Be The Place For Book Lovers

With a location at the foothills of the Berkshires and housing much of Mohawk State Forest, it’s no surprise that Cornwall is famed for its scenic natural setting. And this forested beauty is not just easy on the eyes, it’s an epic outdoor playground, too—complete with plenty of year-round recreation opportunities for everything from biking to skiing.

• Things To Do: Mohawk Mountain Ski Area; Mohawk State Forest; West Cornwall Covered Bridge; Housatonic Meadows State Park; Bike the Western New England Greenway
• Wine & Dine: frank.food company; The Village Restaurant (10 minutes); When Pigs Fly South Southern BBQ (15 minutes)
• Stay The Night: Cornwall Inn; Winvian Farm (20 minutes)

Old Saybrook

Quintessential New England waterfront vibes abound in the pleasantly idyllic Old Saybrook . Think all the frills of a harbor town, like timeless charm, scenic seaside beauty, and locally-owned storefronts that make this welcoming community perfect for a day away—or a long (relaxing)weekend stay.

• Things To Do: Harvey’s Beach; Fort Saybrook Monument Park; Visit Essex Village; The Katharine Hepburn Cultural Arts Center; Rocky Neck State Park
• Wine & Dine: Alforno Trattoria; Little Pub Old Saybrook; The Essex
• Stay The Night: Water’s Edge Resort & Spa; Saybrook Point Resort & Marina

RELATED: It's Rumored That Captain Kidd's Famous Treasure Can Be Found On This Connecticut Island

Though the bustling CT town of New Haven is right on its doorstep, the picturesque and pretty Branford has a distinctly charming small-town feel that can be seen everywhere, from its bucolic beaches to its stately homes. From basking in beachy vibes to trekking the town’s scenic trail, this lovely suburb has it all.

• Things To Do: Branford Trail; Cruise to Thimble Islands; Shore Line Trolley Museum; Branford Point Beach; Stony Creek Brewery; Branford Supply Pond Park
• Wine & Dine: Home; Rosso Vino; Mosaico Cuisine
• Stay The Night: Owenago Inn; Thimble Islands Bed & Breakfast

Tourists will be hard-pressed to find a more charming Connecticut town than Mystic. Its rich maritime heritage is evident at every street corner, from the numerous sea-related museums that dot the town to the different annual events honoring boats and pirates. Whether looking to stay on dry land or venture out at sea, there are endless fun things to do in Mystic .

• Things To Do : The Seaport Museum, Olde Mystic Village, The Mystic Aquarium, Historic Ship Nautilus & Submarine Force Museum, Mystic Downtown Marina, Mystic Museum of Art
• Wine & Dine: Mystic Pizza, Trattoria Amalfi, The Mariner
• Spend The Night: Hilton Mystic, Steamboat Inn, Taber Inn And Suites

A sweet escape from the rigors of daily urban life, this sleepy town in the Connecticut countryside offers a therapeutic dose of natural beauty and small-town charm. Surrounded by sprawling hills and sparkling waters, Colebrook is the perfect playground for nature lovers and comes to its own during fall when hues of yellow, red, and orange highlight its lushly forested spaces.

• Things To Do: Lake Triangle Dam, Algonquin State Forest, Colebrook River Lake, Peoples State Forest
• Wine & Dine: Barnstormer's Burgers & More, Colebrook Store
• Spend The Night: Days Inn by Wyndham Torrington, Royal Coachman Tavern

• 6 Most Scenic Small Towns in Connecticut

Connecticut may be a small state, but there is a ton of stunning natural scenery. From rivers and lakes to mountains and stretches of forests, Connecticut is brimming with natural beauty. One of the best places to enjoy the serenity that nature in Connecticut offers is in the state's small towns. In small towns such as Kent, you can enjoy rugged, beautiful landscapes with waterfalls while immersed in local history. In Essex, you can see a town so charming it inspired the hometown in the television show Gilmore Girls. From historic buildings to a walk on the riverside, the small towns in Connecticut are undeniably scenic destinations. Here, we will explore the top six scenic small towns in the Green State.

Kent is a quiet town with a population of under 3,000. However, despite its small size, Kent is a scenic place. Being near two state parks, the town is full of ruggedly beautiful scenery. Some of the state's best waterfalls are at Kent Falls State Park. Here, you can see waterfalls and covered bridges and explore miles of trails. Kent is also near Macedonia Brook State Park and the East Kent Hamlet Land Trust. These are both great places to enjoy a stroll through amazing natural scenery. Besides the natural scenery, Kent has some interesting history to explore. Visit the Kent Historical Society to learn more about the town's history. Eric Sloane Museum is another historic site where visitors can see the artist's work. The historic site contains his collection of early American tools, his artworks, his pioneer cabin, and the remains of the Kent Iron Furnace. This is significant since they are some of the first ironworks in the state.

