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Sleepy Hollow, NY: Your Guide to Halloween Season

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In recent years, travelers have finally learned that there is more to the great state of New York beyond our buzzing city. One place in particular has been on a lot of globetrotters’ radar, and that place is Sleepy Hollow, New York.

Where to go for Vacation in October

If you are like me seeking where to go for vacation in October, Sleepy Hollow is THE place to be in September and October.  It embodies all of the things that we love about the fall – the things that, quite honestly, we could really use after the last two years of pandemonium. Cozy little restaurants, an abundance of nature (leaf peeping!), and good old-fashioned Halloween fun!

Plus, it’s only an hour past New York City, making it accessible for East Coasters and those already visiting the area.

If Sleepy Hollow has been on your radar, use this guide to plan your perfect trip there this fall.

Where is Sleepy Hollow?

Sleepy Hollow is a small village in the Hudson Valley area of New York State. It is so named because of the famous writer Washington Irving who lived in the area and wrote “The Legend of Sleepy Hollow.”

It’s important to note that Sleepy Hollow proper is actually quite small. The surrounding towns are only a few minutes away. They’re so close that you really won’t be able to tell where one begins and the next ends. Tarrytown, Elmsford, and Ossining are all suitable places to lodge and eat when visiting Sleepy Hollow.

Sleepy Hollow Experiences.

Now, let’s look at some of the best things to do in Sleepy Hollow, New York:

The Great Jack O’Lantern Blaze:

Perhaps the most sought-after experience in Sleepy Hollow is the Great Jack O’Lantern Blaze. While many cities are offering similar experiences, there’s something extra special about visiting the one in ‘Halloween Headquarters.’

Artists begin carving pumpkins in the summer and by October, THOUSANDS of them are lit and make their appearance for tons of spectators to enjoy. The level of intricate detail and craftsmanship is awe-inspiring. One of the most remarkable facets is how many pumpkins are used often to create one larger piece, such as a giant carousel, a re-creation of a famous art piece, or a cultural tapestry.

Grab tickets to this one early. It’s something that you’ll remember for a lifetime.

Sleepy Hollow Cemetery Tours:

Typically we might think of cemeteries as places that are uncomfortable. The cemetery in Sleepy Hollow is one of the most beautiful that I’ve ever seen. It’s truly akin to an outdoor art museum as many of the crypts, tombs, and headstones are so intricately crafted, unique, and impossibly precise. Be sure to walk around during the day to gain a real appreciation.

However, at night, it’s imperative to take a spooky walking tour through the cemetery. You’ll hear all about the incredible ways that people who now lay in its confines perished and left this world. The tour guides even give you an old-style lantern to carry around as you hear each of the tales.

Irving’s Legend:

The entire town of Sleepy Hollow exists largely because of “The Legend of Sleep Hollow.” It’s a horror story written by Washington Irving in the 19th century. It has since reached international fame, with the tale translated into a multitude of languages. Countless adaptations for the screen and stage having been created.

During Halloween season, watch one of the most gifted story tellers in the United States re-tell the beloved classic. He’ll leave you laughing, on the edge of your seat, and, of course, a little spooked.

Washington Irving’s Sunnyside Estate:

On a chilly fall day, there’s nothing more dreamy than touring the home and grounds of the infamous Washington Irving. Smiling attendants are usually selling warm cider and snacks for you to enjoy before or after your tour. Costumed docents walk you through the home. It’s fun to imagine the infamous American author, his family, and guests cozying up in the small rooms of the estate as the ghoulish wind whips by and the mighty river churns outside. Don’t forget to catch the finger puppet performance of “The Legend of Sleepy Hollow” while you’re there!

Tarrytown Music Hall Ghost Tours:

The music hall theater is over 130 years old, so you know that there’s bound to be some interesting history. You can learn all about what went on during all of those years inside of the theater. Plus, you’ll hear about its many secrets, and best of all, learn about the other-worldly spirits that still haunt the premises. Guests are led by Gotham teams who allow their groups to use special advanced technology to find paranormal spirits within the music hall. What’s extra-spooky about this attraction, however, is the price tag attached…$135 per person. But, it’s an amazing experience!

Sleepy Hollow Haunted Hayride:

This is another event that only takes place at the end of October. This year it’s on October 22nd and 23rd. The hay wagon takes guests down lively Main Street, past the Old Dutch Church, and into the spooky, dark woods of the hollow. The hayride retraces the path Ichabod Crane took as he tried to outrun the Headless Horseman.

Farmer’s Markets:

TaSH Farmer’s Market and the Irvington Farmer’s Markets are the two in town to visit. Both feature just about every yummy and beautiful natural product you can imagine, from cheese to wine to bread to fresh-cut flowers. Locally grown produce makes a wonderful souvenir that won’t take up room in your living space nor gather dust for years to come.

Hulda’s Night:

Everything here circles back to “The Legend of Sleepy Hollow.” In the story, the author mentions that the town was under the spell of a “high German doctor.” There are many who think that he’s alluding to a healer woman from Central Europe. She lived in Rockefeller State Park, and if you hike through Witch’s Spring Trail, you can walk by the area that used to be her dwelling.

In this experience, guests go to that same trail and hear all about her life and story. Drinks and snacks are given at the end of the storytelling. Unfortunately, this is another one limited to just a few days at the end of October. It’s October 27 through 30th with two shows per evening at 6:00PM and 7:00PM.

Halloween Parade: 

Each year, towards the end of October, the Village of Tarrytown hosts a Halloween parade. It starts by Patriot’s Park and heads down Main Street. Afterwards, there’s a giant block party with a DJ and performances. Most people choose to wear their costumes, so don’t be shy about wearing yours!

The parade is on October 23rd this year at 5:30PM.

Sleepy Hollow Film Festival:

This year, the Sleepy Hollow Film Festival is from October 15th through the 17th. On the Sleepy Hollow waterfront, a pop-up drive-in theater will show pieces submitted by contestants. I’ll be updating this as more information comes out!

Not Running for 2021.

The following experiences are unfortunately not running for the 2021 season, but I’ve included them for future visits to Sleepy Hollow.

Horseman’s Hollow:

This one is a ‘spooky walk’ or haunted house type experience. In front of the Philipsburg Manor is a re-created Sleepy Hollow village from the 1700s where everyone has ‘gone mad’ from the Headless Horseman. Costumed actors roam around and pop out to scare guests. There’s some serious talent in the construction of ‘haunted’ places like a chapel and spooky cabins.

Sleepy Hollow Experience:

If you’ve ever been to an immersive theater show, then you know how utterly and insanely captivating the performances can be. This immersive version of “The Legend of Sleepy Hollow” often sells out but it is not to be missed. Guests follow all of the characters from the story through every scene of the tale, and even get to hang out and have some treats at the grand Van Tassel harvest party.

Old Dutch Church Fest:

This event takes places on the grounds of the Old Dutch Church which is actually part of the setting of the Legend of Sleepy Hollow. Guests can buy sweets, ciders, beer, sausages, hot dogs, and souvenirs. Most proceeds go to the upkeep of the adjacent cemetery which houses graves of many folks, including patriots of the American Revolutionary War.

If you’re familiar with Edgar Allan Poe, then you’ll at least remember hearing the phrase ‘nevermore.’ It comes from his chilling piece of writing entitled “The Raven.” Nevermore is a theatrical and aerial arts/circus-style adaptation of that Poe classic. Watch acrobats soar as they re-tell the story set to spooky music.

Not-So-Spooky Places to Visit in Sleepy Hollow.

And finally, here are some things to do in Sleepy Hollow, New York that aren’t so spooky:

Sleepy Hollow Lighthouse Tours: 

The Sleepy Hollow Lighthouse has been in use for eighty years and was rendered obsolete in the early sixties due to the Tappan Zee Bridge being built with navigational lights which serve the same purpose as the lighthouse. Learn about the dozen or so lighthouse keepers and their families when you take a tour.

The Octagon House: 

Few houses are more intriguing than the Armour-Stiner house. Built in the pre-Civil War period, its pink walls and unusual shape give the building a playful, antique, borderline spooky appearance. It’s modeled after the style of ancient temples and with such a storied history, it feels just as old. While you’re not able to visit and enter on your own, you can book a tour and learn all about the history of the house!

If you’ve ever wondered how the other half lived, now is your chance. Kykuit was the home to four generations of Rockefeller family members. Thanks to the remaining descendants, guests have the opportunity to walk through the mansion and grounds on guided tours. You’ll truly be in awe as you see the modern amenities of the time that the family used inside their home as well as the many rooms (more than you’d even know what to do with) and their lavish aesthetic. Hearing stories about the family humanizes them a lot, as most people see them as celebrities. The house is furnished to look exactly as it would have when the original family members were living within its walls.

Old Dutch Church:

This church has a history that dates all the way back to the late 1600s. Its name comes from when the Dutch Merchant Company ruled New York before the British. Walk on the creaking floor boards, listen to the wind howl outside the fragile windows, and admire the centuries-old organ. Outside, you can explore the 2.5 acres of cemetery and rolling green land. The church is a focal point of Washington Irving’s classic, “The Legend of Sleepy Hollow.”

Union Church of Pocantico Hills:

This church really just fits the entire aesthetic of Sleepy Hollow. It has a rustic charm that fits right into the surrounding nature. It also has a bit of a storied history connecting directly to the Rockefeller family and Henri Matisse. There are usually events here such as book sales where you can find gently used novels for a dollar apiece.

If you’re into castles that looked as though they’re plucked from the pages of a storybook, then you’ll really enjoy Lyndhurst. Built in the mid-1800s, it’s had a few ‘who’s who’ of owners, including Jay Gould, the railroad baron. Take a tour of the opulent inside, walk around the gardens, and partake in the many fairs that take place on the grounds.

Places to Stay in Sleepy Hollow.

To fully experience Sleepy Hollow, you’ll need to spend a few days there. I recommend booking your hotel well in advance if you plan to visit during the busy Halloween season!

Budget Option:

Don’t want to break the bank? No problem, book a stay at…

We’ve snagged a room here for under $100 and enjoyed it very much. It’s no frills, but warm, cozy, and a fine place to watch Hocus Pocus after a cemetery walk or evening meal.

Moderate Options: 

If you want a few more amenities, consider one of these mis-range accommodations:

Comfort Inn and Suites:

Very clean, and extremely comfortable beds. The best part about staying here is the great amount of space that you’ll have. That’s especially important if you’re traveling with a family.

Courtyard Marriott:

A fireplace in the lobby and lots of space for relaxing, enjoying a quick breakfast, or getting some work done makes this a comfortable option. Guest rooms are clean, usually come with a desk, and offer just enough space (although not a ton of it).

Hampton Inn:

If you’ve stayed at a Hampton Inn, then you know. Clean and a decent amount of space. There are sundries for sale if you need some snacks or basic toiletries.

Luxury Options:

Finally, if you want to stay in style, check out one of these options:

Hotel Nyack:

If you’re into hotels with aesthetic appeal, this is the place for you. It’s industrial enough to feel as though it belongs somewhere in Brooklyn, yet offers balcony views of the Hudson River. The rooms feel extra luxurious with chandeliers, high-backed chairs, and wallpaper that gives serious ‘boudoir’ vibes.

Sleepy Hollow Hotel & Conference Center:

Roaring stone fireplaces, high wooden beamed ceilings, and dark cherry stained features make this place feel  like it belongs in Sleepy Hollow. Cool amenities include a gorgeous indoor pool and gym. The rooms are oh-so-spacious and full of warm, autumn colors.

Tarrytown House Estate:

This estate boasts over 200 guest rooms and 10 Georgian style rooms. The ambiance is minimalist meets artistic, and the pale colors and bursts of white make it feel sparkling clean. The King House Mansion which houses some of the rooms was constructed in 1840. There’s a basketball court, horseshoe court, tennis court, indoor and outdoor pools, a restaurant, and a fitness center.

Castle Hotel and Spa:

This place is quite literally a castle. It’s decorated with cozy fireplaces, luxurious comforters on four-poster beds, and candelabras hanging from the ceilings. With sweeping views of the New York City skyline, Hudson River, and Palisades, this makes it an extra luxurious option for lodging.

Places to Eat in Sleepy Hollow.

Of course, no travel guide would be complete without discussing local food options!

Pik Nik BBQ:

My personal favorite spot for lunch! It’s a full sensory experience with perhaps the best playlist ever created, the smell of smoked meats wafting through the air, and the taste of slow roasted pork, creamy mac and cheese, and tangy apple coleslaw. Ribs, chicken, andouille sausage, burnt ends, cornbread, potato salad, everything barbecue classic is available for your gastronomic pleasure. Be aware that space can be limited.

Lefteris Gyro:

Another exceedingly popular spot that has limited seating, but at least it’s both indoor and outdoor. I love this place, and from experience I can say that you need to order enough food so that you can literally roll out when you’re done. The shrimp saganaki is potent, pungent, and bursting with flavor — personally I’d choose it every time. If shrimp isn’t your thing, don’t worry, there’s what feels like dozens of other options, much more than your typical Greek restaurant. The avgolemono soup (lemon chicken) warms both the bones and the soul. It’s a nice light option. Have a glass of wine with dinner and a Greek frappe or coffee (careful there) for after your meal.

Goosefeather: 

This restaurant has both indoor and outdoor seating and is a MUST if you’re looking for savory, decadent, comfort food. The menu is Hong Kong inspired and you’ll want to order the shaved snow peas, sweet summer corn, and Cantonese roast duck, in addition to the delicious dim sum offerings. For dessert? Mochi waffles, of course.

Horsefeathers:

Dimly lit, warmly inviting, and Halloween-esque, this is a MUST visit in Sleepy Hollow. Cider, beer, and adult juice boxes are the name of the game in terms of booze. For sustenance, you can visit for brunch, lunch, or dinner. The menu feels endless (there are over a hundred items) and includes lots of options by way of pasta, meat and poultry, seafood, burgers and sandwiches, and salads. When dessert rolls around, opt for a boozy coffee — there are seven versions to choose from!

Guadalajara:

Make reservations in advance, because this popular Mexican eatery is packed nearly every night in October. Whatever you order, rest assured that it will be awesome. In my humble opinion, you have to start your meal off with the guacamole prepared table-side and the queso fundido (the best I’ve ever had). The tortilla soup is a heavenly second course and although you’ll be full, make room for an entree — it’s worth it. Margaritas pack a punch here and come in a variety of flavors.

Visiting during October is extra special because every staff member dresses up in costume complete with elaborate make up!

Sweetgrass Grill:

The food at this light, airy beach restaurant is seasonal and locally sourced from farms nearby. For brunch try the lemon blueberry waffle or the heirloom tomato hash (yum!). Salads and sandwiches make up the majority of the menu which makes this a great lunch spot (even for takeout).

Tarry Tavern:

Situated right on Main Street, this place isn’t a bad choice at all for a lunch with some upscale options. Picture a place that serves comfort food, and then levels up that comfort food — like mac and cheese with crab meat and white truffle, for instance. Pork cheeks, sea scallops, burrata cheese, duck confit fettuccine, and Amish roasted half-chickens are just a fraction of the elevated comfort food that makes up this menu.

J.P. Doyle’s:

A beer garden meets Irish tavern that has all of the classics – burgers, Reubens, potato skins, and more. Don’t miss their brunch or taco Tuesday specials – that one comes served with a side of trivia!

Bridge View Tavern:

Despite being a ‘tavern,’ the fare goes way beyond buffalo wings and mozzarella sticks. Try options like fig and goat cheese flat bread, curry vegetables, a wild boar chorizo burger, or elk burger. This is by no means an exhaustive list of entrees, but as you can see, the menu is anything by typical. Of course you’ll want to get a beer, cider, or mixed drink, such as a grapefruit martini, to wash it all down.

Hudson Farmer and the Fish:

Hudson Farmer and the Fish sits on the Hudson’s riverbank and featured a seasonal menu. Unsurprisingly given the restaurant’s name, there’s a heavy focus on locally sourced seafood – both raw and cooked. There’s also a pizza menu selection that will have you saying, “well…what’s the harm in ordering ALL of them?” Good luck deciding between options like the Clam (clams, bacon, celery, onion, thyme, garlic, fontina and parmesan) or the Mushroom (truffle, arugula, fontina, and portobello mushrooms).

Hudson Anchor Seafood and Grill:

Looking for a meal with a gorgeous view? You’ve found the right place. The menu has some more ‘mature’ offerings like panzanella salad, paella, and seafood risotto, but by no means is the atmosphere stuffy. String lights, wide umbrellas, and decorative fall touches like hay bales and corn stalks give this place an intimate, laid-back vibe.

Coffee and Such in Sleepy Hollow.

If you just need a cup of coffee and a snack, head to one of these local gems:

Coffee Lab Roasters:

An absolute favorite among locals and visitors alike, maybe because it’s puppy themed?! Enjoy knock out coffee and pastry options like almond or chocolate croissants, Scottish short bread, and cake pops. They offer unique and healthy coffee options like CBD vanilla and golden turmeric.

Muddy Water Coffee & Cafe:

Whether you want a cozy meal, sweet pastry, or just a coffee pick-me-up — this is a great spot for something quick and something that is made with love and care!

Places to Drink in Sleepy Hollow.

And finally, you’ll likely want to check out some of the area’s breweries after a long day of exploring!

Sing Sing Kill Brewery:

Looking for a brewery that doesn’t frown on bringing your kids along? Visit Sing Sing! Enjoy decadent options like Cherry Chocolate Milk Stout or Killer Cream Ale and get some hot dogs and soft baked pretzels to go with your brews.

Speaking of kids, here’s what you need to know if you’ll be visiting Sleepy Hollow with little ones.

Beekman Ale House:

Beekman Ale House knows that the people love Halloween! Throughout the month of October, Beekman’s celebrates Pumpkin Fest with a series of rotating beers on tap that are all pumpkin flavored. When you’re getting good and buzzed, order any of the five twelve-inch pies on the menu (hot oil flavor is a good choice) or classic apps like mozzarella triangles and wings. The wooden interior and neighborhood vibe give this bar a cozy, fun ambiance.

Captain Lawrence Brewing Company:

As far as craft beers go, Captain Lawrence is becoming increasingly popular. With flavors like Autumn Blaze Pumpkin Ale, Golden Delicious Tripel, and a host of IPAs and sours, it’s no surprise. Aside from tasting fantastic brews, Captain Lawrence Brewing Company offers fun opportunities like trivia nights and live music.

People to Follow.

