Updated August 2025

It’s that time of year again, it’s time to start planning those fall adventures! I’m a lover of all things fall and Halloween! Sleepy Hollow, New York, is an absolutely perfect fall day trip and a phenomenal Halloween destination! From the dramatic telling of The Legend Of Sleep Hollow to the Jack-O-Lantern Festival that happens each year, this charming small town is full of Halloween spirit! What should you do with One Day In Sleep Hollow?

When Should I Visit?

FALL! Sleepy Hollow is amazing in fall, and the entire town goes all out, complete with Headless Horsemen, Pumpkin Festivals, and decorations galore.

I’ve always loved The Legend of Sleepy Hollow (book, movie adaptations, and shows included). In case you are not familiar, Sleepy Hollow is the setting for Washington Irving’s The Legend of Sleepy Hollow.

Know Before You Go:

• The best time to go for fall color is usually the middle of October. You will not have any fall colors in September.
• It’s easiest to park in event parking and just walk the town. It’s a very walkable town.
• All of the normal Irving Halloween Attractions are canceled for 2020.
• In 2019, Philipsburg Manor was under construction and did not look at all as it looks in the photo above.
• Philipsburg Manor is closed for 2020 and I’m not sure if it is still under construction.
• Sleepy Hollow is usually incredibly busy in October but with everything canceled this year – it might just be the year to check it out!

The Legend of Sleepy Hollow

In case you’ve never heard of The Legend of Sleepy Hollow…

Washington Irving’s The Legend of Sleepy Hollow is set in 1790 and follows Ichabod Crane, who is described as “a scarecrow who had escaped his post, with a pointy snipe nose.” (Kruk) Ichabod was a schoolteacher and choirmaster who accepts the position in a small town in the Hudson Valley.

There is a small love triangle between Ichabod and one of the richest girls in town, Katrina Van Tassel. Now although Ichabod seems harmless, he has less than honorable intentions when it comes to Katrina. He wants to marry her for her money. His rival is Mr. Brom Bones, and while Ichabod is only after money, Brom is in love with Katrina. 

It’s a small town, so eventually, Ichabod hears rumors around the town of the legend of the Headless Horseman. As the legend goes…

The Headless Horseman

“The dominant spirit, however, that haunts this enchanted region and seems to be commander-in-chief of all the powers of the air is the apparition of a figure on horseback without a head. It is said by some to be the ghost of a Hessian trooper, whose head had been carried away by a cannon-ball in some nameless battle during the revolutionary war, and who is ever and anon seen by the country folk hurrying along in the gloom of night, as if on the wings of the wind.” (Irving 5)

Ichabod Crane is the superstitious type who believes these rumors (legend) and becomes paranoid and terrified that he will be the horseman’s next victim. 

Basically, at a town party, Ichabod dances with Katrina, but he begins to suspect that she is only using him to make Bones jealous. Serves him right! I’m pretty sure there is a song right about now in the Disney version. While walking home from the party, Ichabod is chased by the Headless Horseman and is never heard from or seen again. 

One Day In Sleepy Hollow

Can’t Miss Attractions

Old Dutch Church and Burying Ground

I know at this point you think I’m that creepy person hanging out in cemeteries! I promise I’m not. The Old Dutch Church and Burying Ground is the final resting place of Washington Irving (the writer of The Legend of Sleepy Hollow. You can usually take a guided lantern tour through the cemetery (this has been canceled for 2020). However, for those who flock to the cemetery hoping to find the actual people behind The Legend of Sleepy Hollow’s characters, I’ve got your back!

Old Dutch Church Of Sleepy Hollow| 430 Broadway, Sleepy Hollow, New York 10591

• If you are looking for inspiration for Katrina Van Tassel, it isn’t the similarly named Catriena van Tessel. While her name was borrowed for the story, the real inspiration was from Eleanor van Tassel Bush.

• Abraham “Brom” Bones can be found under the name Abraham Martling. 

• According to Irving, the Hessian Headless Horseman was buried in the churchyard. There is an unmarked field in the northeast corner of the cemetery where the outcasts were buried with no headstones.

And, of course, you can’t forget Washington Irving’s gravesite.

• Other legends surround Sleepy Hollow. There is a Bronze Lady statue in Sleepy Hollow Cemetery, and it is said if someone sits in her lap, knocks on her tomb, or kicks her in the shin, they will be plagued by nightmares for 2 weeks.

For other real inspirations of Washington Irving’s, The Legend of Sleepy Hollow, you can see the Philipsburg Manor, which was the inspiration for the Van Tassel’s house. 

Philipsburg Manor

The Philipsburg Manor is a living history museum where visitors can enter 1750. You can usually tour the manor house, explore the working gristmill, learn about the lives of the enslaved manor workers, visit the activity center, and hear the history of the manor. Unfortunately, it appears that the Manor itself is closed for 2020. However, you can see the Philipsburg Manor from across the pond and take photos. 

Philipsburg Manor| 381 N Broadway, Sleepy Hollow, New York 10591| Buy Tickets Here

Headless Horseman Bridge

You can easily walk, but it’s also possible to drive, and you may want to. This is one of the most popular sites in town, but many think it’s the original bridge. The bridge is over the river on the cemetery grounds. While it is not the original bridge, it is something you should see. 