Another scenic Connecticut town that attracted artists is Chester . Built in the hills on the side of the Connecticut River , Chester is a mix of forests, rivers, and historic sites. Near the town, there are wonderful natural sites to enjoy, including Cockaponset State Forest and the Selden Neck State Park. Both spots are great places to enjoy hiking, cycling, or camping. One of the must-visit attractions in town is Gillette Castle State Park. The medieval-style castle in the park is a stunning architectural attraction. There are trails to enjoy and amazing picnic spots to enjoy some lunch. For a unique experience, take the Chester-Hadlyme Ferry to reach the castle. Here, you will get a stunning view of the castle from the water. Another historic building to enjoy in Chester is the Goodspeed Opera House. The venue dates back to 1877 and is a great place to enjoy a local show today.

Just ten minutes outside Chester is another scenic Connecticut town, Essex . The cute town is recognizable as the location that may have inspired the famous Stars Hollow town in Gilmore Girls. Stepping into Essex is like stepping into the past. The town has an enduring historic charm, with old farmhouses from the Revolutionary War and other historic buildings. The First Baptist Church of Essex is a popular spot to visit. It is one of three Egyptian Revival churches built in the entire United States. Those looking for an old-timey feel should pay a visit to the Essex Steam Train. The original 19th-century railway locomotive gives a nostalgic tour of the area. Learn more about the history of the area by visiting the Connecticut River Museum. Here, enjoy the lovely view of the water and learn about Native American history, the river, and the local ecosystem. You can also appreciate the riverfront views in Essex by walking on the harbor. There are some nice photo opportunities at the harbor next to the cute little Essex Reef Lighthouse.

Chaplin is a quaint town with a population of under 2,500 residents. The town is a close-knit community with lovely historic buildings and natural places. Two notable places to visit in town are the Chaplin Historic District and Witter House. The Georgian architecture in these spots is from the 19th century and is something to admire. These are also great spots to learn more about the town's history. One of the most scenic aspects of Chaplin is the rural nature of the town. There are many forested areas to explore. Some of the most popular include Diana's Pool and James L. Goodwin Forest.

Those going to Connecticut for the mountains should pay a visit to Cornwall . The town has a hidden gem, one of the last covered bridges in the state. The West Cornwall Covered Bridge is 172 feet long and 15 feet wide and is on the National Register of Historic Places. Beyond the bridge, people come to Cornwall to experience the area's green scenery. Full of mountains and forests, Cornwall is a hiker's haven. A popular hike to do in town is the Pine Knob Loop Trail. Located in Housatonic Meadows State Park and Housatonic State Forest, the short hike is challenging, with rewarding mountain views. The Housatonic River has a section that runs through Cornwall. Paddling, fishing, and hiking are popular activities around the river.

Another town with stunning outdoor scenery in Connecticut is Madison . Madison is a beachside town near Long Island Sound. There is plenty to do in town to enjoy the scenery, including fishing, surfing, hiking, and picnicking. The Shoreline Greenway Trail is a popular place to enjoy a walk with shoreside views. Madison is near plenty of beaches, including Hammonasset Beach State Park, Surf Club Beach, East Wharf, and West Wharf. To explore and learn about nature in town, check out Meigs Point Nature Center. Those who are more interested in staying inside can still enjoy the town. The downtown has several cute shops to explore, including boutiques, bookshops, and restaurants. Movie lovers should check out the Madison Art Cinema. The local theater dates back to 1912 and is independently run. The interior of the theater is uniquely designed with a stunning color scheme of aquamarine, antique gold, and a tone of red.

Ultimately, these six small towns are some of the most scenic in Connecticut. Many of the towns have a mix of stunning natural scenery and unique historic architecture to admire. While all these towns have beautiful natural scenery, they are all quite different. Some of the towns, such as Cornwall, showcase the mighty Connecticut mountains. Others, such as Madison, show the relaxed, beachy environment the state can have. Chester, on the other hand, is a balance of natural beauty and architectural marvel. Overall, these towns all offer a unique experience of the state.

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Outdoors | Lace up your boots and take a hike this spring…

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Outdoors | shots-fired incident prompts investigation in new london, outdoors | lace up your boots and take a hike this spring season at one of these 18 ct trails.

The Nutmeg state hosts numerous well- and lesser-known trails , giving hikers a bevvy of choices to enjoy all the natural beauty the state has to offer. Coupled with warming spring temperatures and blooming foliage, now makes a perfect time to lace up your hiking boots and take a trip through Connecticut’s picturesque wilderness.

If you are looking for a new trail to explore or want to spend the day with nature, we have got you covered.

Here is a list of 18 trails to check out across Connecticut.