Want to know more about Sleepy Hollow and the neighboring areas and attractions? These are the places I turn to get excited about the upcoming season! Follow these accounts on social media:

Sleepy Hollow Spellbound 

Visit Sleepy Hollow  

Tarry In Town

TarryHollow Town  

• September 16, 2021

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Stephanie Amb

Stephanie is a writer of travel, fiction, and New York lifestyle. She currently lives in Brooklyn and teaches full time in Queens. She is a wife and mother to one son. Stephanie is a co-founder at Tawk of New Yawk and her work has been featured in Your Life is a Trip, Teaching Traveling, and Literary Traveler.

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Ultimate Guide to Halloween 2021 in Sleepy Hollow and the Rivertowns

By Brianna Staudt —

Whether you’re a local anticipating a favorite Halloween tradition or a visitor looking to experience Halloween in Sleepy Hollow Country for the first time, The Hudson Independent has you covered. Read below for all the tricks, treats and haunts in Sleepy Hollow, Tarrytown, Irvington, Dobbs Ferry and the surrounding area.

Please note this list will be updated as additional events are confirmed. Required pandemic precautions are included.

The Tarrytown Halloween Parade and block party have been cancelled.

Horseman’s Hollow, the Old Dutch Church Fest and Jay Ghoul’s House of Curiosities are also not running this year.

The Sleepy Hollow Tarrytown Chamber of Commerce is staffing its office at 1 Neperan Road in Tarrytown on Saturdays 9 a.m.–1 p.m. throughout the fall to help visitors navigate local businesses. Stop by for maps, recommendations and parking information.

TarryHollow Walking Tours Tour #1 starts at 11 Dell Street/418 North Broadway Sleepy Hollow Sept. 5-Nov. 14, Saturdays and Sundays; 10 a.m., 12:30 p.m. 3 p.m. $24.99/ticket https://www.thehistoricalsociety.net/events/tours-tarryhollow/ Travel back in time with the Tarrytown and Sleepy Hollow historical society on a 1.5- or 2-hour tour of the area. The Hudson Independent recommends Tour #1: “TarryHollow: Irving, the Old Dutch Church and the Colonial Experience” for Halloween fun, though there are three popular tours available. Arrive 15 minutes early for check-in. Advance reservations required; purchase tickets online. Private tours available.

Evening Lantern Tour Sleepy Hollow Cemetery North Gate 540 North Broadway Sleepy Hollow Friday and Saturday nights in September; every evening in October; weekends and select weekdays in November. Times vary. $30 https://www.showclix.com/event/classic-evening-lantern-tour-2021 Explore the historic Sleepy Hollow Cemetery by the light of a kerosene lantern. This one-hour tour focuses on the north end; visit during the day to see Irving’s grave. Ages 10 and up.

The Great Jack O’Lantern Blaze Van Cortlandt Manor 525 S. Riverside Croton-on-Hudson Sept. 17-Nov. 21, select nights $24; members and children 2 and under are free https://hudsonvalley.org/events/blaze/ Breath-taking display of over 7,000 jack-o’-lanterns, which are hand-carved and arranged on-site. New installations for 2021 include the New York City skyline and an “immersive” river display. Tickets must be purchased in advance.

Champagne Cocktails with the Dead Sleepy Hollow Cemetery – North Gate 540 North Broadway Sleepy Hollow Sept. 26 and Oct. 3, 5-7:30 p.m. $85 https://visitsleepyhollow.com/events/champagne-cocktails-with-the-dead/ Peak inside mausoleums and learn family histories, champagne cocktail and/or light refreshment in hand. No jeans or shorts, but comfortable walking shoes are recommended. For ages 21 and up; masks required in the mausoleums.

Fall Reflections: An Installation Lyndhurst Mansion, Rockery Pathways 635 S. Broadway Tarrytown Sept. 30-Oct. 31, 9:30 a.m.-4:30 p.m. Free with purchase of a grounds pass ($10; children 6 and under and Lyndhurst Members are free) https://lyndhurst.org/events/outdoor-decor/ Discover witches and other spirits in the fall landscape south of the mansion. New for 2021: a special art installation from LiteMirror .

Home of the “Legend” Washington Irving’s Sunnyside GPS address: 3 West Sunnyside Lane Irvington Oct. 1-Nov. 8, Fridays-Sundays and Columbus Day; entries 10 a.m. – 3:30 p.m. $10-$12 https://hudsonvalley.org/events/home-of-the-legend/ Tour the first floor of Irving’s home and learn how “The Legend of Sleepy Hollow” has lived on in popular culture. Family friendly.

Irving’s “Legend” Washington Irving’s Sunnyside GPS address: 3 West Sunnyside Lane Irvington Fridays-Sundays Oct. 1-31, 6:30, 8 and 9:30 p.m. $24-$35 https://hudsonvalley.org/events/irvings-legend/ Master storyteller Johnathan Kruk performs “The Legend of Sleepy Hollow.” Live music and an appearance by the Headless Horsemen himself. Tickets required and must be purchased online in advance. Appropriate for all ages.

“Myths and Mysteries” Tour  The Armour-Stiner Octagon House 45 W. Clinton Ave. Irvington Oct. 1-31; multiple dates and times $27-29 https://www.showclix.com/event/myths-mysteries Explore this 1860 historic home with a one-hour tour featuring its “connection to the spiritual world,” including “unexplained and uncanny” events. Is there a resident ghost? Masks required; not suitable for individuals with mobility difficulties.

Pumpkin Painting and a Hayride Devries Park 139 Devries Ave. Sleepy Hollow Oct. 2, 11 a.m.-12 p.m. or 12-1 p.m. Free Paint and decorate a pumpkin (pumpkin and supplies provided) and take a hay ride around the park. Presented by the Sleepy Hollow Department of Recreation. Email [email protected] or [email protected] to reserve your time slot. 100 children only per time slot.

Halloween: A Haunted History Virtual Presentation Oct. 4, 7 p.m. over Zoom Free This new program traces the “strange history” of Halloween, from Old World festival to modern holiday. Presented by the Warner Library. Registration required.

Halloween Crafts Warner Library 121 North Broadway Tarrytown Oct. 6, 4 p.m. Free Come to the children’s garden to make spooky — not scary — Halloween decorations using recycled materials. For ages 3 and up. Registration required and limited. Call the children’s desk.

Murder & Mayhem Sleepy Hollow Cemetery North Gate 540 North Broadway Sleepy Hollow Thursdays, Oct. 7-Nov. 11; 7:30-9:30 p.m. $45 https://www.showclix.com/event/murder-mayhem-2021 Two-hour, lantern-light walking tour of the cemetery’s darker history, including the scene of a grave robbery and victims of  the “Mad Murderer of Sleepy Hollow.” Ages 18 and up. Please note this event is an approximately 1.5-mile walking tour in the dark that includes steep hills and stairs.

Scarecrow Making Parking Lot D (to the right of the recreation department) 238 W. Main St. Tarrytown Oct. 9, 10:45-11:45 a.m. or 12-1 p.m. Free Register by Oct. 7 at this link (space is limited): https://tarrytown.seamlessdocs.com/f/qyeh2no2hgky Make a scarecrow to be displayed by the village along Main Street or Broadway. Straw, bags, ties and frames will be provided. Participants bring their own clothing, scissors and markers. Participants may also choose to pick up supplies, build their scarecrow at home, and drop it off by 1:30 p.m. Masks required.

Paint your own Witchy Wonderland Washington Irving Memorial Chapel 540 North Broadway Sleepy Hollow Oct. 9, 12-3 p.m. $65 https://www.showclix.com/event/paint-your-own-witchy-wonderland-2021 Join painter Heather Gleason to create your own Halloween canvas — paint, brushes, canvas and light refreshments included. Age 18 and up. This event takes place inside and requires masks regardless of vaccination status.

Halloween Slime Warner Library 121 North Broadway Tarrytown Oct. 12, 4 p.m. Free Gather in the children’s garden to make a jar of Halloween slime. For grades 1-5. Registration is required and limited. Call the children’s desk.

Sleepy Hollow International Film Fest Kingsland Point Park Sleepy Hollow Oct. 15-17; cars may arrive starting 5:30 p.m., first feature at 7:30 p.m. $25/car each night http://sleepyhollowfilmfest.com/horseless-carriage-cinema/ Outdoor double-features and food trucks. Movies include The Thing and Arachnophobia — see website or flyer for complete list of titles per night. Must purchase tickets in advance online and bring a printed copy. Audio available via radio; if you’re not planning to view the movie from inside your car, make sure you have a device that picks up FM radio.

Outdoor Screening of Hocus Pocus Main Street School Lawn 101 Main Street Irvington Oct. 15; Doors open for “treats” and a red carpet at 5:30 p.m., movie starts at sunset $5/ticket (must be purchased in advance via website) https://www.irvingtontheater.com/hocuspocus Presented by the Irvington Theater as part of its “Sunset Cinema” series. Attendees should bring blankets and chairs. Outside food is allowed, however, there is no alcohol allowed on school grounds. Don’t forget your costume!

Mary Shelley’s Frankenstein Washington Irving Memorial Chapel 540 North Broadway Sleepy Hollow Oct. 16, 5:30-7 or 8-9:30 $25 https://www.showclix.com/event/mary-shelley-s-frankenstein-2021EttIsCo Enjoy an adapted presentation of this classic tale. Event is seated indoors; masks required regardless of vaccination status.

“Trunk-or-Treat” Lot F (parking lot between the boat club and Losee Park) Green Street Tarrytown Oct. 17, 4:30-6:30 p.m. Free Drive-thru format: families drive through the lot to view the decorated trunks and pick up treats along the way. Register your decorated vehicle to distribute candy on the Tarrytown Recreation website by Oct. 14. Contest for best vehicle. Presented by the Tarrytown Recreation Department.

Harvest Hayride Matthiessen Park 1 Bridge St. Irvington Oct. 17; family rides 6-7 p.m., haunted rides 7-8:30 p.m. Free Come for a horse-and-wagon ride, refreshments and music by the Blu Road Orchestra Band. Masks must be worn while waiting online. No dogs. No pre-registration required. Presented by the Irvington Recreation Department.

Halloween Window Painting Main Street and Broadway Tarrytown Oct. 20, 3:30-5:30 p.m. Free https://www.sleepyhollowtarrytownchamber.com/event-details/tarrytown-halloween-window-art-1 Help paint store windows on Main Street and Broadway! Children pickup paint in front of CVS on North Broadway between 3:30-4:30 p.m. Reserve your window at the link above — registration required. Parent/guardian supervision, masks and social distancing required. Presented by the Tarrytown Recreation Department.

Halloween Party Warner Library 121 North Broadway Tarrytown Oct. 21, 4 p.m. Free Gather on the front lawn in costume for a story, treats and crafts. Ages 3 and up.

Halloween Terrariums Irvington Library 12 S. Astor St. Irvington Oct. 21, 5:30-6:30 p.m. Free Make something fun (and a little spooky) for Halloween. In the program room; masks required. For grades 6-12. Registration required.

Pumpkin Painting for Teens/Pre-Teens Dobbs Ferry Library Terrace 55 Main St. Dobbs Ferry Oct. 22, 4:30-6 p.m. Free Paint a miniature pumpkin outside on the terrace. Light food and beverages provided. E-mail [email protected] to register.

Sleepy Hollow Block Party Beekman Avenue Sleepy Hollow Oct. 22-23, starting 5 p.m. Free Vendors, music and more

Haunted Hayride Sleepy Hollow Village Hall/Firehouse 28 Beekman Ave. Sleepy Hollow Oct. 22-23, 7 p.m. – 12 a.m. $40/ticket; $20 rate for Public Schools of the Tarrytowns students if tickets purchased at Village Hall before noon Oct. 22 with student ID. https://sleepyhollowny.ticketleap.com/2021-sleepy-hollow-ny-haunted-hayride/ Face masks required. This event is not recommended for some children due to graphic content. Tickets required and must be purchased online in advance. Act fast — tickets sell out!

Sleepy Hollow Halloween 10K & Kids Fun Run W. L. Morse School 30 Pocantico St. Sleepy Hollow Oct. 23, 10K 9:30 a.m.; Fun Run 9 a.m. $40 registration through Oct. 17; $50 registration on race day. $5 for Fun Run. http://www.rivertownrunners.org/sleepy-hollow-10k/ This 10K winds through historic Sleepy Hollow with sites including the Sleepy Hollow Cemetery, the Old Dutch Church, the Headless Horseman Bridge and a beautiful stretch along the Hudson River. Registration capped at 1,500 runners. Mile-long Kids Fun Run is for ages 6 and older includes a finisher medal. Costumes encouraged for runners of all ages but not required. Live music, and beer tasting for runners age 21 and older. Please note no strollers, inline skates or pets are allowed.

Outdoor Halloween Movie Night: Hotel Transylvania Pierson Park 238 W. Main St. Tarrytown Oct. 23, movie starts at 6:30 p.m. Free Popcorn will be served. Bring blankets and chairs. Attendees are encouraged to support local restaurants and bring meals and snacks to the movie. Presented by the Tarrytown Recreation Department. No tickets or registration required.

Ghost Tours of the Music Hall Tarrytown Music Hall 13 Main Street Tarrytown Daytime tours Oct. 24; late afternoon and evening tours Oct. 27-28 $25 https://tickets.tarrytownmusichall.org/eventperformances.asp?evt=2508 “Balcony to backstage” guided ghost tour of the 136-year-old theater. Vaccinated patrons only. Masks required. Flashlights provided for all attendees courtesy of Key Bank. Please note the tour requires stair climbing and standing for extended periods.

Downtown Halloween Window Painting Contest Cedar and Main Streets Dobbs Ferry Oct. 24, 10 a.m.-2 p.m. $5/individual (2nd-8th grades); $7/team (2 people 2nd-8th grades); $10/family (up to five immediate family members) www.dobbsferry.activityreg.com Decorate storefront windows as individuals, teams or families to compete for best in division or three overall prizes: “Most Original,” “Most Whimsical” and “Best Halloween Concept.” Presented by the Dobbs Ferry Recreation Department. Open to Dobbs Ferry residents and Dobbs Ferry school district students only. Must register by noon on Oct. 22. See link above for registration and official contest rules.

2nd Annual SUP Witch Paddle Horan’s Landing 57 River Street Sleepy Hollow Oct. 24, 1 p.m. Free if you own your own SUP board or kayak; $35 to rent equipment https://rivertownssupyoga.com/sup-witches-2021-2 Costume Required. Come to Horan’s Landing to hear a telling of the Legend of Sleepy Hollow. Then, launch with other witches at 5 p.m. on a paddle along the Hudson River shoreline. Paddle experience required. Spectators welcome; the RiverWalk is a prime location to view the paddle. See the Wishing Wall while you’re there.

Halloween Origami Dobbs Ferry Library 55 Main St. Dobbs Ferry Oct. 25-31 Free Stop by the children’s room and check out a special Halloween origami station — fold paper bats, ghost and black cats! Ages 7 and up.

Halloween Story-Time Irvington Library 12 S. Astor St. Irvington Oct. 26, 4-4:45 p.m. Free Come in costume for a story and a treat! In the library garden. Registration required. For ages 4 and up.

Hulda’s Night Rockefeller Park Preserve 25 Sleepy Hollow Road Sleepy Hollow Oct. 27-30; 6 and 7 p.m. programs $28 https://www.friendsrock.org/huldas-night Guided tour through the dark woods to Hulda’s home, where she will tell her story. You’ll meet “The Leatherman” along the way — maybe some other friends, too. Bring a flashlight. No children under 10.

Irving’s Nightmare Presents: The Spider Lab 26 Irving Ave. Tarrytown Oct. 27-31; 6-10 p.m. Free https://www.facebook.com/IrvingsNightmare/ Elaborate local “yard haunt” that never disappoints.

Riverside Haunts The Good Witch Coffee Bar 134 Southside Ave. Hastings-on-Hudson Oct. 28-29, 7 p.m. $25 https://www.eventbrite.com/e/riverside-haunts-scary-stories-to-tell-by-the-hudson-tickets-166176336897 River’s Edge Theater Company hosts two nights of scary storytelling, history and live music outdoors. Recommended for mature audiences only. 10 percent of ticket sales benefit Riverkeeper.

Field of Screams Firehouse Basement 112 Main Street Dobbs Ferry Oct. 29, 7-9 p.m. Free Can you make it through without being scared? Enter on Main Street in front of the police station. Geared toward children age 8 and up. Presented by the Dobbs Ferry Recreation Department. Masks required. This event is usually held at the park but has been moved indoors due to inclement weather.

Halloween in the Children’s Room Dobbs Ferry Library 55 Main St. Dobbs Ferry Oct. 29-31 Free Come in costume and pick out a prize! Ages 0-12.

Halloween at the James Galgano Senior Center 55 Elm Street Sleepy Hollow Oct. 30, 1 p.m.–5 p.m. Free Halloween crafts and treats and photo booth, 1 p.m. in the senior center;  “Truck-or-Treat” in the parking lot, 3–5 p.m. Kids of all ages welcome. No pre-registration required. Presented by the Sleepy Hollow Recreation Department.

Pet Parade Dobbs Ferry Waterfront Park 87 Ogden Park Dobbs Ferry Oct. 31, 11:30 a.m. Free Dress up your pet and meet at the flagpole for a loop around the park to show off their costumes. Dogs must be leashed. Masks recommend for unvaccinated individuals. Presented by the Dobbs Ferry Recreation Department.

Howl-O-Ween Bash Dobbs Ferry Waterfront Park 87 Ogden Park Dobbs Ferry Oct. 31, 12-4 p.m. Free Inflatables, a petting zoo, mini-golf, food trucks and live music by Al Indig & Friends and Marguerite & co. Masks recommend for unvaccinated individuals. Presented by the Dobbs Ferry Recreation Department.

“Howl-O-Ween” Kids Parade 30 Pocantico Street Sleepy Hollow Oct. 31, 3:30 p.m. Free Meet at W. L. Morse School. Candy and prizes — get those costumes ready! Kids of all ages welcomed. No pre-registration required. Presented by the Sleepy Hollow Recreation Department.

Downtown Trick-or-Treating Cedar and Main Streets Dobbs Ferry Oct. 31, 4-6 p.m. Free Music by Rooney Tunes. Masks recommend for unvaccinated individuals.

Irvington Halloween Parade North Broadway and Main Street Irvington Oct. 31, 4 p.m. Free Families should gather in Immaculate Conception Church parking lot. (No pets, please!) The parade will proceed down Broadway and Main until Main Street School. Children can pick up a free treat bag courtesy of the Irvington Fire Company. Presented by the Irvington Recreation Department.