Talcott Mountain Yellow Trail in Simsbury

Located just a couple towns over from Hartford, Talcott Mountain Yellow Trail is a 2.8-mile trek perfect for beginners or those looking for a quick hike. Make sure you keep your dog on a leash if you bring your furry friend.

Stoney Lonesome Trail, Norfolk

What better way to avoid crowds than to head to the  “Stoney Lonesome” trail  high above Norfolk into East Canaan.

Laurel marsh trail in manchester.

Another easy-going trail for the whole family, Laurel Marsh should take hikers around an hour to complete its 3.4-mile loop. It is a popular trail for runners, too, as well as birding.

Sunnybrook State Park, Torrington

Nestled in Torrington,   Sunnybrook State Park   includes trails that run along the banks of the East Branch of the Naugatuck River.

Mattabesett and mount higby trail in middlefield.

Looking for a long hike? Mattabesett’s 9.3 miles of scenic Connecticut foliage is a great choice to soak in a crisp fall day. It is also a popular birding destination, so bring your camera.

Kensington Orchards Preserve, Berlin

A hike through the  Kensington Orchards Preserve  in Berlin offers some spectacular views. It also provides the opportunity to hook up with miles of trails in the Chotkowski Conservation Area and Camp Meribrite.

St. Johns Ledges to Glacier Rock in Kent

While a bit of a hike from Hartford, Kent is one of Connecticut’s most beautiful towns. Traveling the 8.6-mile trail of St. Johns Ledges should take seasoned hikers roughly five hours to complete. Bring your canine companions, too; just make sure they are leashed.

Scantic River State Park, Enfield/East Windsor/Somers

The Scantic River State Park encompasses more than 780 acres spread across three towns, but for the purposes of this list, we look specifically at Enfield, where, Scantic River Linear Park West features scenic views of the river, a farm, a forest filled with huge white pines.

Jessie gerard trail in barkhamsted.

While only 3 miles, Jessie Gerard Trail can be more challenging for less experienced hikers. Even so, expect a shorter hike compared to the longer trails, with plenty of opportunities for photography and birding. If you plan on bringing a dog, make sure they stay on a leash.

Sprague Land Preserve, Sprague

There are 11-12 miles of trails available in the sprawling  Sprague Land Preserve  in the eastern part of Connecticut.

Chauncey peak trail in meriden.

While on the shorter end, Chauncey Peak Trail will take you around the Bradley Hubbard Reservoir: a beautiful body of water to compliment the colors of autumn. This 2.3-mile hike will take you right back to where you started. Feel free to bring your pet as well; there are even some areas where they can be off-leash.

Derby Greenway Trail, Derby

A 1.7-mile paved multiuse path  runs along the top of dikes high above the Naugatuck River and Housatonic River.

Peak mountain via metacomet trail in east granby.

Pet-friendly and close to the heart of Connecticut, Peak Mountain is a great choice to get in a satisfying hike. Make sure you have your camera ready for this 3.7-mile out-and-back trail.

Horse Guard State Park, Avon

Horse Guard State Park  Scenic Reserve doesn’t have elaborate trail systems, vast parking lots, websites and detailed maps and facilities. But, it does offer one of the best views in Avon and a respite from large crowds.

Cedar mountain loop in newington.

Short and sweet, Cedar Mountain Loop is an easy-going choice for families and folks new to hiking. The entire 1.1-mile route should take less than an hour to complete, giving you time to snap a few pictures and explore the state’s natural beauty.

Suburban Park, Unionville

Along the 4 miles of trails you’ll find the remnants of an abandoned 20th Century amusement park, glacial kettle holes and the scenic Roaring Brook .

American Legion State Forest, Barkhamsted

There are a pair of trails in American Legion State Forest – Henry Buck and Turkey Vulture Ledges. The Henry Buck trail is a 2.3-mile loop while the Turkey Vulture is a mile-long out and back path.

Black Rock State Park, Watert o wn

The 439-acre Black Rock State Park offers beautiful overlooks. The main hiking trail – the Connecticut Forest and Park Association’s blue-blazed Mattatuck Trail – is approximately a half-mile from an iron bridge at the northern end of the pond. It’s a half mile uphill and will give visitors a workout.

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The 10 Most Walkable Cities in Connecticut

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Connecticut , a state known for its rich history and picturesque landscapes, is also home to some of the most walkable cities in the country. From the vibrant cultural hub of New Haven to the bustling city life of Hartford, each city offers a unique blend of walkability and affordability.

In this Redfin article, we delve into the top 10 most walkable cities in Connecticut , providing insights into their walk scores and real estate market. So, if you’re considering a move to the Constitution State, this guide will help you find the perfect city that matches your pedestrian-friendly lifestyle.