Halloween Bands Downtown Irvington Irvington Oct. 31 evening Free Check out local musical talent perform crowd favorites live in costume on front porches. This much-anticipated event is an annual tradition. Here’s the current lineup: Wild Thyme, Barn Owls, North Dutcher All-Stars, and Evil Eckar w/Death Island and the Dirty Irv Horns. Expect at least one other band on the 31st.

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How to Plan the Perfect Trip to Sleepy Hollow, New York

This small town is a fabled Halloween destination packed with history — and it's less than an hour from NYC by train.

Where to Stay in Sleepy Hollow

Things to do in sleepy hollow, where to eat and drink in sleepy hollow.

• Halloween in Sleepy Hollow
• Best Time to Visit

How to Get There

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Less than 30 miles from Midtown Manhattan lies the quaint village of Sleepy Hollow in Westchester County, New York. Each fall, the otherwise unassuming destination, which has a population of just under 11,000, lures in throngs of thrill-seeking travelers. 

What’s more, explains Natasha Caputo, director of Westchester County Tourism & Film , the dynamic village is renowned for its rich history and deep-rooted connection to Washington Irving's 1820 tale, “The Legend of Sleepy Hollow.” Although a visit to Sleepy Hollow is a must during the spooky season, it’s sure to be crowded, which is why travelers will want to plan ahead as much as possible. With this in mind, we’ve compiled the ultimate guide to Sleepy Hollow during the Halloween season, along with tips, recommendations, and expert insights to help plan your visit any time of year (because it’s not all about Halloween). 

Sleepy Hollow Hotel

The Sleepy Hollow Hotel is one of the village’s very few hotels. The property spans 11 acres of grassy, tree-lined grounds. When guests aren’t out and about exploring, they can be found swimming in the lap pool, relaxing in the sauna, or digging into breakfast staples like omelets and fresh-baked pastries at the charming Bistro Z Restaurant. 

Tarrytown House Estate on the Hudson

A few minutes down the road in nearby Tarrytown, travelers can choose from historic hotels with castle-like exteriors. Tarrytown House Estate on The Hudson is ideal for families with its year-round indoor pool (there is also an outdoor pool for adults that’s open seasonally) and on-site sports like tennis, racquetball, bocce ball, and volleyball. The sprawling 26-acre grounds and the stylish Goosefeather restaurant (which serves traditional Cantonese-style fare with a modern twist) are added bonuses. Lucky visitors may even spot the resident ghost lingering on the second floor of the King House. 

The Castle Hotel & Spa 

The Castle Hotel & Spa is the perfect place for a romantic escape . Surrounded by 10 acres of tranquil woodland, the renovated castle features 31 rooms and suites, some of which boast en-suite fireplaces, marble baths, and four-poster beds. Additional hotel highlights include an upscale American eatery, a spa, a cozy library, and manicured gardens.

John Greim/LightRocket via Getty Images

Kykuit, the Rockefeller Estate

This former residence of the Rockefeller family — including a 40-room mansion and surrounding gardens — is now a historic landmark that's open seasonally between May and November. What’s more, says Caputo, “Its gardens and art collections are truly captivating, making it a must-visit, regardless of the season.” Visitors can choose from a handful of tour options, which can be found online .

Philipsburg Manor

Travelers can visit Philipsburg Manor , a former mill and trading complex owned and operated by the prominent Philipse family, to learn more about the enslaved individuals who lived and worked here in the 18th century. Keep in mind that the site is only open on select dates between May and December.

Old Dutch Church

The Old Dutch Church dates back to 1685 and is most famous for appearing in “The Legend of Sleepy Hollow.” Its 2.5-acre burying ground serves as the supposed home of the Headless Horseman in the spooky tale.

Sleepy Hollow Cemetery  

The historic Sleepy Hollow Cemetery serves as the final resting place for over 45,000 individuals, including Irving. The 90-acre, 1849-era cemetery is open daily from Monday to Friday and offers several types of walking tours .  Just outside the cemetery, you’ll find the iconic Headless Horseman Bridge and the Headless Horseman Statue.

Hudson Farmer & The Fish

Situated on the Sleepy Hollow Riverwalk, Hudson Farmer & The Fish features “seasonal specialties from their farm , along with a full raw bar, pizza, and modern takes on favorite seafood classics,” says Sarah Marshall, senior marketing manager of Westchester County Tourism & Film. While travelers can’t go wrong with anything on the menu, consider trying one of the autumnal-inspired dishes like pumpkin bisque and fall harvest hash. Meanwhile, the beautiful Hudson River views are an incredible added bonus. 

J.P. Doyle's

“ J.P. Doyle's stands out as a charming Irish pub and restaurant, celebrated for its warm and welcoming atmosphere,” says Marshall. Both locals and visitors alike can be found inside this friendly neighborhood haunt. It’s also here where travelers will find one of the best burgers in town (aptly named the Horseman Burger). 

Bridge View Tavern

According to Marshall, beer enthusiasts will especially love Bridge View Tavern for its impressive craft beer selection. Visitors can pair their brews with delicious pub fare like pulled pork sandwiches, disco fries, and chicken wings, which are smoked in-house. 

Hudson Anchor Restaurant

From pasta to steak to seafood, Hudson Anchor Restaurant has it all — not to mention an incredible happy hour special (20 percent off all cocktails, beer, wine, and food at the bar Mondays-Fridays from 3:00 p.m. to 6:00 p.m.). If the weather’s nice, nab a seat on the outdoor rooftop deck. It’s also worth noting that the restaurant’s beloved weekend brunch is unavailable in October.

Santorini Greek Restaurant

Craving Greek cuisine? Look no further than  Santorini Greek Restaurant . Menu highlights include any of the dips (served with fresh pita) and gyros. 

Halloween in Sleepy Hollow 

Given the village’s history, it should come as no surprise that Sleepy Hollow truly comes to life during the spooky season. Expect an array of Halloween-centric events, drawing in hundreds, if not thousands, of tourists. Keep scrolling for a few of the highlights.

The Legend Cirque

This immersive performance , an adaptation of “The Legend of Sleepy Hollow,” is set in the early 19th century and is narrated by Irving himself (in hologram form, that is). It features exhilarating live-action circus performances that’ll have guests at the edge of their seats. The Legend Cirque runs through Oct. 29 and is best suited for those ages eight and up.

The Horsemen: Terror Lies in Chaos

Thrill-seekers need not miss this spectacular haunted house experience , which runs from Oct. 6 through Nov. 5. Located at the Kathryn Davis RiverWalk Center in Kingsland Point Park, this interactive haunted house focuses on finding and destroying a headless horseman (aptly named Chaos). Just keep in mind that this attraction is not for the faint of heart: No one under 16 is allowed without a chaperone; however, per the website , it’s highly recommended that those under 12 sit this one out.  

Sleepy Hollow Cemetery 

To ring in the spooky season, Sleepy Hollow Cemetery hosts an array of special events , including a murder mystery bash and evenings with Washington Irving and Edgar Allan Poe (who are portrayed by local storytellers). For something less scary — albeit just as fun — visitors can partake in an art class to create their own haunted cemetery canvas painting. 

Additionally, as previously mentioned, the cemetery offers a handful of tours to choose from, including several nighttime options, which, per Caputo, are “an absolute must” for  “those with an appetite for the mysterious.” What’s more, she says, “These tours offer a unique opportunity to delve into the lives of its famous residents and learn about the legend of Sleepy Hollow, all beneath the eerie, moonlit skies.” 

SUP Witches Festival

Taking place on Oct. 15, the fourth annual SUP Witches Festival is a sight to be seen. You can watch in awe as a group of “witches” gather to paddle at Horan's Landing – or join in on the fun. (Note that advance registration, as well as costumes, are required.) Even those who don't get in the water can enjoy the event with live music, food, and brews. 

Haunted Hayride and Block Party

Plan your visit for Oct. 20 or 21 to hop aboard the Haunted Hayride , which carries passengers via hay wagon through downtown before detouring past the Old Dutch Church. Eventually, you’ll get through a set of iron gates — before slipping into the darkness with the sound of hoofbeats and shrieks in the distance. Post-hayride, visitors can enjoy the free block party on Beekman Avenue, featuring live music, entertainment, family-friendly activities, and much more.

Sleepy Hollow “Run for Your Life” Halloween 10K 

On Oct. 28, Sleepy Hollow will host its annual “ Run for Your Life” Halloween 10K . The family-friendly event draws kid and adult runners, and for a fun Halloween twist, participants are encouraged to dress up. 

Irving’s Legend at Washington Irving's Sunnyside 

On select dates, visitors can head to nearby Tarrytown to tour Irving’s home , which is decorated in festive fall decor. Caputo tells T+L , “Here, the legend of the Headless Horseman comes to life, enveloping visitors in a chilling narrative that's not for the faint of heart.” While the event is only open through Halloween, the estate itself doesn’t close until Dec. 17. 

Lyndhurst , a historic mansion in neighboring Tarrytown, is also well worth a visit, says Caputo. “The 'Classic Fall Mansion Tour at Lyndhurst' allows visitors to journey through a historic mansion adorned in the splendor of autumn.” Alternatively, plan your visit during the evening hours to check out Lyndhurst After Dark , when the mansion is draped in candlelight. 

Best Time to Visit 

The best time to visit Sleepy Hollow ultimately depends on your interests. For example, those with an affinity for all things spooky will want to travel here during the fall season, “especially in October when the Halloween events and foliage are at their peak,” says Caputo. However, Sleepy Hollow also makes a great weekend getaway any time of year, especially considering its proximity to New York City.  

Visitors arriving by car will find the village conveniently located near major thoroughfares such as I-287 and the Saw Mill River Parkway. “Alternatively,” says Caputo, “for a stress-free journey, you can opt for public transportation by taking a Metro-North train to either Philipse Manor Station in Sleepy Hollow or the Tarrytown station.” Both stations are a short walk or drive from Sleepy Hollow’s most charming attractions. 

It’s also worth noting that Westchester County Airport is just 20 miles away, while other NYC airports like LaGuardia (LGA), John F. Kennedy (JFK), and Newark (EWR) are all within a 45-mile radius. 

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Heading to Sleepy Hollow for Halloween? Here's what to see and do

Come October, this Westchester village along with its neighbor Tarrytown, becomes Halloween central, based around its long history and as the setting for Washington Irving's famed "Legend of Sleepy Hollow," the tale of the hapless school teacher Ichabod Crane and his nemesis the Headless Horseman. There are myriad things to do in both villages, from walking tours of its historic Sleepy Hollow Cemetery and Old Dutch Churchyard, to ghost tours of the historic Music Hall in Tarrytown to experiencing a Gothic mansion after dark!

While you're there, check out historic sites such as Kykuit, the Rockefeller estate and Philipsburg Manor, a historic 17th century farm and gristmill located across the street from Sleepy Hollow cemetery. Go to historichudson.org for more info on these sites.

There's enough listed here to keep you busy for an entire weekend, but be aware, some dates sell out quickly, so check websites for availability:

Glass Pumpkin Patch, Oct. 14-16

For the first time, visitors can walk through a maze of hay bales featuring special hand-blown glass pumpkins displayed at Kingsland Point Park. Proceeds from the sale of the glass pumpkins benefit the Make-A-Wish Hudson Valley Chapter. Food trucks will be available. The event is free to the public, although a parking fee will apply. 10 a.m.-5 p.m. Oct. 14 - 16. Kingsland Point Park. Visit glasspumpkinpatchfundraiser.com for more information.

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'The Legend,' thru Oct. 16

Audiences will be treated to a cirque/theatre noir production of Washington Irving's "The Legend of Sleepy Hollow," with narration by Washington Irving himself – in hologram form, commemorating the 200-year anniversary of Irving's spooky tale of Ichabod Crane and the Headless Horseman. Tickets are on sale now at SleepyHollowLegend.com. The show will run through Oct. 16 in the “Legend” Circus Tent on the East Parcel at 60 Continental Street in Sleepy Hollow. Showtimes: Fridays, 7 p.m.; Saturday, 2 and 7 p.m., and Sundays, 2 and 7:30 p.m. Shows run for an hour and a half and include an intermission. Tickets are $30 online and $40 at the door. Recommended for ages 10 years old and up. For more information, contact Westchester Circus Arts at 914-275-5711.

'Hulda, The Other Legend of Sleepy Hollow,' Oct. 15,-16, 22-23, 29-30

Once shunned as a witch, Hulda of Bohemia is now remembered as an 18th-century patriot and healer. This one-woman story telling experience was written by Carla Lynne Hall and Jim Keyes and is performed by Hall with original music performed by Keyes. Performances are held at 1 p.m. and 3:15 p.m. at the Old Dutch Church of Sleepy Hollow, Oct. 15-16, 22-23, 29-30. Tickets are $25 adults; $20 children. The Old Dutch Church is located at 430 Broadway, Sleepy Hollow. Find tickets at tickets.hudsonvalley.org/events

Sleepy Hollow Haunted Hayride & Block Party, Oct. 21,22

The Haunted Hayride legend rides again into the dark night where ghosts and goblins loom. The block party begins at 5 p.m., however, the hayrides have already sold out. Dates: Oct. 21, 22. Block party begins at 5 p.m. For more info, go to sleepyhollowny.gov. No fee for the block party on Beekman Avenue that features food for purchase, music and bouncy castles. 

Hulda's Night, Rockefeller Preserve, Oct. 21,22

Hulda’s Night is an adventure into the history and legends of the Rockefeller State Park Preserve through live performance. As guests hike through the dark woods with lanterns guiding the way, they will encounter various people, from The Storyteller, who recounts legends by fireside to the “witch” herself. Hulda, lonely and gravely misunderstood, awaits to tell you her side of the story. Tickets are $30. For more information, visit:  friendsrock.org

Tarrytown Halloween Parade, Oct. 29

Expect floats, costumed revelers, and bands along Broadway and then down Main Street to a the reviewing stand where prizes will be awarded. Begins at 5:30 p.m. Rain date is Oct. 30. Go to  tarrytownhalloweenparade.com

Sleepy Hollow Cemetery Tours, thru November

This historic cemetery is the final resting place for author Washington Irving, who wrote "The Legend of Sleepy Hollow," as well as the historic 17th century Old Dutch Church. There are several events planned around Halloween, from cocktails with the dead, to a murder mystery, along with daytime and evening walking tours, some led by lantern light. Events take place in September, October and select dates in November. For the complete schedule, a link to purchase tickers and more information, go to  sleepyhollowcemetery.org/walking-tours  or call 914-631-0081. Events, tours begin at Sleepy Hollow Cemetery North Gate, 540 North Broadway. 

'The New York Grimpendium,' Oct. 28

A special treat for Halloween, Lyndhurst welcomes author J.W. Ocker who will give a special talk on all things grim in our region! Based on his bestselling book, "The New York Grimpendium," Ocker will regale visitors with a personalized itinerary of the best grim and spooky sights nearby, including Lyndhurst itself! Talks at 2:30 and 5:30 p.m. Tickets are $30. For tickets, more info go to lyndhurst.org/events. Lyndhurst is located at 635 S. Broadway, Tarrytown.

Ghost Tours of The Music Hall, thru November

If you've been to a performance or show at this historic theater, this is a fun event to experience all its glories and its past! Storyteller Jonathan Kruk leads the 45-minute tour of the historic theater, built in 1885, and home to events as wide ranging as President's speeches to women suffrage rallies; roller skating to movie screenings of "Gone With The Wind." It is a vessel through which many people pass. And some don’t leave … The building is an official site of the Haunted History Trail of New York.  Gotham Paranormal Research Society  has investigated the Music Hall several times and has consistently detected paranormal activity including intriguing EVP (electronic voice phenomena) audio files and EMF (electromagnetic field) readings. Tours may be led by Chant Macleod. 13 Main St., Tarrytown. For dates and ticket reservations, sold online only, not at the box office, go to https://tickets.tarrytownmusichall.org.

Lyndhurst After Dark, Oct. 21-23, 29-30

Tour the mansion once home to Gilded Age financier Jay Gould by candlelight, see rarely viewed special collection pieces on display surrounded by festive Autumnal decor.  Performers will relate in-depth stories regarding  Victorian mourning practices, customs, and spiritualism, a popular social pastime of the era. All visitors must have a pre-purchased ticket for this performance. A limited number of tickets are available and time slots do sell out. For tickets and more info go to lyndhurst.org . 635 South Broadway, Tarrytown

SUP Witches Festival at Horan's Landing, Oct. 16

If you are searching for a wicked sight, come to Horan's Landing for the 3rd Annual SUP Witch Paddle. Witches will gather and "The Legend of Sleepy Hollow," will be told. Join the witches on the water or stroll along the riverwalk. Vendors, food, brews and spooky views are available. Costumes encouraged! All paddlers must register in advance to participate at rivertownssupyoga.com. Noon - 4 p.m. (Rain date October 23.)

The Legend of Sleepy Hollow, thru Oct. 31

Irving’s ‘Legend’ returns reimagined this fall. Performed for the first time ever outdoors under the stars at Washington Irving’s Sunnyside, master storyteller Jonathan Kruk will cast a spell with dramatic performances of the classic tale. Live music and an appearance from the Headless Horseman himself make this a spooky spectacular experience for all ages. Fridays-Sunday thru Oct. 31. Find tickets at hudsonvalley.org/events/irvings-legend/

Tour The Home of the Legend, thru Nov. 13

At this family-friendly happening, visitors can tour Washington Irving’s house — decorated for the season — watch an original shadow puppet short film, and enjoy games on the lawn. A special exhibit highlights how the  Legend  has lived in the imagination of popular culture through the centuries since its publication. Friday-Sunday through Nov. 13. Find tickets at hudsonvalley.org.

Sleepy Hollow 'Run For Your Life' Halloween 10K, Oct. 29

Experience historic and scary sites along the scenic Hudson River course. A best costume prize will be given. Advance registration at rivertownrunners.org. Kids race beings at 9 a.m., 10K at 9:30 a.m. at Morse School on Beekman Avenue.

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Spooktacular Sleepy Hollow at Halloween Weekend Getaway!

Looking to visit Sleepy Hollow at Halloween time? From September through the end of October, Sleepy Hollow and the villages that surround it in the Hudson Valley in Westchester County, New York attract Halloween and spooky season lovers (like us) to enjoy all the legendary spooky folklore and sites in the area, making this area one of the best places to celebrate fall and Halloween in the world!

Located just 30 minutes north of New York City, we are going to cover how to spend a spooktacular weekend in Sleepy Hollow , New York at Halloween time! Plus, we will include a few other incredible local gems around the Westchester County area on your exciting weekend getaway.

For this weekend getaway, we recommend having a car to explore the area as there are some really cool towns in the Hudson Valley to check out, so you’ll have more flexibility in visiting Sleepy Hollow and attractions in the nearby villages of Tarrytown, Croton-on-Hudson, Dobbs Ferry, Irvington, and Yonkers mentioned in this guide. Plus, the fall foliage this time of year is stunning and taking a scenic drive is a part of the magic this time of year here.

Be sure to see our full guide to all the best things to do in Sleepy Hollow & Tarrytown too!

But, wait! There are so many cool things to do in the Hudson Valley you can read about to also add on to your trip or weekend getaway too!

Disclaimer: This trip was in collaboration with Visit Westchester County, as always all opinions and experiences are our own!

A Brief Background of Sleepy Hollow & Nearby Villages of Westchester County

Before we dive into how to spend a fun and spooky time during Halloween in Sleepy Hollow, we want to give a brief background and highlights of the area.

Located along the Hudson River north of New York City and Manhattan, for centuries, this area has attracted the wealthiest entrepreneurs from the city offering a countryside escape from the chaos of everyday life in New York City. You’ll find several historic estates and manors in the area with sweeping views of the Hudson River and Palisades including the estates of famed author Washington Irving, whose creative life work has made this a Halloween destination to this day as well as the estate to the Standard Oil tycoon, John D. Rockefeller. 

In addition to the historic estates and luxurious mansions, Westchester is also known for its charming Hudson River villages, beautiful scenery, and historic sites.

Because we are focusing on the fall and Halloween season festivities, the focal point of this guide will be Sleepy Hollow because it’s the most well-known and famous village in the area, although we will be showcasing nearby sites as well as everything is pretty close to one another and with a car, you won’t be driving more than 20 minutes in between sites at the most.

Sleepy Hollow is famous for its haunting atmosphere, largely thanks to the imagination of Washington Irving, often referred to as the ‘father of American Literature’ who published a series of short stories including, The Legend of Sleepy Hollow and Rip Van Winkle , two of the most well-known short stories and his work would go on to inspire other famed authors like Nathaniel Hawthorne, Herman Melville, and Edgar Allan Poe to name a few.

Irving grew up in Manhattan but built his countryside estate here in Tarrytown, featured later on in this guide, and is buried in the Sleepy Hollow Cemetery where the legendary tale of Ichabod Crane and the Headless Horseman took place, what’s considered the first ghost story in American literature. 

The area and its locals embrace the spooky folklore and legacy here and go above and beyond for the Halloween season! From Halloween decor, haunted sites, a chance to walk through thousands of blazing pumpkins, ghost stories, and more – Sleepy Hollow and Tarrytown have maintained their legendary status around this time of year being truly one of the best places to celebrate Halloween in the world!

So without further ado, here are some of the incredible activities to fill your Halloween in Sleepy Hollow weekend getaway! Be sure to see our guide to the best things to do in Sleepy Hollow and Tarrytown for more ideas of things to include on your trip.

Weekend in Sleepy Hollow at Halloween (& Nearby Villages)

• Visit Sleepy Hollow

If you’re visiting Sleepy Hollow at Halloween, you need to take a stroll downtown, a few of the things mentioned in this weekend guide to the area include a few landmarks in Sleepy Hollow as well. We suggest starting at Beekman Avenue by Broadway where you can enter the ‘downtown area’ of Sleepy Hollow. During Halloween time you’ll spot spooky decor at the Sleepy Hollow clock.

Take a stroll down Beekman to browse the stores, shops, restaurants, and spooky decor downtown! If you’re visiting in the morning, we had a great bagel at Headless Bagel (next to Carvel) or if you’re visiting around lunch/dinner pay a visit to Beekman Ale House for a meal and drink, which was also decorated with spooky decor.

From here, you can walk to historic and popular sites like Sleepy Hollow Cemetery and Phillipsburg Manor as well in under 5 minutes. 

You can walk down to the waterfront and enjoy the trail and views along the Hudson River as well as visit the Sleepy Hollow Lighthouse.

• Sleepy Hollow Cemetery & Old Dutch Reformed Church

Address: 540 N Broadway, Sleepy Hollow

An iconic place to visit in Sleepy Hollow at Halloween is the Sleepy Hollow Cemetery and Old Dutch Reformed Church, which plays a pivotal role in the setting of Washington Irving’s, The Legend of Sleepy Hollow . 

While the Old Dutch Reformed Church has its own burying ground in the churchyard and the Sleepy Hollow Cemetery are technically two different sites, they are easy to combine together as you can easily access one from the other.

The Old Dutch Reformed Church, also known as The Old Dutch Chruch of Sleepy Hollow, is a 17th-century stone church and was in Irving’s 1820 legendary tale which is also one of the oldest buildings in the state! Irving used the cemetery not only as the location where the Headless Horseman would start his nightly ride in his short story, but he also used the names from some of the gravesites here for his characters including Brom Bones and Katrina Van Tassel, whose gravestones you can visit.

After visiting the old churchyard, you can visit the gravesite of Washington Irving, which is technically a part of the Sleepy Hollow Cemetery. There are signs that will lead you to his family plot and gravesite which is helpful and makes it easy to find.

Other notable figures buried in Sleepy Hollow Cemetery include figures throughout American history like William Rockefeller, Andrew Carnegie, and Walter Chrysler to name a few. The cemetery itself is pretty large, so after visiting the sites around the Old Dutch Reformed Church, if your car is nearby you can explore the rest by driving through the cemetery (unless you’re up for a walk).

Be sure to check out the beautiful wooden bridges over the Pocantico River, which resemble what perhaps Irving imagined being the bridge in his short story, as the actual site of the Headless Horseman Bridge (marked with a sign) on Broadway is a more modern bridge that can handle automobile traffic and not reflective of what perhaps the area looked like when Iriving was inspired by in the 1800s. 

The graveyard is open to the public from 8:00 AM to 4:30 PM so be sure to plan your visit around these hours.

• Explore Tarrytown

Neighboring Sleepy Hollow is Tarrytown, which are less than a mile a part from one another. The Village of Tarrytown is charming and much like Sleepy Hollow at Halloween, the area has all kinds of spooky decor and you’ll spot several nods to the Headless Horseman and Irving’s characters from his classic tale.

Be sure to take a lap down Main Street (off of Broadway) where you can find plenty of opportunities to shop and dine along with catch a show at Tarrytown Music Hall, a historic theater dating back to 1885. They offer shows, ghost tours of the Music Hall with a ‘master storyteller’ and all sorts of programming from plays, performances, and showings of classic films like Rocky Horror Picture Show .

Don’t miss out on some of the cool shops here either like The Swan’s House on Broadway featuring unique home goods combining a curated collection of vintage items and artisan pieces. Speaking of vintage goods, there is also a consignment store and antique store on Main Street worth taking a lap in as well.

If you want to enjoy a walk, make your way down to the Hudson Riverfront and enjoy the views at Pierson Park located right next to the Tarrytown train station.

The Great Jack O’Lantern Blaze

Address: 525 S Riverside Ave, Croton-On-Hudson

Halloween in Sleepy Hollow is famous, but in recent years The Great Jack O’Lantern Blaze event has become just as famous as the locations directly tied to the Legend of Sleepy Hollow in Irving’s story. Located at the Van Cortlandt Manor in Croton-On-Hudson, around a 20-minute drive north up the Hudson Valley from Sleepy Hollow is a truly remarkable and unique experience (welcoming of all ages) that you won’t want to miss during the Halloween season!

Blaze, as locals call it, is an immersive walk through over 7,000 hand-carved, illuminated jack o’lanterns! There are several different displays and art installations all made with these blazing pumpkins including a jack o’lantern constellation tunnel, the Headless Horseman and Ichabod, NYC landmarks recreated as pumpkins like the Statue of Liberty, and more all on the grounds of a historic 18th-century manor (that’s also decked out in Halloween decorations with a light show synched to music).

This event is so popular they now have a location in Long Island too. The season to get tickets starts typically in mid-September and ends in November. You’ll need to reserve your tickets in advance , this is a hot item so you won’t want to miss out either, we advise booking your tickets as soon as you know the dates of your trip because they do sell out.

Visit Washington Irving’s Sunnyside Estate

Address: 3 W Sunnyside Ln, Irvington

Located in Irvington, New York (around a 10-minute drive from Sleepy Hollow) is the home of the legend himself, Washington Irving. His estate, known as Sunnyside, was where he built his countryside home near where he spent his childhood escaping the Yellow Fever Outbreak in New York City. His youthful years in the area would go on to inspire the setting in his short story, The Legend of Sleepy Hollow which he wrote while in England.

When Iriving returned stateside after becoming the first internationally celebrated American author, he built his dream countryside home here right along the Hudson River where visitors can see the creeping wisteria vines on the house that Irving planted himself over 200 years ago and retrace the footsteps of the father of American Literature.

During the months of September through November, visitors are able to tour the ‘Home of the Legend’  including the grounds surrounding his home and a tour inside the rooms on the first floor of his home. On the weekends during the month of October, visitors can enjoy Irving’s Legend performance in the evenings where a local master storyteller puts on a live-action performance of the story at the estate at dark for an audience.

For both of these events, you’ll need to book your tickets in advance as they do not sell them on-site.

• Tour the Armour-Stiner Octagon House

Address: 45 W Clinton Ave, Irvington

Another not to be missed attraction near Sleepy Hollow at Halloween time is touring the unique and pin Armour-Stiner Octagon House in Irvington. 

This unique octagon-shaped home was built by Paul J. Armour in the 1860s and was inspired by the octagonal homes that were a popular style in the pre-Civil war era. The home changed ownership in 1872 to Joesph Stiner, hence the name Armour Stiner and added the gorgeous dome that is said to be inspired by Donato Bramante’s 1502 Tempietto in Rome.

There are actually tours available throughout the year, but during the months of September through October concentrate on themes surrounding the mysteries and said paranormal activity in this home on their “Myths and Mysteries of The Octagon House” tour . Which is perfectly on theme for a spooktacular weekend getaway in Sleepy Hollow at Halloween time.

While the house does offer tours, it is a private residence and you are only able to visit by a guided tour booked in advance. The owner of the home, Joesph Pell Lombardi, is responsible for the restoration of the home to its 1872 appearance and furnishings. Lombardi is a world-renowned and famous real estate investor and preservationist who’s won awards and accolades for his preservation work including a 12th-century chateau in France.

Before or after your tour you can take a walk around the veranda or property to check out the matching pink carriage house (where his son/preservation partner resides) and greenhouse.

• Check Out Kykuit Rockefeller Estate

Address: 381 N Broadway, Sleepy Hollow (meeting location for tour)

Located in the Pocantico Hills above Tarrytown and Sleepy Hollow with sweeping views of the Hudson River and Valley is one of the most prestigious and historic estates in Westchester County. Kykuit, also known as the John D. Rockefeller Estate, was home to one of the wealthiest men in American history.

In 1913, John D. Rockefeller, the famous oil tycoon of Standard Oil, had the vision to build a grand countryside estate. Four generations of Rockefellers lived in this estate, which serves as a museum to the public with an impressive art collection on display for visitors on tours as well as beautiful gardens.

John D. Rockefeller’s grandson, Nelson Rockefeller (former Governor of New York and Vice President of the United States) curated and collected one of the greatest private collections of modern art in the country on the property including works from artists like Warhol to Picasso and are located in a private underground, basement gallery in addition to outdoor sculptures around the gardens.

To visit Kykuit (available May – November) you will need to purchase tour tickets in advance . There are three tour options ranging from one hour to three hours. Once you have your tickets, you will meet at the Phillipsburg Manor in Sleepy Hollow at the visitors center to check-in. They will provide a private shuttle up to the estate and return you back down here after your tour.

• Stop by the Union Church at Pocantico Hills

Address: 555 Bedford Rd, Tarrytown

Another Rockefeller artistic contribution to the area can be found at the Union Church of the Pocantico Hills, right near the entrance to Kykuit. If you’re visiting Sleepy Hollow around Halloween, this area is especially beautiful to drive to as the fall foliage is a sight to see.

Commissioned under Nelson Rockefeller as a memorial for his mother, the church is home to one of Henri Matisse’s last completed commissioned works in his lifetime, the Rose Window accompanied by nine stained glass windows by Marc Chagall.

Keep in mind this is an operating church, you’ll need to join a tour to visit and no photography is permitted inside the church. Tours are available on select dates (typically weekends) from May through November and you’ll want to purchase your tickets in advance.

If you can’t get your hand on tickets, you can drive past the church and see the Rose Window from the exterior of the church.

• Spend Time at Croton Gorge Park

Address: 35 Yorktown Rd, Croton-On-Hudson

If you’re visiting Sleepy Hollow by car, we highly encourage you to explore a little. Before visiting The Great Jack O’Lantern Blaze in Croton-On-Hudson, we recommend stopping by Croton Gorge Park where you can take a walk around the base of the New Croton Dam and the pretty man-made waterfall here.

There are trails and areas to picnic too, but we came mostly for the views. The New Croton Dam is impressive as when it was completed in 1906, it was considered the tallest dam in the world. The waterfall here is picturesque and a fun stop to check out in the area.

Visit Rockefeller State Park Preserve 

Address: 125 Phelps Way, Pleasantville

Visiting Sleepy Hollow at Halloween means you’ll be visiting around all the beautiful fall foliage. If you’re looking for outdoor activities to enjoy or a place to enjoy a nice leisurely hike, visit the Rockefeller State Park Preserve in Mount Pleasant, nearby Sleepy Hollow, and the Pocantico Hills.

The park was a part of the Rockefeller estate and was donated to the State of New York in 1983 for the public to enjoy, although the Rockefellers were welcoming of the public using the land as a park as early as the 1970s.

There are several trails spanning 45 miles to enjoy  on the original crushed stone carriage roads that John D. Rockefeller and his son laid out themselves in the early 20th century, which are wide and easy to walk on not to mention there are wood and stone bridges crossing the Pocantico River and other streams as well as beautiful rock outcroppings, Swan Lake, and beautiful forest scenery to enjoy.

There are several easy trails to hike . You can park at the Rockefeller State Park Preserve parking lot ($6 per car at the pay machines).

• Wander Around Untermyer Gardens Conservancy

Address: 945 N Broadway, Yonkers

Located in Yonkers in Westchester County, this is a great stop if you’re heading back to New York City after your weekend in Sleepy Hollow. Located along the Hudson River at the former site of the estate “Greystone,” are the grand gardens added to the now-demolished estate by Samuel Untermyer.

Untermyer Gardens Conservancy is now a public park, donated by Samuel Untermyer, hence the name. The gardens were a part of his vision for his countryside estate that he purchased, located on a steep parcel of land overlooking the Hudson River and New Jersey Palisades. 

Untermyer was a successful corporate lawyer in New York City turned civic leader, he wanted to build a grand garden that rivaled the gardens found at Kykuit, the Rockefeller estate nearby. At the time of their construction, the garden was considered one of the finest in the country.

The park is completely free to visit and a must if you’re in the area. Some of the features of the beautifully restored park include the Temple of Love, a rock and water garden with cascading waterfalls and a majestic view from the top, the Walled Garden which was designed and inspired by Indo-Persian gardens, and the long staircase from the Walled Garden to the Overlook with incredible views of the Hudson River.

Where to Eat in Sleepy Hollow at Halloween Time

Goosefeather.

Address: 49 E Sunnyside Ln, Tarrytown

Not to be missed during your weekend in Sleepy Hollow is the weekend brunch available at Goosefeather, a Cantonese restaurant located in the 1840s historic property at Tarrytown House Estate on Hudson, also a hotel in the area. 

James Beard nominated Chef Dale brings the flavors of Hong Kong here to the Hudson Valley with an innovative menu that even has nods from Michelin. Chef Dale also has made several television appearances including Top Chef, Chopped, Knife Fight, Beat Bobby Flay, and is the host of Tastemade’s All Up in My Grill.

In addition to great Cantonese-inspired dishes, there are several incredible brunch items to try, we highly recommend trying the Kung Pao Chicken and Mochi Waffles along with dumplings from their smaller plate options. We were also impressed with the Roasted Mushroom and Coconut Grits, which was a perfect combination of savory and sweet combining the flavors of umami butter, pomegranate seeds, and a six-minute egg along with the mushrooms and coconut grits. It was definitely not something we try to do at home, but Chef Dale has really created a stand-out dish with these flavors complimenting each other beautifully.

In addition to an impressive brunch menu, Goosefeather is open for dinner. Also, the space is absolutely beautiful too.

Brunch is available on the weekends starting at 11 AM, you’ll want to make a reservation.

Horsefeathers

94 N Broadway, Tarrytown

Located in the heart of Tarrytown is one of the best stops for lunch or dinner during the season of Halloween in Sleepy Hollow. Horsefeathers has an old tavern ambiance and is decked out with Halloween decor including a nice list of pumpkin beers, ales, ciders, and other fun ‘spooky’ drinks to add to your spooktacular weekend in Sleepy Hollow.

They serve up classic American pub fare, we highly recommend the burgers here paired with a pumpkin-flavored beverage or cocktail of your choice.

This is a very popular spooky season stop because of all of the festive decor and they do not take reservations. We recommend getting here a little early to put your name in as for parties with more than two had a lengthier wait time. We were able to get a seat at the bar without too much of a wait. 

Beekman Ale House

Address: 92 Beekman Ave, Sleepy Hollow

For a great lunch or dinner option in Sleepy Hollow, check out Beekman Ale House, a pub setting with great beer and drinks on draft plus pizza! What we liked about this spot is that it wasn’t too crazy, even during Halloween in Sleepy Hollow and they even have festive decorations.

We stuck with ordering a pizza paired with beer on draft, which was a great choice. They serve up Neopolitan-style pizza with a crispy crust plus a bunch of great shareable options like meatballs and fried mozzarella triangles.

Horseman Bagels

Address: 276 N Broadway, Sleepy Hollow

If you’re looking for a quick bite to eat in the morning during your weekend in Sleepy Hollow be sure to visit Horseman Bagels, which shares a space with Carvel, the classic ice cream spot serving up sweet treats.

What’s nice is that this location is directly across from the Sleepy Hollow clock and ‘official welcome’ to the town that’s outfitted with a spooky pumpkin man for Halloween season! You can easily grab a bagel and walk downtown.  right 

EATalia on Hudson

Address: 385 S Riverside Ave, Croton-On-Hudson (PERMANENTLY CLOSED AS OF 2023)

If you’re looking for somewhere to grab dinner before heading to Van Cortlandt Manor for The Great Jack O’Lantern Blaze, this is a great stop. Give yourself extra time, this is not a fast-service type of place but their pasta dishes are excellent.