1. New Haven, CT

Walk Score: 68 Median Sale Price: $320,000 Median Rent Price: $1,875

With a walk score of 68, New Haven is the most walkable city in Connecticut. Home to Yale University, the area boasts several pedestrian-friendly neighborhoods like Wooster Square and Downtown. These areas contain a variety of shops, restaurants, and attractions easily accessible on foot.

Find New Haven, CT homes for sale or apartments for rent .

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Walk Score: 67 Median Sale Price: $255,500 Median Rent Price: $1,350

Hartford has a walk score of 67, making it the second most walkable city in the state. There are numerous walkable areas and neighborhoods throughout Hartford , like Asylum Hill and Downtown, helping make the city explorable without a car.

Discover Hartford, CT homes for sale and apartments for rent . Check out which Hartfort neighborhoods are the most walkable.

3. Bridgeport, CT

Walk Score: 66 Median Sale Price: $350,000 Median Rent Price: $1,750

Bridgeport is the most populous and third most walkable city in the state. Particularly walkable neighborhoods in Bridgeport include Downtown, Black Rock, and The Hollow. These places are home to amenities like Seaside Park, Captain’s Cove Seaport, and the Barnum Museum.

See Bridgeport, CT homes for sale or apartments for rent . Check out which Bridgeport neighborhoods are the most walkable.

4. Stamford, CT

Walk Score: 55 Median Sale Price: $570,000 Median Rent Price: $2,912

Stamford has plenty of amenities a resident might need well within walking distance. From Harbor Point to Downtown, there’s something for every lifestyle. The downtown area is particularly walkable, with numerous restaurants, shops, and attractions.

Search for Stamford, CT homes for sale and apartments for rent .

5. New London, CT

Walk Score: 55 Median Sale Price: $248,000 Median Rent Price: $1,500

As the fifth most walkable city in the state, New London is known for its historic waterfront district and vibrant arts scene. Consider exploring Ocean Beach Park or getting a bite to eat at Fred’s Shanty with friends. Or if you’re in the mood for an adventure, visit Fort Trumbull State Park.

Brose New London, CT homes for sale and apartments for rent .

6. Manchester, CT

Walk Score: 52 Median Sale Price: $273,500 Median Rent Price: $1,800

Manchester, a suburb of Hartford, has a walk score of 52, making it the sixth most walkable city in the state. There are numerous walkable areas and neighborhoods throughout Manchester, like the Downtown Historic District and Buckland Hills, helping make the city explorable without a car.

Find Manchester, CT homes for sale and apartments for rent .

7. Willimantic, CT

Walk Score: 50 Median Sale Price: $248,500 Median Rent Price: $1,250

Willimantic, a suburb of Hartford, is the seventh most walkable city in the state. Particularly walkable areas in Willimantic include Downtown and the Eastern Connecticut State University area. These places are home to amenities like the Windham Textile and History Museum, Cafemantic, and the Air Line State Park Trail.

Discover Willimantic, CT homes for sale or apartments for rent .

8. Norwalk, CT

Walk Score: 48 Median Sale Price: $555,500 Median Rent Price: $2,700

Norwalk, a suburb of Stamford, has plenty of amenities a resident might need well within walking distance. From SoNo to Rowayton, there’s something for every lifestyle. The downtown area is particularly walkable, with numerous restaurants, shops, and attractions.

Peruse Norwalk, CT homes for sale or apartments for rent .

9. New Britain, CT

Walk Score: 48 Median Sale Price: $285,000 Median Rent Price: $1,400

As the ninth most walkable city in the state, New Britain is known for its vibrant arts scene and historic architecture. Consider exploring Walnut Hill Park or getting a bite to eat at Staropolska Restaurant with friends. Or if you’re in the mood for an adventure, visit the New Britain Museum of American Art.

Find New Britain, CT homes for sale and apartments for rent .

Thinking about moving to the area?

10. west haven, ct.

Walk Score: 48 Median Sale Price: $303,000 Median Rent Price: $1,750

West Haven, a suburb of New Haven, is the tenth most walkable city in the state. Particularly walkable areas in West Haven include the University of New Haven area and the Savin Rock neighborhood. These places are home to amenities like the Savin Rock Conference Center, Jimmies of Savin Rock, and the West Haven Green.

See West Haven, CT homes for sale or apartments for rent .

Want to learn more about getting around in the Constitution State? Check out the most bikeable cities in Connecticut .

Methodology: Walk Score , a Redfin company, helps people find a walkable place to live, rating areas from least to most walkable on a scale from 0-100. To calculate a Walk Score for a city, Walk Score analyzes thousands of walking routes to nearby amenities, population density, and metrics such as block length and intersection density. Points are awarded based on the distance to amenities in each category.

Jamie is part of the content marketing team and is passtionate about climate change, housing affordability, and housing market trends. His dream home is a small, modern, and minimalist forested home where he can hear the wind blowing at night.

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