If you order from the specials menu, be sure to ask the price to avoid any confusion on the bill later. We recommend giving yourself at least 75-90 minutes here so you can plan accordingly. Blaze is just up the road and because this is one of the most popular Halloween season attractions, you’ll also want to plan for a small window of time to sit and wait to park in a queue of cars – it wasn’t too long but we gave ourselves ample time to arrive thankfully.

Bread and Brine

Address: 19 Main St, Hastings-On-Hudson

An excellent spot for lunch or dinner in Hastings-On-Hudson, this New England-focused restaurant serves up incredible dishes inspired by the North East Atlantic coast including lobster rolls, a raw bar, and other great dishes like a whole branzino.

Do yourself a favor and after lunch take a lap around Hastings-On-Hudson, there are a few cute shops including a great record store, Clockwork Records and a cute antique shop on the corner of Main and Warburton, Suburban Renewal. 

Drive (or walk) down to MacEachron Waterfront Park for waterfront views and you can also see the skyline in the distance down the Hudson River.

Where to Stay During Your Sleepy Hollow Halloween Weekend: Tarrytown House Estate

For your weekend in Sleepy Hollow at Halloween, one of the best options for lodging and where to stay are the historic grounds of the Tarrytown House Estate . A popular wedding venue too, this hotel is situated on 26-acres with gorgeous 19th-century mansions including the Carriage House and Cottage, Biddle Mansion, and King Mansion.

The King Mansion is also the location of Goosefeather restaurant, which is a must during your Sleepy Hollow weekend trip. In addition to being a gorgeous property, the location is also excellent as you’re just a short drive to both Tarrytown and Sleepy Hollow making it a really great base for exploring all the stops in Westchester County featured in this guide.

The hotel rooms are inside a contemporary building between the historic properties. Enjoy your morning coffee walking around the property or cozy up by the firepits in the evening. There is an outdoor pool and indoor pool, sauna, racquetball, and tennis courts.

The property is really beautiful and reminded us of our stay in a historic property in Ireland . For the season of Halloween in Sleepy Hollow you’ll want to secure your reservation in advance, especially on the weekends as many weddings use the property as a venue and the rooms can book up quickly. Book here.

Getting to Sleepy Hollow & Westchester

Getting to Sleepy Hollow (and the nearby villages) from New York City couldn’t be easier as the Metro-North Railroad Hudson Line has several stops along the Hudson Valley including an express service between Grand Central Terminal in NYC and Tarrytown (which takes around 35-min).

You can easily take the train from many stops included on this weekend getaway to the Sleepy Hollow area including stops at Hastings-On-Hudson, Tarrytown, Sleepy Hollow, and Croton-On-Hudson, you will just need to plan your schedule to the train time tables .

From Penn Station, you can also use the Amtrak train to get to Metro-North’s Croton-Harmon Station.

Also, some of the local hotels have a shuttle service they offer to and from the train station making it possible to do this trip without a car if you don’t have one or don’t want to rent a car.

We prefer renting a car or driving so you have more flexibility, not to mention the drives here around fall are stunning because of the fall foliage.

You also have the option for taking the train up to Tarrytown or flying into Westchester County Airport (HPN) in White Plains and then renting a car once you’re here. There are even rental car options in Tarrytown and you can also use Zipcar in the area.

Tips for Visiting Sleepy Hollow at Halloween

Halloween time at Sleepy Hollow and the surrounding areas is the most popular time to visit. There are so many Halloween-focused attractions plus the North East is popular this time of year for leaf peepers. 

With that in mind here are a few tips to make sure you’re prepared:

• Parking can be competitive in the villages, have quarters on you for parking meters (they also have options to pay online) and be prepared that you may have to circle the downtown areas during peak times to find a spot. Or park a little further away and walk into where you’re going.
• Be sure to check any restaurants that you want to visit for reservations. Not all, like Horsefeathers, takes reservations in advance. If you’re visiting on the weekend and you didn’t get a reservation, schedule time in to wait for a table.
• Most attractions in the area require advance tickets and reservations. Be sure to look up all attractions you want to visit to secure your tickets in advance, especially for popular spots like The Great Jack O’Lantern Blaze, Washington Irving’s Sunnyside, and Kykuit. These places will not let you buy tickets on-site and often sell out.

Things to do in Sleepy Hollow at Halloween (Post Summary):

• The Great Jack O’Lantern Blaze
• Visit Washington Irving’s Sunnyside Estate
• Visit Rockefeller State Park Preserve
• Have Brunch at Goosefeather
• Have a Meal at Horsefeathers
• Stop at Beekman Ale House for a Meal
• Have a Bagel from Horseman Bagels
• Dinner at EATalia on Hudson
• Enjoy Lunch at Bread and Brine

No, you do not need tickets to visit Sleepy Hollow as it’s a town, but if you are hoping to do specific attractions or tours those may require tickets.

Yes, Sleepy Hollow, NY is worth visiting for its historical charm, ties to Washington Irving’s “The Legend of Sleepy Hollow,” scenic Hudson River views, and seasonal events like Halloween festivities.

Sleepy Hollow, NY celebrates Halloween with the Great Jack O’Lantern Blaze, an elaborate display of thousands of intricately carved pumpkins, creating a mesmerizing and magical experience for visitors.

Yes, Sleepy Hollow is worth visiting during Halloween for its renowned Great Jack O’Lantern Blaze nearby and spooky ambiance, plus the town is decorated for Halloween!

Enjoyed this guide to how to spend a spooktacular weekend in Sleepy Hollow at Halloween? Bookmark for later or share the love below on Pinterest!

For more spooky season destinations check out our guide to all the best things to do in Salem , which is not too far of a journey away and also check out our favorite places to visit in New York in fall !

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You Can Only Experience These Things In Sleepy Hollow During Halloween

The home of Ichabod Crane and the Headless Horseman is a great spot for fall festivities, with these Halloween experiences found in Sleepy Hollow.

Read update

There Are More Fun Things To Experience In Sleepy Hollow This Fall!

• Lyndhurst After Dark: Experience the eerie beauty of the historic castle at night during Sleepy Hollow's annual Lyndhurst After Dark. Guided tours in candlelight reveal the property's paranormal activity. Perfect for all ages.
• Sleepy Hollow Cemetery Tours: Explore the spooky Sleepy Hollow Cemetery, a must-visit during Halloween. Day and night tours are available, with the nighttime lantern tour providing an extra touch of Halloween vibes (not recommended for kids).
• The Great Jack O'Lantern Blaze: Join one of the largest Halloween events in the area at The Great Jack O'Lantern Blaze. With over 7,000 hand-carved jack-o'-lanterns, atmospheric lighting, and sound effects, it's a family-friendly event not to be missed.

Along the eastern shore of the Hudson River and a mere 25 miles north of New York City lies the little village of Sleepy Hollow . This small community remains a modern-day household name because of Washington Irving's frightening classic "The Legend of Sleepy Hollow," which tells the story of Ichabod Crane and his unfortunate run-in with a headless horseman. This, of course, means that Sleepy Hollow, to this day, makes for a great place to celebrate Halloween in New York as the village inspired Irving for obvious reasons with its gloomy atmosphere and historic buildings like its Old Dutch Church. Here are some Halloween festivities one can only find in Sleepy Hollow.

UPDATE: 2023/09/29 17:33 EST BY NOAH STAATS

This article has been refreshed with new things to do in Sleepy Hollow this fall and expanded information for each existing activity. This Upper New York town comes alive during Halloween, bringing spooks, scares, and plenty of memory-making opportunities to vacationers. Have fun!

11 Lyndhurst After Dark

• October 19th-22nd, 26th-29th, 2023
• Tickets: $20-$40 plus additional service fees

Something spooky to do this Halloween season in Sleepy Hollow is check out the city's annual ' ‎Lyndhurst After Dark ' celebration, bringing the season to full fruition for residents and locals. This event is when people are allowed to tour the historic castle at night, with guided tours through the gorgeous complex draped in candlelight. This will be a bit eerie, as the property is known to have paranormal activity through the evenings. Luckily, there won't be people jumping out and scaring you, so this is okay for younger people and children. Lyndhurst Mansion is an iconic Upstate New York tourist destination, so why not see it in its glory at night?

This only happens during the Halloween season!

10 Sleepy Hollow Cemetery Tours

• Cemetery tours throughout Sleepy Hollow are in abundance during Halloween.

Exploring a spooky cemetery should be considered a staple in all Halloween celebrations, and Sleepy Hollow Cemetery provides a perfect place for this. A variety of both day and night tours are offered here, which vary in length and content. Those looking for full-on Halloween vibes should opt for the nighttime lantern tour, but be aware that it is not kid-friendly, and tour organizers request not to bring minors.

9 The Great Jack O'Lantern Blaze

• This celebration is family-friendly, boasting over 7,000 jack-o'lanterns.

A fantastic family-friendly option is one of the largest Halloween events in the area, the Great Jack O'Lantern Blaze. This event showcases over 7,000 hand-carved jack o'lanterns throughout its expansive grounds, which tie it all together with a scary soundtrack and atmospheric lighting and sound effects.

Related: Some Of The Best Places To See Grand Jack-'o-Lantern Displays Are Right In The US

8 Sleepy Hollow Street Fair

• This is a lively Halloween-themed market in town.

The Sleepy Hollow Tarrytown Chamber of Commerce hosts an annual Sleepy Hollow Street Fair, which turns Beekman Avenue into a lively Halloween-themed market (with a few things dedicated to the upcoming holidays thrown in). It takes place on the second week of October every year, and this year it will fall on Saturday, October 8th. This event helps transform the streets into Halloween as other festivities like parades, hayrides, and live music are in full force.

7 Tarrytown Halloween Parade

• This is a festival in the next-door town of Tarrytown, New York.

The vibrantly festive Tarrytown Halloween Parade, which has four times been named "Best of Westchester," typically begins at Patriot's Park and ends on Main Street. This parade which is a fabulous mixture of fun and macabre, makes its way across town until its finishing point, where festivities continue with a block party of food and live DJ sets.

6 Armour-Stiner Octagon House Myths And Mysteries Tour

• This is a guided tour and storytelling opportunity in town (focuses on the architecture and history of the area).

The domed landmark built in the 1860s, often referred to as the Octagon House, has been the subject of rumors of the supernatural throughout its entire history, including its residents' personal accounts of ghost encounters. Every October, the doors open for guests to take a tour to admire the architecture while hearing the unsettling details of the home's paranormal past.

5 Irving's Legend

• This is a story-telling attraction based on Washington Irving's "The Legend of Sleepy Hollow."

What would Halloween in Sleepy Hollow be without a recounting of Washington Irving's "The Legend of Sleepy Hollow"? Johnathan Kruk is hailed as a master storyteller who has been featured in The TODAY Show and Travel Channel, and here he provides hauntingly dramatic performances telling the story of the headless horseman among other local tales like The Wailing Woman in White and Mother Hulda, the Witch of the American Revolution.

4 Tarrytown Music Hall Ghost Tours

• This famed music hall is haunted, which becomes more apparent during the Halloween season.

This tour brings visitors through the Tarrytown Music Hall, built in 1885, in which some of history's most wealthy families, like the Rockefellers and Vanderbilts, would visit the venue for opulent balls, concerts, and other events. Famed storyteller Johnathan Kruk guides the way through this historical building that has endured depressions, wars, and sociopolitical events. It is part of the Haunted History Trail of New York and has been visited by the Gotham Paranormal Research Society.

3 Tour Washington Irving's Home

• Washington Irving's Home is a great fall activity for those interested in history.

Families with a deep interest in the story this town is famous for would love this daytime tour of Washington Irving's estate. Visitors can tour the home, learn about the origins of Washington Irving's classic story, and also see some artwork inspired by it. Additionally, guests have the opportunity to view never-before-seen treasures from the Historic Hudson Valley collection and participate in Headless Horseman arts and crafts.

Related: Studies Show This State Has The Biggest Halloween Vibe

2 Hulda's Night In Rockefeller State Park

• Hulda's Night brings guests through an eerie outdoor adventure in the Rockefeller State Park Preserve.

Hulda's Night takes visitors into an eerie outdoor setting at Rockefeller State Park Preserve, surrounded by the dark forest only with lanterns to light the way. This experience takes guests on a journey, including a lone storyteller recounting local legends around a fire, hearing the woes of a pastor of the Old Dutch Church in 1775 regarding witches and war in times past, and ends with a meeting with Hulda herself in the spot where her hut was rumored to be nearly 250 years ago.

1 Haunted Hayride

• Haunted Hayride in Sleepy Hollow is one of the top-rated Halloween events in town.

The Haunted Hayride is perhaps the best experience happening in Sleepy Hollow during this time of year for those looking to strike a little Halloween fear into their heart. The ride carries passengers through the gloom of Sleepy Hollow, over an old wooden bridge, and past the iconic Old Dutch Church as they can only wonder what awaits them out there in the dark. Hay rides will take place on October 21st and 22nd, with block parties at the starting point to entertain guests until it is time for departure. Tickets are on sale now and tend to sell out, so act quickly.

• New York State

19 fun things to do in Sleepy Hollow, NY (that you’ll love!)

• Posted by by Elle-Rose
• Updated: September 20, 2023
• 8 minute read

Are you looking for things to do in Sleepy Hollow, New York? Keep reading for my recommendations!

If you’re looking for things to do in Sleepy Hollow, then you’ve come to the right place!

Sleepy Hollow in New York is a great place to visit for a weekend out of the city.

A place that’s always appealed to Halloween fans, Sleepy Hollow is an excellent place to visit during the spooky season.

However, though Sleepy Hollow caters superbly to the Halloween crowd, it’s a fantastic place to visit year-round.

With festivals, awesome landmarks, and seasonal attractions that travelers will enjoy no matter their age, as there are so many things to do in Sleepy Hollow!

It’s no surprise that Sleepy Hollow often finds itself inundated with out-of-towners. 

Now, if you’re looking for the low-down on activities in Sleepy Hollow, New York, then look no further for we’ve sourced some of the coolest things to do in the area so that you don’t have to.

Sleepy Hollow Farmers Market

First on my list of things to do in Sleepy Hollow, New York, it’s the Farmer’s Market!

If you love a good Farmers Market, then you’re in luck.

With weekend farmers’ markets commonplace in Sleepy Hollow, it’s one of the best things to do in the area if you fancy living like a local.

Whether you want to pick up fresh meat, bread, flowers, or dairy products, you’ll find the freshest produce here.

There’s often live music featured at these markets, so you can truly make a day of it!

The best one in the area is probably Tarrytown’s and Sleepy Hollow’s weekly farmers market, so make sure you stop by. 

Read more about New York State: The Ultimate Guide to Jamestown, NY

Have dinner in a castle

Next on our list of things to do in Sleepy Hollow, it’s a special dinner!

If you’re looking for something romantic and impressive to do in Sleepy Hollow… this might tick all the boxes!

Equus is a restaurant located inside the Castle Hotel and Spa, and it’s a fancy restaurant with amazing food and even better views.

If you’re looking for a date idea in Sleepy Hollow, this is a great option!

Phillipsburg Manor

Philipsburg Manor is next on our list of things to do in Sleepy Hollow.

If you want to explore Sleepy Hollow’s historical side, then be sure to swing by the historic Phillipsburg Manor.

Once a thriving farming, milling, and trading center, it was owned by a family of Anglo-Dutch merchants.

An excellent place to learn about 18 th -century colonial life, it’s one of Sleepy Hollow’s most historic spots.

New York according to both locals and tourists, this manor just had to make it onto our list!

If you happen to be visiting in October, the manor transforms on select evenings.

Becoming a haunted attraction during the month, you’ll have the opportunity to experience some top scares and excellent costumes whilst walking through the historic property!

Read more about New York State: 17 Beautiful and Scenic Towns in Upstate New York

Headless Horseman Monument

Next on my list of things to do in Sleepy Hollow, New York, it’s the spooky Headless Horseman Monument.

If you’ve read The Legend of Sleepy Hollow, then you won’t want to miss the Headless Horseman Monument.

One of the top attractions in Sleepy Hollow, for literature fans, this headstone monument depicts the famous scene in the story where the menacing horseman appears.

This monument is located at Phillipsburg Manor, so it’s a great idea to pay it a visit alongside your trip to the manor itself.

Make sure you bring your camera along for this one, as it’s a truly memorable photo spot!

Read more about New York State: 7 reasons you should visit mystical Lily Dale, NY

Kykuit is the next suggestion on my list. One of America’s most famous private residences, Kykuit: The Rockefeller Estate is a great way to spend the day in Sleepy Hollow.

Once home to the renowned oil tycoon John D. Rockefeller in the late 1800s, this amazing six-story stone house is a transportive step back in time.

Read more about New York State: The Ultimate Guide to The Finger Lakes, NY

Visitors can take guided tours of the property and hear stories about the Rockefeller family as they make their way round the property!

The Great Jack O’Lantern Blaze

Next on my list of things to do in Sleepy Hollow, New York, it’s one for the autumn months.

During the fall months, The Great Jack O’Lantern Blaze is a must-visit for those passing through Sleepy Hollow.

An amazing night-time display of carved pumpkins that take on various themes, it’s truly a sight to behold.

If you’re a fan of Halloween, be sure to book early, as tickets always sell out during peak weekends.

With this festival, you will truly feel like you’ve been dropped into Halloween Town (shoutout to the Nightmare Before Christmas fans amongst you!) because this is the perfect choice for things to do in Sleepy Hollow for you!

Though this isn’t technically in Sleepy Hollow (you’ll need to drive around 20 minutes to reach Croton-on-Hudson).

Read more spooky travel inspiration: 14 spooky abandoned places in Indiana

Visit the Armour-Stiner (Octagon) House

Next on my list of things to do in Sleepy Hollow, New York it’s the Armour-Stiner (Octagon) House is one of the most unique and eye-catching houses in the USA.

Yes, that’s a big statement, but wait until you see it, we think you’ll agree.

The Octagon House was built in the 1860s by Paul J. Armour, a New York City financier, and it’s really something special – it’s one-of-a-kind and it’s a must-see for anyone obsessed with ‘haunted-style’ houses.

This is something you won’t want to miss! This looks like one of those houses you’d see in a ghost / horror movie, and it’s a must-see when you’re in the Sleepy Hollow.

Watch the video below for a closer look at this amazing building…

Read more spooky travel inspiration: The 8 spookiest ghost towns in Missouri

The Old Croton Aqueduct

Another one of the top things to do in Sleepy Hollow, New York for history buffs is a visit to the Old Croton Aqueduct.

Touted as New York’s first water system, it now functions as a 26-mile walking trail that crosses through both Tarrytown and Sleepy Hollow.

Offering stunning views and a great glimpse into both villages, it’s a great choice for nature lovers too. 

Take a stroll around Tarrytown

Next on our list of things to do in Sleepy Hollow, it’s Tarrytown.

Tarrytown is right next door to Sleepy Hollow (literally you can walk from one to the other) and it’s a lovely scenic, historic town that you can stroll around.

On a summer’s day, it’s a lovely town to wander through and dip in and out of local stores.

Read more spooky travel ideas: Top 10 spooky abandoned places in New York

Order up a beer flight

If you love your beer and trying new brews – then taking a beer flight at the Bridge View Tavern is a great idea.

A beer flight is basically a chance to try a variety of beer (in small measures) and sample lots of the local beer talent.

The beer flight at the Bridge View Tavern is really well-known and a popular choice for visitors, and the perfect way to end a day of sightseeing too.

Sleepy Hollow Cemetery

Another spooky thing to do in Sleepy Hollow, New York is taking a trip to the Sleepy Hollow Cemetery.

Though we don’t recommend going after dark if you’re easily scared, the Sleepy Hollow Cemetery is an excellent attraction.

Tours are offered during the day that focus on Washington Irving and The Legend of Sleepy Hollow.

However, if you’re brave, why not hop on one of the tours that operate after dark? With names like “Murder and Mayhem”, proceed with caution!

We jest of course… But this is definitely one of the best things to do in Sleepy Hollow during Halloween and spooky season!

Read more about New York State: Top 15 things to do in Saratoga Springs, NY

Old Dutch Church of Sleepy Hollow

Old Dutch Church of Sleepy Hollow is the amazing stone church and adjoining burial ground that’s featured in Washington Irving’s story.

If you like history, then this is a great option for things to do in Sleepy Hollow, New York.

An atmospheric place to get to grips with The Legend of Sleepy Hollow, it’s well worth visiting and I think you’ll be fascinated by the place.

Though the cemetery is probably the main attraction here, the adjoining church is certainly worth a look!

Lyndhurst Castle

Who doesn’t love a castle? If you’re looking to see where some of your favorite vampire shows were filmed, then make sure you book a guided tour of Lyndhurst Castle.

For film and movie buffs this is a must-do for things to do in Sleepy Hollow, New York.

With a spooky exterior that’s got some great gothic flair, if you’re looking to indulge your inner architecture nerd, this is the place.

Trust us, this place is stunning. 

Spend a day on the river

Sleepy Hollow is right on the river (the Hudson river in case you’re wondering!) so it’s a great chance to do some river-based activities such as boating, fishing, paddle-boarding, kayaking, etc.

Getting out on the river (especially during the spring and summer) is a nice break from the more spooky things on this list, and it’s a chance to enjoy the great outdoors and the beautiful scenery!

Head out during sunrise or sunset for super gorgeous views.

Go antique shopping

You’d expect somewhere like Sleepy Hollow, New York to be popular with antiques hunters.

So antique hunting is next on my list of things to do in Sleepy Hollow, New York.

There’s something about the history of this place that means antiques stores seem to have popped up in and around the area.

There are quite a few to choose from – so if you’re set on doing a bit of antique shopping, then Sleepy Hollow is a pretty perfect place to do it.

You never know what you might find, and that’s definitely half the fun. I always like having a bit of a contest with my husband or friends, to see who can find the ‘weirdest’ item.

Or maybe the most haunted item!

Here are some of my top picks for antique shopping in Sleepy Hollow:

• Belkind Bigi
• Canfin Gallery
• Michael Christopher Antiques
• Carol Master Antiques
• Pretty Funny Vintage Antiques & Curious Goods
• Cherry Door Thrift Shop

Rockefeller State Park Preserve

The Rockefeller State Park Reserve is our next suggestion for things to do in Sleepy Hollow.

This huge park is comprised of 1,400 acres, so it’s the perfect place to explore and experience the great outdoor!

In the summer it’s perfect for hiking, running, bird watching, fishing, picnicking, horseback riding, carriage driving, photography, painting, and geocaching (park permit required).

You name it – there is SO MUCH you can do in this part of Sleepy Hollow!

With plenty of spots for a lovely picnic, it’s a great choice for that long-awaited family day out. 

Listen to some jazz music

Next up, on our list of things to do in Sleepy Hollow, it’s listening to some jazz music.

If you’re a music fan (and specifically into jazz) then you’re going to love the Jazz Forum , (located at 1 Dixon Lane, Tarrytown).

It’s a venue known for amazing music and jazz, and it’s constantly hosting amazing performers and putting on incredible shows.

It’s an intimate venue (only 100 people!) so it’s a really special music experience to have during your time in Sleepy Hollow.

You’ll find the headline jazz artists on Fridays and Saturdays, and celebrated Brazilian groups on Sundays.

It’s definitely worth a visit, and you’ll love it, especially if you fancy a night out!

Read more about New York State: 12 things to do in Tupper Lake, NY

Enjoy some theatre

Next on my list of things to do in Sleepy Hollow, New York, it’s the theater!

The local theatre venue for Sleepy Hollow is the Tarrytown Music Hall online box office .

You’ll find a load of different theatre performances at Tarrytown Music Hall, and there’s a big mix of talent and performers to choose from.

If you’re really set on a specific kind of performance, it’s a great idea to check out their website (linked above) to see the listing s and schedule ahead of your trip.

You can (very handily) but tickets through the online box office, or in person at the physical box office.

Headless Horseman Bridge

This famous bridge was written about many times (and used in movies) so it’s a must-see for anyone visiting Sleepy Hollow because of the literary roots!

We couldn’t really write a list of things to do in Sleepy Hollow without mentioning this local spot.

It’s a classic photo opportunity in the town, and you have to grab at least one selfie with it.

Hopefully this list has been useful!

There’s so much to do in Sleepy Hollow, so make sure you cram in as many of these suggestions as possible during your time there!

Hopefully this list of things to do in Sleepy Hollow, New York has been useful and you’ve got plenty of ideas for your trip!

Elle-Rose is the owner and editor of The World and Then Some! She has been a professional travel writer for over 12 years, writing for many different publications, including this one. Elle-Rose is a city break expert, and she specializes in popular locations such as NYC, London, Las Vegas and Dubai, regularly visiting to stay on top of new attractions, restaurants and hotels. Elle-Rose is super active on TikTok (@theworldandthensome), and loves filming video content in the cities she visits - so go and say hello!

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Visit Sleepy Hollow

Where the Legend Lives

• Christ Episcopal Church
• David Rockefeller Creative Arts Center at Pocantico
• Headless Horseman Bridge
• Headless Horseman Statue
• Historical Society
• Legend Landmarks

Spring Crafts at Lyndhurst

• Octagon House
• Old Croton Aqueduct Trail
• Old Dutch Church
• The Pinkster Festival
• Rockefeller State Park Preserve 

Cemetery Song

• Sleepy Hollow Cemetery Tours
• The Hill – Stories from Spoon River
• Sleepy Hollow Lighthouse
• Union Church of Pocantico Hills
• Events Calendar
• Sleepy Hollow Music Festival
• Tarrytown Music Hall Shows

Tarrytown Street Fair

• Halloween in Sleepy Hollow Country
• Farmers Markets
• Sleepy Hollow Souvenirs
• Lunch and Dinner
• Coffee & Tea
• Motels and Budget
• Inns and Bed & Breakfasts
• Sleepy Hollow Country
• How Charles Dickens Stole Christmas
• Movies Made Here

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Calendar of Events

4 events, 28, irvington farmers market.

Enjoy live music, river views and a laid-back setting at this small-town Sunday market showcasing the best of what the Hudson Valley has to offer. In season, there is fresh local produce, seafood and meats, cheese, pickles, prepared foods and baked goods. The market is just a short distance from Washington Irving’s home Sunnyside. Look …

The Original Knickerbocker Tour

The Original Knickerbocker: Washington Irving & “The Legend of Sleepy Hollow”. Meet the father of the American short story on this one-hour tour of Sleepy Hollow Cemetery! Learn all about Washington Irving, his impact on American Literature and the enduring appeal of “The Legend of Sleepy Hollow”, which recently celebrated its Bicentennial. Best of all, …

Classic Daytime Cemetery Tour

Soak up the beauty of this 175-year old cemetery while your guide regales you with stories of the fascinating people resting here in peace. This two-hour daytime walk is the perfect way "to have a colloquy among the tombs" as Washington Irving, famous author of "The Legend of Sleepy Hollow", did himself back in 1849. You'll …

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0 events, 30, 0 events, 1, rickie lee jones.

Rickie Lee Jones is an American musician, storyteller and two-time Grammy winner who has been inspiring pop culture for decades, beginning with her star-making self-titled debut, followed by the seminal Pirates. Named the “premiere song-stylist and songwriter of her generation” by The New Yorker, and “The Duchess of Coolsville” by Time magazine, Jones released her …

3 events, 3

The Spring Craft Show by ArtRider at Lyndhurst returns from May 5th through May 7th with 200 craftspeople and makers! Shop for one-of-a-kind gifts for Mother’s Day, Father’s Day, graduations, weddings, or just for yourself! Visitors can spend the day with family and friends shopping for original fashions, accessories, jewelry, home décor, furniture, photography, and …

Kykuit Tours

A majestic paradise with sweeping river views. See the Hudson Valley’s top cultural attraction! Built between 1906 and 1913, Kykuit was home to four generations of the Rockefeller family, beginning with the philanthropist John D. Rockefeller, founder of Standard Oil. His business acumen made him, in his day, the richest man in America. Now a …

Kevin Nealon

Kevin Nealon is an Emmy and SAG-nominated actor and comedian who sets himself apart from other comedic performers with his unique sense of humor, dry wit and likable demeanor. Nealon is best known for his nine-year stint as a cast member of NBC’s Saturday Night Live, and received critical acclaim for his role in the …

7 events, 4

6 events, 5, 0 events, 6, 0 events, 7, 0 events, 8, rodrigo y gabriela.

Grammy Award winning duo Rodrigo y Gabriela grew up on an eclectic mix of classic rock, heavymetal and flamenco, a rare alchemy of influences that still informs their work today. Not long after the dissolution of their first band, the two musicians set off with their acoustic guitars and ended up in Ireland, where they …

2 events, 10

Three figures stand in the lamplit darkness, their voices rising: an old woman, bent but strong and steel-eyed; a woman in the prime of life – a leader, a creator, a mother; and a young girl, full of curiosity and intelligence. Their song is haunting but joyful. As they sing, others begin to emerge from …

7 events, 11

5 events, 12, 0 events, 13, 0 events, 14, 0 events, 15, 1 event, 16, krishna das benefit concert for tibetan home of hope.

oin Krishna Das and friends for an evening of sacred kirtan music to benefit the Tibetan Home of Hope. The event is co-hosted by the Kirtan Wallah Foundation. Krishna Das is an American vocalist known for his performances of kirtan, a Hindu devotional music. Since 1996 Krishna Das has released sixteen music albums, numerous videos, …

1 event, 17

7 events, 18, sleepy hollow 150th anniversary car show.

This event offers a delightful blend of nostalgia and respect for Sleepy Hollow's automotive heritage, featuring an impressive array of classic vehicles that have left an indelible mark on the village's identity. Alongside classic, antique, and muscle cars, families can enjoy food trucks, music, and a bouncy castle. Rain date: May 19th. Automobile manufacturing was …

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0 events, 20, 0 events, 21, 0 events, 22, 0 events, 23, 2 events, 24, the machine performs pink floyd.

The Machine has forged a 30+ year reputation of extending the musical legacy of Pink Floyd. The New York-based quartet performs a diverse mix of The Floyd's extensive 16-album repertoire, complete with faithful renditions of popular hits as well as obscure gems. With stellar musicianship and passionate delivery, The Machine explores collective improvisation rivaling that …

7 events, 25

Tash farmers market.

Stop by TaSH, Tarrytown’s and Sleepy Hollow’s weekly farmers market, for fresh Hudson Valley produce, meat, bread, cut flowers, dairy products, preserves, wine, and beer. There are weekly live music performances, children’s events as well as ongoing educational activities and programs. Don’t miss the weekly free samplings! Well behaved dogs are welcome, provided your pooch is …

The Pinkster Festival

Join Philipsburg Manor for a day filled with art, poetry, live music, dance, and storytelling that celebrates and commemorates the region’s African American history and culture. Hear a spoken word performance, dance to the beat of African kora, observe an artist in process, participate in a call-and-response song, and more. Brought to the New World …

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1 event, 27, 0 events, 28, 2 events, 31.

A master lyricist and satirical storyteller, John Hiatt delivers songs filled with tales of redemption, relationships and surrendering on his own terms. Hiatt's finest album is 1987's Bring the Family; other catalog highlights include the pop and rock of 1983's Riding with the King, the rough-hewn blues-rock of 2008's Same Old Man, and 2021's Leftover …

9 events, 1

Rockwood ramble 10k.

Starting and finishing in historic Rockwood Hall, the annual Rockwood Ramble 10K is a favorite. Scenic Hudson River views greet runners before the course veers into the woods. The wide carriage roads provide the perfect setting for experienced trail runners and first timers. Say goodbye to traffic, pavement and noise and hello to the Preserve! …

The Sleepy Hollow Tarrytown Chamber of Commerce’s annual Tarrytown Street Fair takes place this year on Sunday, June 4th. Main Street transforms into an outdoor market with food, music, local retailers, arts & crafts, souvenirs and more! Explore more local shopping at Tarrytown's and Sleepy Hollow's galleries, gift shops and antique stores. Rain date: Sunday, June 2, …

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There’s something for everyone in Sleepy Hollow Country —farmers markets, live music, street fairs, historic homes, hiking trails, kayaking and boating on the Hudson River. Halloween season brings even more for the whole family—haunted hayrides, blazing pumpkins, costumed 10K run, Halloween parade, and of course, the Headless Horseman! For the latest on Fall events, visit our guide to Halloween in Sleepy Hollow .

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How to Spend a Weekend Exploring Sleepy Hollow, New York's Stately Manors, Historic Cemeteries, and Stylish Restaurants

By Juliet Izon

All products featured on Condé Nast Traveler are independently selected by our editors. However, when you buy something through our retail links, we may earn an affiliate commission.

It’s that time of year when we’re all in search of a bit of fright and colorful foliage mixed in with our fun, and one of our favorite weekend trips from Manhattan has all of that in spades: Sleepy Hollow, New York. While this lower Hudson Valley village is famous for being the real-life setting of Washington Irving’s short story The Legend of Sleepy Hollow , which was also a 1999 movie, there’s far more to explore here than just historical landmarks (though there are plenty of those as well). And there's plenty to see beyond the popular fall season, whether you want modern international fare, or exhilarating outdoor activities like hiking and biking. Here's our guide to this quaint upstate New York town, plus what else there is to discover nearby.

Getting to Sleepy Hollow NY

Traveling to Sleepy Hollow can be accomplished via a few options. From New York City, the drive time is about an hour and 15 minutes (though can be much more during rush hour). You can also hop on the Metro-North Railroad Hudson Line from Grand Central Station; the express train to nearby Tarrytown station is only about 35 minutes, and there’s also a local train to the village’s Philipse Manor station. If you’re coming from farther afield, the closest airport is Westchester County Airport, located about a 30-minute-drive away in White Plains, New York.

Kykuit Estate is the former home of philanthropist John D. Rockefeller.

What to do: Historic homes and quiet hikes

New York’s Hudson Valley is filled with elegant historic homes, charming Main Streets, and scenic hiking, biking, and strolling routes. But even for the area, Sleepy Hollow and its neighboring towns of Tarrytown and Irvington boast an outsized number of all of these.

In Sleepy Hollow proper, historic sites are the biggest draw. Fans of the spooky will certainly want to visit Sleepy Hollow Cemetery , which is the final resting place of a wide range of famed figures, including Washington Irving, Andrew Carnegie, and Elizabeth Arden. Just remember it’s still a working burial ground, so it’s important to be respectful. Philipsburg Manor is a fascinating look back in time: In the 1750s, the estate was run by a community of two dozen enslaved individuals of African descent and featured a bustling trading complex and mill, all of which that you can learn about on a visit. Perhaps unsurprisingly, the most visited spot in town is the Headless Horseman statue , created by local artist Linda Perlmutter. And finally, one of the most famous mansions in the state is here: Kykuit , the former home of philanthropist John D. Rockefeller, the founder of Standard Oil, and is a short drive from the Rockefeller State Park Preserve. The estate’s Classic Tour, at over two hours long, gives you an excellent overview of this impressive manse.

Nearby Irvington, however, is actually home to Washington Irving’s estate, Sunnyside . The charming and rambling home is on the banks of the Hudson River and offers guided tours on the weekends from May to September. And one of Westchester’s most architecturally unique homes is also in town: The Armour-Stiner Octagon House , As you can probably guess, it’s an eight-sided house that is the only fully-domed octagonal residence in the world. Guided tours are available from April to December (we recommend the Halloween tour to learn all about the mysteries of the home). From there, you can head to The Irvington Woods , a quiet preserve with over 40 miles of hiking, biking, and running trails.

In Tarrytown, one of the most visited sites is Lyndhurst , also known at the Jay Gould estate; the elegant mansion is one of the finest examples of Gothic Revival architecture in the United States. The house can be explored through multiple themed tours, or you can wander the grounds along the banks of the Hudson on your own. After, you can stroll Scenic Hudson’s RiverWalk Park , a gorgeous riverside esplanade with views of the Manhattan skyline.

Chinese food dishes at Goosefeather

Where to eat for modern Chinese and Indian cuisine, farm-to-table plates, and classic barbecue

The Hudson Valley boasts some of New York state’s most famed farms, so it’s no surprise that this suburban area punches well above its weight when it comes to restaurants.

In Tarrytown, Chef Dale Talde ’s modern Chinese food at Goosefeather has gained enough acclaim that it’s even become destination-dining for New York City folk. Another popular stop in town is Mint Premium Foods , a Mediterranean spot that is both a gourmet market and casual restaurant. Some of Westchester’s best brisket and pulled pork can be found at Pik Nik BBQ , where they smoke their meats daily. And of course, Blue Hill at Stone Barns , the temple to farm-to-table cuisine, is just north of the center of town.

Over in Irvington, the most famed spot may be the modern Greek menu at MP Taverna , run by chef Michael Psilakis of Iron Chef America fame. Other noteworthy restaurants include Chutney Masala for stellar Northern Indian food, Sambal for Thai and Malay, and Red Hat on the River for its dreamy water views. And to top off your meal with a sweet treat, make a beeline for Red Barn Bakery, whose 100 percent organic menu includes apple-salted caramel crumb pie, savory cheddar-kale scones, and flourless chocolate cake.

Steph Koyfman

Alex Erdekian

Laura Walsh

Jamie Spain

Tarrytown House Estate

Where to stay in Sleepy Hollow, New York

The move here is to post up at one of the area’s charming boutique hotels. Tarrytown House Estate (also the home of Goosefeather restaurant), consists of 212 rooms and 10 Georgian-style suites, some housed in the historic King Mansion. The 26-acre estate also contains a pool, tennis court, and plenty of lawn games. Another nearby option, also housed in a historic building is Castle Hotel and Spa , a smaller property with 31 recently renovated guest rooms. And while the spa is currently closed, you can still reserve private Swedish massage sessions in your room.

A little further afield, about 30 minutes from Sleepy Hollow, is Bedford Post Inn . We think it’s worth the distance to spend a night or two at this Relais & Chateaux property, which has only eight guest rooms, all with Frette linens and many with working fireplaces. There are also three restaurants which are worth the drive alone: casual The Barn with southern French cuisine, The Terrace’s seasonal food from its wood-burning oven, and the elegant contemporary American menu at The Farmhouse.

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How to Explore Sleepy Hollow, the Real-Life Halloween Legend

One of things that surprises most people about Sleepy Hollow, is finding out that it is a real place. For a name so shrouded in folklore and tales of headless horsemen told around firesides, it may seem like the creation of a gothic writer’s imagination, but Sleepy Hollow is in fact a small quaint village to be found just north of New York City. And there is no finer time to explore the area than the month of October – leaf peeping season – when people come from the world over to visit the place where Washington Irving set the Legend of Sleepy Hollow. So without further ado, here is our handy guide to some of the delights to be found when visiting Sleepy Hollow Country .

“There is a little valley or rather lap of land among high hills, which is one of the quietest places in the whole world. A small brook glides through it, with just murmur enough to lull one to repose….From the listless repose of the place, and the peculiar character of its inhabitants, who are descendants from the original Dutch settlers, this sequestered glen has long been known by the name of Sleepy Hollow…The whole neighbourhood abounds with local tales, haunted spots, and twilight superstitions.” – The Legend Of Sleepy Hollow, Washington Irving.

One of the best aspects of visiting Sleepy Hollow Country is the actual journey of getting there: starting at Manhattan’s magnificent Grand Central Terminal, a Metro North train will transport you from the metropolis to the lair of the Headless Horseman in just over half an hour, via one of America’s most picturesque train journeys that hugs the banks of the Hudson River. Our destination is the railway station of Tarrytown, about twenty five miles north of the City, for the legend of Sleepy Hollow is a really a story of two neighbouring villages, Tarrytown and Sleepy Hollow. 

“In the bosom of one of those spacious coves which indent the eastern shore of the Hudson, at that broad expansion of the river denominated by the ancient Dutch navigators the Tappan Zee, there lies a small market town or rural port, which by some is called Greensburgh, but which is more generally and properly known by the name of Tarry Town…..Not far from this village, perhaps about two miles, there is a little valley or rather lap of land among high hills, which is one of the quietest places in the whole world. A small brook glides through it, with just murmur enough to lull one to repose.” – Washington Irving’s, The Legend of Sleepy Hollow.

Make the short journey up a winding street from Tarrytown station and you’ll find yourself on the charming main street of the village where Washington Irving made his home. The spirit of Irving still looms large over the area: you’ll find banks, apartment buildings and schools all named in honour of the “first American man of letters”.

If you spot the local ambulance driving by, you’ll see its side is painted with a full length depiction of the Headless Horseman throwing fiery pumpkin heads at Ichabod Crane; at Sleepy Hollow High School, the football mascot is routinely voted as the scariest in America – it is a real life horse ridden by a headless rider, charging down the touchline.

On a misty morning when the fog rolls in from the Hudson River, it still seems just as Irving wrote two hundred years ago that, “a drowsy, dreamy influence seems to hang over the land, and to pervade the very atmosphere.”

The Old Dutch Church and Burying Ground

One of the best places to visit is the Old Dutch Church of Sleepy Hollow. Head northwards along Broadway and you’ll pass a giant spectacular sculpture of the Headless Horseman and a millpond bridge of the atmospheric Phillipsburg Manor, a 17th century Dutch Colonial manor house and farm before arriving at a beautiful small stone church perched atop a hill overlooking the old Albany Post Road.

Founded in 1685 by Dutch settlers it is one of the oldest in New York State. Before you step inside the church, notice the different coloured bricks that make up the arch around the door frame; these were the actual bricks used as ballast in the ships that brought the Dutch colonists across the Atlantic and up the Hudson River over three hundred years ago. The church bell, which still peals to bring people to services was also brought from 17th century Holland along with a heavy, dark wood communion table. Far from just a historic landmark, the church is still active and thriving and family oriented. Services are still held here in the summer months and at Christmas, the congregation warmed by an old cast iron stove. The rest of the year, the Dutch Reformed Church meets at an 1830s church on Broadway in Tarrytown. 

Washington Irving regularly visited the Old Dutch Church and it would inspire his most famous tale of a Hessian soldier from the Revolutionary War, who’s head was carried away by a cannon ball that haunts Sleepy Hollow. 

“Indeed, certain of the most authentic historians of those parts, who have been careful in collecting and collating the floating facts concerning this spectre, allege that the body of the trooper, having been buried in the church-yard, the ghost rides forth to the scene of battle in nightly quest of his head; and that the rushing speed with which he sometimes passes along the Hollow, like a midnight blast, is owing to his being belated, and in a hurry to get back to the church-yard before daybreak.” – The Legend of Sleepy Hollow, Washington Irving

Irving was thirty six years old, writing part time whilst working mostly as a lawyer, when he wrote The Sketch Book of Geoffrey Canon, Gent in 1819.  The collection of stories included the Legend of Sleepy Hollow and Rip Van Winkle, peculiar tales that swiftly captured the public’s imagination, and garnering Irving the reputation as the first true writer of American fiction.

Outside the church you will find an old burial ground, with many of the 17th century tombstones written in the native Dutch of the settlers. Amongst them you’ll find a certain Katrina Van Tassell and Brom Bones (Abraham Martling) who would feature prominently in the Legend of Sleepy Hollow. 

There is also an actual bridge with an historic marker indicating that “The Headless Horseman Bridge described by Irving in the Legend of Sleepy Hollow formerly spanned this stream at this spot”. The actual wooden bridge has long since gone, but was actually a bit further upstream inside our next stop, Sleepy Hollow Cemetery .

Found right next to the old Dutch Church burying ground but a separate entity entirely, the cemetery is the final resting place of Washington Irving himself. The beautiful and still active cemetery was built during the fashion for landscaped garden cemeteries in the 1800s, and you’ll find notables such as Andrew Carnegie and William Rockefeller buried amidst the elaborate mausoleums.

The cemetery also offers excellent tours such as champagne cocktails whilst peeking inside the mausoleums, and night time visits lit by kerosene lantern. You’ll also find a quaint wooden bridge across the stream that it is far easier to imagine Ichabod Crane racing across.

Ghost Tours of a 19th Century Music Hall

Back in Tarrytown, located near the top of Main Street you will find the Tarrytown Music Hall. A beautiful red brick theatre built in 1885 with Queen Anne flourishes from the same architectural firm that designed Macy’s grand department store in Herald Square and the Grand Central Palace. One of the first theatres in America to show motion pictures, the exquisite building also hosted lavish balls and entertainments for Tarrytown’s millionaire residents, such as the Rockefellers, Vanderbilts and the Goulds, some of the wealthiest families in the United States. Today, the Music Hall is still open as a concert venue, and offers nightly ghost tours during the month of October. There’s nothing quite as enchanting as the faded gilt and plush glamour of an old theatre dating back to the 19th century, and is the perfect setting to explore the secrets of old Tarrytown Music Hall. 

The Mysterious Octagon House

The Armor Stiner house could be our most favourite home in all of America. Built during the 19th century fashion for eight sided houses, this peculiar octagonal shaped home can be found just south of Tarrytown. Octagon Houses were dreamt up by a leading Victorian phrenologist, and the Armor Stiner is perhaps the most beautiful remnant of the movement. From its lush gardens and beautifully painted eight sided porch, to an exquisitely decorated ‘Egyptian’ room topped with a magnificent dome resembling an ancient Roman temple, you can find out much more about the history of octagon houses and the Armor Stiner, in our behind-the-scenes visit and talk with its owners.

During October there is a special other-worldly delight of an exhibit and installation by Ryan Matthew Cohn, creator of the Oddities Flea Market . Part of the Armor Stiner’s season ‘Myths and Mysteries’ house tours, Cohn’s collection of peculiar antiques and ephemera are shown against the backdrop of one of America’s most unique and enchanting homes.

The Great Jack O’Lantern Blaze

Perhaps the most spectacular reason to visit Sleepy Hollow Country is the wildly magical Jack O’Lantern Blaze , where over 7,000 pumpkins have been breathtakingly carved, illuminated and built into every shape possible. Life sized working carousels spin alongside dinosaurs, the Headless Horseman bridge, and even an art gallery featuring pumpkin themed versions of grand masters. The Blaze can be found within the grounds of an 18th century estate, the Van Cortlandt Manor in nearby Croton, whose ancient timbers and buildings are lit only by the ghoulish glow of thousands upon thousands of pumpkins.

We caught up with professional pumpkin carver Jonas LG Karlsson, a Swedish artist living in Sleepy Hollow , to explore the captivating allure of one of Halloween’s most recognisable elements: the humble pumpkin.

“When I carve pumpkins…it is the same thing as when you stare at old wood finish, you suddenly can imagine a face or details in the pattern that almost come alive at you. That is how I do it with pumpkins. I begin by staring. It is quite effective most of the time….the process from start a finished pumpkin includes sketching, inking and lastly carving, so it can take much longer than most people think.” For Karlsson, the draw of living and working in Sleepy Hollow is palpable.

“My fascination for Sleepy Hollow is the mix of true history and literary legends and myths which you can see traces of here and there. I love Washington Irving’s legacy and the more I learn about his life and work the more I want to explore. It is just a special feeling knowing he walked the cobblestones on the same street as me.” 

Our favourite part of visiting the Blaze is to sip a pumpkin beer from the local Captain Lawrence Brewing Company and follow the pumpkin lit trail to a disused tavern built in 1750 by the banks of an old river crossing for the Albany Post Road back to Manhattan. As this ancient thoroughfare recedes into the distance as you can faintly hear the sound of approaching hooves on cobblestones of a horseman missing his head. 

Listen To The Legend of Sleepy Hollow Under The Stars

There can be no better place to listen to a live telling of the Legend of Sleepy Hollow than at the home of its author. When Washington came to Tarrytown to live, he did so in suitable style, moving into a 17th century stone cottage called Sunnyside that had once belonged to the Van Tassell family of Sleepy Hollow. Irving redesigned the house, giving it a wonderful appearance, part gothic fairytale andpart Dutch Colonial, covered in haunting looking wisteria. From this quaint cottage overlooking the Hudson River, Irving would host evening with his literary friends, and write in his study in what Harper’s Weekly descibed as ‘the best known and most cherished of all the dwellings in our land.” During October, this magical little cottage in the woods is host to a live retelling of the Legend of Sleepy Hollow performed by local master storyteller Jonathan Kruk. A captivating one man show in the grounds of Sunnyside, complete with an appearance of an actual headless Hessian horseman, the evening brings to mind old fashioned story telling around the fireplace.

Off The Beaten Path

When out exploring we always like to try and uncover the more peculiar, out of the way discoveries that perhaps don’t make it into regular guide books. Here are just a few things to keep your eyes peeled for when walking about Sleepy Hollow Country…

Passing mostly undisturbed behind the main through fare of Broadway is an old path. It cuts through people’s back gardens, parks, woodlands and grand mansions. What’s special about the path is what lies underneath – a 19th century aqueduct! A remarkable feat of engineering, it used gravity to bring water from Westchester County all the way down to midtown Manhattan. Today it is possible to walk the entire 40 plus miles of the Croton Aqueduct that will give you a unique glimpse into another side of Sleepy Hollow Country. You can find out more about this hidden gem when we set out to walk its distance.

Whilst the Old Dutch Church of Sleepy Hollow attracts the most visitors, another church in Tarrytown bears a slightly more personal bequest from Washington Irving that lives onto this day. Irving served as a vestryman at Christ Episcopal Church on South Broadway from 1848 until his passing. He planted ivy using cuttings he had taken from Abbotsford House in Scotland, the home of his close friend Sir Walter Scott, who had encouraged Irving to write the Sketchbook of Geoffrey, Gent. Wander over to the this still active church today, and you will see Sir Walter Scott’s living ivy today, adorning the church facade facing Broadway, via the hands of Washington Irving. The gothic grandeur of Lyndhurst looks like it would be more at home overlooking a Scottish loch than the banks of the Hudson.

Whilst the magnificent former home of railway robber baron Jay Gould, once one of the wealthiest men in America is well worthy of a taking a tour around, we’re particularly fans of two spots on the sweeping grounds. A short walk from the mansion is a beautifully preserved, old fashioned Wooden Bowling Alley we discovered when setting out to track down the last of these in America. Keep walking still and you’ll come across the abandoned ruins of an immense rose and orchid greenhouse, once the pride and joy of the lady of the mansion, Helen Gould. This estate greenhouse was at one time thought to be the largest and most state of the art greenhouse in America, but today it is a haunting, overgrown and rusted remnant of the Gilded Age.

Patriot’s Park and André’s Brook which runs through it marks the dividing line between Tarrytown and Sleepy Hollow. This beautifully landscaped park played host to a key event that swung the tide of the American Revolution. It was here early in the morning of September 23rd, 1780 that John André, a major in the British Army and head of its Secret Service in America was caught by three local men of Tarrytown in the park. He was carrying in his sock the plans on how to take the military stronghold of West Point on the Hudson River that had been handed to him by a disillusioned American general, Benedict Arnold, who commanded the fort.

Major André had been trying to escape through American lines to Manhattan in plain clothes, when three Tarrytowner’s, John Paulding, Isaac Van Wart and David Williams caught him. André was hung as a spy by the order of George Washington, and a memorial was put in Patriot’s Park, known as the Captor’s Monument featuring a statue of John Paulding, bearing the inscription, “Here in 1780 three honest militiamen arrested Major John André Adgt-Gen. British Army, disguised, preventing disaster to American cause.” Host to a farmer’s market on Saturday morning, make sure to sit by the brook that still runs through the park: for this was where Ichabod Crane first encountered the Headless Horseman!

Spooky Sips

If you’re wondering how Tarrytown got its rather unusual name, Washington Irving provides the answer in the Legend of Sleepy Hollow:

“We are told, in former days by the good housewives of the adjacent county, from the inveterate propensity of their husbands to linger about the village tavern on market days.”

After a long day’s exploring Sleepy Hollow Country there are fortunately many taverns in which one may still tarry and linger a while with a restorative. Here are our favourites…

First port of call is Horsefeathers on North Broadway. This cosy, family run tavern is lined with rich dark wooden panelling, snug booths, shelves filled with books, and old time black and white films on the televisions. It also happens to be wonderfully decorated for the autumn season!

Wander along Broadway and stop by the Tapp, named for the Tappan Zee Bridge that once spanned the Hudson between Tarrytown and Nyack. The bridge’s recent replacement was named after New York State Governor Mario Cuomo, but is still known by locals, many of whom you will find propped up against the friendly bar as the Tapp! Make your way down Main Street and enjoy and true taste of Cuba at the Cube Inn, with superb cocktails that transport you happily to Havana! On the other side of the street is the Set Back Inn, a village staple, sometimes boisterous, open late and an always friendly pitstop set back as the name implies from Tarrytown’s principal street. Over in Sleepy Hollow, we always like to drop in at the Beekman Ale House . It is a good sign you’re in a local neighbourhood spot when the bar is decorated with the helmet shields of all the local volunteer fire departments. The Ale House also happens to have the best pizza in town.

There is much more to explore in Sleepy Hollow Country with the autumn season filled with other spooky and historical events. The best place to find out more is at the excellent  Visitsleepyhollow.com website. The calendar in particular will be helpful to guide your path. 

And so we take our leave of Sleepy Hollow Country, where Ichabod Crane disappeared never to be seen again. Visit this October and you will find two charming small villages, Tarrytown and Sleepy Hollow, steeped as much in early American history as they are in spooky folklore. A place where just as Washington Irving wrote over two hundred years ago, “If ever I should wish for a retreat whither I might steal from the world and its distractions, and dream quietly away the remnant of a troubled life, I know of none more promising than this little valley.”

Written by Luke J Spencer , our gentleman explorer and resident of Sleepy Hollow.

From the archives.

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15 Spectacular Things To Do in Sleepy Hollow NY

“Certain it is, the place still continues under the sway of some witching power, that holds a spell over the minds of the good people, causing them to walk in a continual reverie. They are given to all kinds of marvelous beliefs, are subject to trances and visions, and frequently see strange sights, and hear music and voices in the air.” – The Legend of Sleepy Hollow

Sleepy Hollow, New York , yes as in that Sleepy Hollow, is a cozy village about an hour north of New York City in Westchester County. Originally named North Tarrytown, the residents voted in 1996 to officially change the town’s name to Sleepy Hollow as a means of uplifting the local economy. At the time, the New York Times noted that changing a town name is a rare occurrence. Even so, the village people made their wishes clear, and ever since, Sleepy Hollow has lived on. 

Tarrytown and Sleepy Hollow are both great names, and no matter what its called, it’s a town that’s full of history, amazing sights, family-friendly adventures, outdoor activities, and more. Here are 15 things to do in Sleepy Hollow NY that we know you’ll love.

LIVE THE LEGEND OF SLEEPY HOLLOW

Tarry Town was originally settled by the Dutch and was believed to be bewitched by those who lived there. Perhaps that’s why beloved early American author Washington Irving set his The Legend of Sleepy Hollow in that sleepy village.

Irving’s story goes that schoolmaster and local ghost story lover Ichabod Crane wants to win the hand of Katrina Van Tassel. However, Brom Bones also wishes to marry Katrina and sets out on a pranking spree against Ichabod to scare him out of town. That’s how the legend of the Headless Horseman became Ichabod’s living nightmare. 

When a town changes its name to reflect its place in fictional history, they’re obviously going to go all out. The Headless Horseman even makes an appearance on the homepage of Visit Sleepy Hollow . He’s basically the town mascot. It’s clear that visitors to the village will encounter their fair share of Irving’s version of the town, formerly known as Tarry. 

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WALK THE ROWS OF SLEEPY HOLLOW CEMETERY

Sleepy Hollow Cemetery has more than its fair share of permanent residents. According to the organization’s website, the cemetery houses nearly 50,000 interments. Guided tours are offered that share the stories of Washington Irving, his Headless Horseman and the lore of Sleepy Hollow.

Visitors can see the graves of John D. Rockefeller, Walter Crystler and Andrew Carnegie among others with stunning views of the Hudson River throughout.

It must be noted that visitors are only able to visit Irving’s grave during daytime tours or opening hours. 

STOP AT THE DUTCH REFORMED CHURCH

“Indeed, certain of the most authentic historians of those parts, who have been careful in collecting and collating the floating facts concerning this specter, allege that the body of the trooper, having been buried in the church-yard, the ghost rides forth to the scene of battle in nightly quest of his head; and that the rushing speed with which he sometimes passes along the Hollow, like a midnight blast, is owing to his being belated, and in a hurry to get back to the church-yard before daybreak.” – The Legend of Sleepy Hollow

Founded in 1685, the Old Dutch Church or Dutch Reformed Church is where Ichabod Crane believes the Headless Horseman originates from in Irving’s story. The church isn’t open for visitors much outside of October, likely because it is still an active congregation, and it is also not open after dark. 

CROSS THE HEADLESS HORSEMAN BRIDGE

It should come as no surprise that the wooden bridge Irving would have known in his lifetime (the late 18th and early 19th centuries) is long gone. According to Visit Sleepy Hollow, several iterations of the so-called Headless Horseman Bridge have existed since Irving’s life, and none really remain. Because that bridge doesn’t exist anymore in the same way, the visitor’s bureau suggests the rustic Cemetery Bridge for photos instead. 

Please note the Cemetery Bridge is frequently used for funerals or visitors of the cemetery, so do be respectful.

GRAB A SELFIE WITH THE HEADLESS HORSEMAN SCULPTURE

One of the town’s most visited spots is the Headless Horseman statue .

Located between the Dutch Church and Philipsburg Manor, the oxidized statue has become a must-see part of the town since it first came on the scene in 2006. (It debuted on Halloween in 2006, obviously!)

TOUR IRVING’S HOME

“The land of literature is a fairy land to those who view it at a distance, but, like all other landscapes, the charm fades on a nearer approach, and the thorns and briars become visible.” – Washington Irving

If you cannot get enough of Irving’s background and characters elsewhere in Sleepy Hollow, you need to check out his home Sunnyside . Sunnyside is part of the Philipsburg Estate (more on that below) along the Hudson River. Irving’s home looks like it is straight out of a novel, which makes sense given its former tenants. You can even see Irving’s office when visiting Sunnyside. 

VISIT FOR HALLOWEEN

Obviously Halloween is a big deal in Sleepy Hollow. The town goes all out for the spooky season with events like the Great Jack O’Lantern Blaze! The blaze involves over 7,000 illuminated jack-o-lanterns that are hand carved just for the occasion. 

Haunted hayrides, spooky tours and performances and even dramatic interpretations of Irving’s novel abound during the Halloween season. Sleepy Hollow does up the season as much as they can.  Visiting the city during October is truly one of the best things to do in Sleepy Hollow NY!

SEE THE BRONZE LADY (SLEEPY HOLLOW’S OTHER GHOST STORY)

Within the confines of Sleepy Hollow Cemetery, across from the grave of Civil War General Samuel Thomas, a giant bronze statue of a woman is said to be haunted. According to the legend , anyone who sits upon The Bronze Lady’s lap, jumps down and spins three times around before looking at her will be cursed. But her legends don’t stop there. 

Another legend says if you sit on her lap before peering into Thomas’ mausoleum door across the way, you’ll see a spirit. Others too say if you insult the statue you’ll get bad luck or touch her face and bring a curse upon yourself. No matter which of the legends you believe, it makes the somber looking statue a touch more menacing. 

SEE THE DUTCH-ORIGINATED TOWN BEYOND THE LEGEND

Given its proximity to the coast, it makes sense that the town now known as Sleepy Hollow has such a long history. Before it was colonized by the Dutch, the area belonged to the Weckquaesgeek tribe. The area’s history is vast and so are its offerings. There is more to Sleepy Hollow beyond the spooky horsemen, Ichabod and gothic tales. 

TOUR PHILIPSBURG MANOR

Open for visitors each year between May and November, the 18th century New York State historical site known as Philipsburg Manor was once a busy mill and trading center along the Pocantico River. Here, visitors learn not just about the estate itself, but the nearly two dozen enslaved people who worked and lived there. The reconstructed watermill also shows guests how they were able to grind grain in the 1700s. 

The Philipse family estate once included over 50,000 acres of land. A fitting amount of land for one of the area’s biggest businesses of the time. Now the estate lives on as a living-history museum focused on the enslaved people who made the business possible. (Historic Hudson Valley notes that the Philipse family was one of the largest slaveholding families in the North.) 

The manor was also part of Irving’s fictional Sleepy Hollow.

“Our man of letters, therefore, was peculiarly happy in the smiles of all the country’s damsels. How he would figure among them in the church-yard . . . or sauntering, with a whole bevy of them, along the banks of the adjacent mill-pond; while the more bashful country bumpkins hung sheepishly back, envying his superior elegance and address.” – The Legend of Sleepy Hollow

GRAB A PHOTO OF THE ARMOUR-STINER OCTAGON HOUSE

Not technically in Sleepy Hollow proper, the Armour-Stiner Octagon House can be found in Irvington, New York. It is the only known, fully domed octagonal residence — not only in the United States, but the world. It was modeled after Donato Bramante’s 1502 Tempietto in Rome. Built in the 19th century, the lavish home looks like it belongs in Alice in Wonderland more than in New York State.

The estate has been restored to its 1872 aesthetic in the American neo-Roman style, which was only popular for a short time during the 1800s. 

Guests can partake in a variety of tours around the property, from The Classic Tour which is offered year round, to seasonal tours, the Halloween tour, and even holiday tours, in addition to private tours of the home. 

HIKE ROCKEFELLER STATE PARK PRESERVE

Named for the famed Rockefeller family whose property houses the over 1770 acre Rockefeller State Park Preserve , the park is a quiet place to spend some time in Pleasantville, NY. The park is open all year from sunrise to sunset and is a favorite for walkers, joggers, bikers, and all kinds of outdoorsy activities. Here you can even marvel at the views once shared by the Rockefeller family from their beloved estate and 200+ room mansion. 

Here is also where you’ll find locations that lend themselves to Sleepy Hollow’s infamous reputation. Places like Spook Rock Trail and Witch’s Spring Trail, for instance. Spook Rock has its own legends behind it too.

According to Visit Sleepy Hollow, on quiet nights you may see dancing, ethereal maidens dancing around the rock or a celestial woman looking through the forest for the family she once lost. The legends stem from a longer ghost story detailed by the visitor’s bureau here . 

SEE THE SLEEPY HOLLOW LIGHTHOUSE

Known as the Sleepy Hollow Lighthouse , the Tarrytown Lighthouse, and Kingsland Point Lighthouse all in its lifetime, the lighthouse is still a place visitors love to see.

According to Visit Sleepy Hollow, it used to be half a mile away from shore but is now just a few feet from land. Tours are offered throughout the year by the village of Sleepy Hollow, otherwise you get an excellent view of the lighthouse from the Westchester Riverwalk.

SEE THE STAINED GLASS AT UNION CHURCH 

You might not be able to tell from the outside that the Union Church of Pocantico Hills is home to several masterpieces. The 1922 church houses the very last work by Henri Matisse, and several more by Marc Chagall, through a commission from John D. Rockefeller Sr.

The church’s Rose Window was Matisse’s last artwork before he died. Whereas Chagall created nine other stained glass windows for the church which are: The Good Samaritan, The Crucifixion, Joel, Elijah, Daniel, Cherubim, Ezekiel, Jeremiah and Isaiah. 

As the congregation is still active, tours are available outside of church activities. Tours of Union Church are arranged through Historic Hudson Valley. 

TOUR KYKUIT

There really is no visiting Hudson Valley without coming into contact with lots of spaces once owned by the Rockefeller family. One such location is known as Kykuit, the 1913 estate built by John D. Rockefeller Sr. Later Kykuit housed his son John D. Rockefeller Jr., before then being home to four time NY governor and later Vice President Nelson A. Rockefeller. 

Beyond the home’s exquisite interior design, the estate still houses the Rockefeller family’s impressive art collection. There are works by Andy Warhol, Alexander Calder, Louise Nevelson, David Smith, Pablo Picasso and Henry Moore to name a few.

Visitors can enjoy three different tours of the grounds, including the Selected Highlights Tour (90 minutes), the Classic tour (135 minutes), and the three-hour Grand Tour. Each tour provides guests with various sights around the grounds. The only one that includes everything, as well as extra time to enjoy the property, is the Grand Tour.

TASH FARMERS MARKET

Stop by TaSH , Tarrytown’s and Sleepy Hollow’s farmers market held at Patriots Park every Saturday from Memorial Day weekend through Thanksgiving.

You’ll love the Hudson Valley produce, bread, dairy products, wine and beer, meat, flowers, and so much more. You will also find live music, children’s events, and other activities and programs.

Enjoy free parking at John Paulding School, bring your leashed pet along, and make a visit here the perfect start to your Sleepy Hollow weekend.

TARRYTOWN MUSIC HALL

Built in 1885, Tarrytown Music Hall is not only a great place to catch a show, but a beautiful historic building that’s worth a visit all on its own.

The music hall is a great example of Queen Anne-style brickwork, and features Victorian and Art Deco styles on the inside. Guests can see a mix of performances here — from music and theater to films and comedy — and everything in between.

Tarrytown Music Hall is listed on the National Register of Historic Places.

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Assembly Bill A10058

Authorizes a residential parking system in the village of Sleepy Hollow in the county of Westchester

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Authorizes a residential parking system in the village of Sleepy Hollow in the county of Westchester.

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40 Facts About Elektrostal

Written by Lanette Mayes

Modified & Updated: 02 Mar 2024

Reviewed by Jessica Corbett

Elektrostal is a vibrant city located in the Moscow Oblast region of Russia. With a rich history, stunning architecture, and a thriving community, Elektrostal is a city that has much to offer. Whether you are a history buff, nature enthusiast, or simply curious about different cultures, Elektrostal is sure to captivate you.

This article will provide you with 40 fascinating facts about Elektrostal, giving you a better understanding of why this city is worth exploring. From its origins as an industrial hub to its modern-day charm, we will delve into the various aspects that make Elektrostal a unique and must-visit destination.

So, join us as we uncover the hidden treasures of Elektrostal and discover what makes this city a true gem in the heart of Russia.

Key Takeaways:

• Elektrostal, known as the “Motor City of Russia,” is a vibrant and growing city with a rich industrial history, offering diverse cultural experiences and a strong commitment to environmental sustainability.
• With its convenient location near Moscow, Elektrostal provides a picturesque landscape, vibrant nightlife, and a range of recreational activities, making it an ideal destination for residents and visitors alike.

Known as the “Motor City of Russia.”

Elektrostal, a city located in the Moscow Oblast region of Russia, earned the nickname “Motor City” due to its significant involvement in the automotive industry.

Home to the Elektrostal Metallurgical Plant.

Elektrostal is renowned for its metallurgical plant, which has been producing high-quality steel and alloys since its establishment in 1916.

Boasts a rich industrial heritage.

Elektrostal has a long history of industrial development, contributing to the growth and progress of the region.

Founded in 1916.

The city of Elektrostal was founded in 1916 as a result of the construction of the Elektrostal Metallurgical Plant.

Located approximately 50 kilometers east of Moscow.

Elektrostal is situated in close proximity to the Russian capital, making it easily accessible for both residents and visitors.

Known for its vibrant cultural scene.

Elektrostal is home to several cultural institutions, including museums, theaters, and art galleries that showcase the city’s rich artistic heritage.

A popular destination for nature lovers.

Surrounded by picturesque landscapes and forests, Elektrostal offers ample opportunities for outdoor activities such as hiking, camping, and birdwatching.

Hosts the annual Elektrostal City Day celebrations.

Every year, Elektrostal organizes festive events and activities to celebrate its founding, bringing together residents and visitors in a spirit of unity and joy.

Has a population of approximately 160,000 people.

Elektrostal is home to a diverse and vibrant community of around 160,000 residents, contributing to its dynamic atmosphere.

Boasts excellent education facilities.

The city is known for its well-established educational institutions, providing quality education to students of all ages.

A center for scientific research and innovation.

Elektrostal serves as an important hub for scientific research, particularly in the fields of metallurgy, materials science, and engineering.

Surrounded by picturesque lakes.

The city is blessed with numerous beautiful lakes, offering scenic views and recreational opportunities for locals and visitors alike.

Well-connected transportation system.

Elektrostal benefits from an efficient transportation network, including highways, railways, and public transportation options, ensuring convenient travel within and beyond the city.

Famous for its traditional Russian cuisine.

Food enthusiasts can indulge in authentic Russian dishes at numerous restaurants and cafes scattered throughout Elektrostal.

Home to notable architectural landmarks.

Elektrostal boasts impressive architecture, including the Church of the Transfiguration of the Lord and the Elektrostal Palace of Culture.

Offers a wide range of recreational facilities.

Residents and visitors can enjoy various recreational activities, such as sports complexes, swimming pools, and fitness centers, enhancing the overall quality of life.

Provides a high standard of healthcare.

Elektrostal is equipped with modern medical facilities, ensuring residents have access to quality healthcare services.

Home to the Elektrostal History Museum.

The Elektrostal History Museum showcases the city’s fascinating past through exhibitions and displays.

A hub for sports enthusiasts.

Elektrostal is passionate about sports, with numerous stadiums, arenas, and sports clubs offering opportunities for athletes and spectators.

Celebrates diverse cultural festivals.

Throughout the year, Elektrostal hosts a variety of cultural festivals, celebrating different ethnicities, traditions, and art forms.

Electric power played a significant role in its early development.

Elektrostal owes its name and initial growth to the establishment of electric power stations and the utilization of electricity in the industrial sector.

Boasts a thriving economy.

The city’s strong industrial base, coupled with its strategic location near Moscow, has contributed to Elektrostal’s prosperous economic status.

Houses the Elektrostal Drama Theater.

The Elektrostal Drama Theater is a cultural centerpiece, attracting theater enthusiasts from far and wide.

Popular destination for winter sports.

Elektrostal’s proximity to ski resorts and winter sport facilities makes it a favorite destination for skiing, snowboarding, and other winter activities.

Promotes environmental sustainability.

Elektrostal prioritizes environmental protection and sustainability, implementing initiatives to reduce pollution and preserve natural resources.

Home to renowned educational institutions.

Elektrostal is known for its prestigious schools and universities, offering a wide range of academic programs to students.

Committed to cultural preservation.

The city values its cultural heritage and takes active steps to preserve and promote traditional customs, crafts, and arts.

Hosts an annual International Film Festival.

The Elektrostal International Film Festival attracts filmmakers and cinema enthusiasts from around the world, showcasing a diverse range of films.

Encourages entrepreneurship and innovation.

Elektrostal supports aspiring entrepreneurs and fosters a culture of innovation, providing opportunities for startups and business development.

Offers a range of housing options.

Elektrostal provides diverse housing options, including apartments, houses, and residential complexes, catering to different lifestyles and budgets.

Home to notable sports teams.

Elektrostal is proud of its sports legacy, with several successful sports teams competing at regional and national levels.

Boasts a vibrant nightlife scene.

Residents and visitors can enjoy a lively nightlife in Elektrostal, with numerous bars, clubs, and entertainment venues.

Promotes cultural exchange and international relations.

Elektrostal actively engages in international partnerships, cultural exchanges, and diplomatic collaborations to foster global connections.

Surrounded by beautiful nature reserves.

Nearby nature reserves, such as the Barybino Forest and Luchinskoye Lake, offer opportunities for nature enthusiasts to explore and appreciate the region’s biodiversity.

Commemorates historical events.

The city pays tribute to significant historical events through memorials, monuments, and exhibitions, ensuring the preservation of collective memory.

Promotes sports and youth development.

Elektrostal invests in sports infrastructure and programs to encourage youth participation, health, and physical fitness.

Hosts annual cultural and artistic festivals.

Throughout the year, Elektrostal celebrates its cultural diversity through festivals dedicated to music, dance, art, and theater.

Provides a picturesque landscape for photography enthusiasts.

The city’s scenic beauty, architectural landmarks, and natural surroundings make it a paradise for photographers.

Connects to Moscow via a direct train line.

The convenient train connection between Elektrostal and Moscow makes commuting between the two cities effortless.

A city with a bright future.

Elektrostal continues to grow and develop, aiming to become a model city in terms of infrastructure, sustainability, and quality of life for its residents.

In conclusion, Elektrostal is a fascinating city with a rich history and a vibrant present. From its origins as a center of steel production to its modern-day status as a hub for education and industry, Elektrostal has plenty to offer both residents and visitors. With its beautiful parks, cultural attractions, and proximity to Moscow, there is no shortage of things to see and do in this dynamic city. Whether you’re interested in exploring its historical landmarks, enjoying outdoor activities, or immersing yourself in the local culture, Elektrostal has something for everyone. So, next time you find yourself in the Moscow region, don’t miss the opportunity to discover the hidden gems of Elektrostal.

Q: What is the population of Elektrostal?

A: As of the latest data, the population of Elektrostal is approximately XXXX.

Q: How far is Elektrostal from Moscow?

A: Elektrostal is located approximately XX kilometers away from Moscow.

Q: Are there any famous landmarks in Elektrostal?

A: Yes, Elektrostal is home to several notable landmarks, including XXXX and XXXX.

Q: What industries are prominent in Elektrostal?

A: Elektrostal is known for its steel production industry and is also a center for engineering and manufacturing.

Q: Are there any universities or educational institutions in Elektrostal?

A: Yes, Elektrostal is home to XXXX University and several other educational institutions.

Q: What are some popular outdoor activities in Elektrostal?

A: Elektrostal offers several outdoor activities, such as hiking, cycling, and picnicking in its beautiful parks.

Q: Is Elektrostal well-connected in terms of transportation?

A: Yes, Elektrostal has good transportation links, including trains and buses, making it easily accessible from nearby cities.

Q: Are there any annual events or festivals in Elektrostal?

A: Yes, Elektrostal hosts various events and festivals throughout the year, including XXXX and XXXX.

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