• Insider tip: If you walk, hang out and wait for someone to drive over the bridge. If you drive at the perfect speed over the bridge, you can hear the hoofbeats of the Headless Horseman’s horse! The key is not to drive too slowly or quickly. There is a sweet spot right in the middle where it sounds exactly like hoofbeats! How awesome!

Headless Horseman Bridge| 430 Broadway, Sleepy Hollow, New York 10591 (On The Grounds Of Old Dutch Cemetary)

Sculpture of Headless Horseman

The sculpture of Irving’s Headless Horseman is just south of Old Dutch Church. Around 10 years ago, the village, formerly known as North Tarrytown, officially changed its name to Sleepy Hollow. The statue is made of laser-cut steel and is something to see!

Headless Horseman Sculpture| 420 N. Broadway, Sleepy Hollow, New York 10591

Headless Horseman Monument 

“Flee Ichabod, Flee!” This monument,built-inn 1974, depicts the famous scene from The Legend Of Sleepy Hollow where Ichabod flees while pursued by the Headless Horseman. 

Headless Horseman Monument| 381 North Broadway, Sleepy Hollow, NY 10591

Washington Irving’s Sunnyside

As you explore the romantic riverside cottage and landscape designed by America’s “Founding Father of Literature,” Washington Irving, you will be struck by how idyllic this spot truly is. Nestled along the banks of the Hudson River, the landscape of Irving’s beloved Sunnyside is charming and a must-visit destination for any fan of Sleepy Hollow.

Today you can hear about Irving’s storied past and how he came to be America’s first internationally famous author. His characters, from the Headless Horseman to Rip Van Winkle, and the legacy lives on at his fun and whimsical estate.

Sunnyside| 3 W Sunnyside Lane, Irvington, NY 10533| Buy Tickets Here

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Where To Eat In Sleepy Hollow

The Best Coffee: Coffee Lab Roasters 

• Where: 7 Main Street, Tarrytown, New York 10591 
• Hours: Mon-Sun – 6:45 am – 5 pm 
• Takeout Only at this time
  • The takeout menu is found here.

I always stop here on my way into Sleepy Hollow or if I need a quick pick-me-up before my drive home. It’s such a great coffee shop, and everything I’ve ever tried was delicious.

My Favorite: Bridge View Tavern

I highly recommend having lunch or dinner at the Bridge View Tavern before you leave Sleepy Hollow.

• Where: 226 Beekman Ave, Sleepy Hollow, New York 10591
• Hours: Daily 11:30 am – 10 pm 
• Outdoor & Limited Indoor Seating
• Curb-side Pickup (Call 914-332-0078 to order)
  • Click here to see the menu.

Rated number 1 of the 18 restaurant options in Sleepy Hollow by Trip Advisor, this little place has some seriously yummy food. I am admittedly easy to please when it comes to food, and I can recommend the North American Elk Burger, the Chipotle Bison Burger, the Wild Boar Chorizo Burger, and the Disco is Dead Fries (wild boar fries).

Tip:

Expect a wait if you are visiting Bridge View Tavern/Sleepy Hollow on a weekend in October. I figured it would be smart to go at a “weird” time, around 2-2:30. But everyone else had the same idea: the wait for a party of 2 was around 45 minutes, and a party of 5 was around an hour.

My advice is to make the best of it and check out their Beer Garden (this was added since my first visit to Sleepy Hollow). I know it sounds super basic, but try the Pumpkin Spice Sangria or a hot cider. I promise you won’t regret it! This place is worth the wait, so grab and drink and enjoy the autumn sunshine until your table is ready!

Fine Dining & Upscale Options

Blue Hill at Stone Barns ⭐⭐ (Michelin 2-Star)

• Where: 630 Bedford Rd, Tarrytown
• Hours: 5:30-9:30 PM from Monday through Saturday, Sunday = 11:30-2:30 and 5:30-9:30 PM
• This farm-to-table restaurant has retained its two Michelin stars and focuses on seasonal fare from 64 local farms, creating unique prix-fixe menus
• Reservations start around $298+ per person and book up months in advance Blue Hill at Stone Barns

Goosefeather

• Where: 49 East Sunnyside Lane, Tarrytown
• Hours: Monday-Thursday: 5PM-10PM, Friday: 5PM-10:30PM, Saturday: 11AM-2:30PM and 4PM-10:30PM, Sunday: 11AM-2:30PM and 4PM-8PM
• Chef Dale Talde’s Hong Kong-inspired restaurant infuses traditional Cantonese fare with seasonal Hudson Valley produce
• Find out more here

Casual Fine Dining

Sweet Grass Grill

• Where: 24 Main Street, Tarrytown, NY
• Hours: Lunch: Mon – Fri 11:30am-4pm, Brunch: Sat & Sun 10am-4pm, Dinner: Sun – Thurs 5pm-8:30pm,
  Fri-Sat 5pm-9:30pm
• Emphasizes local harvest with a regularly changing menu featuring local ingredients in a casual and rustic American setting
• Find out more here

International Cuisine

Hudson Farmer & the Fish

• Where: 11 River Street, Sleepy Hollow
• Hours: Monday Through Thursday: 12pm-8:30pm, Friday & Saturday: 12pm-9:30pm, Sunday: 12pm-8pm
• Waterfront restaurant with Hudson River views featuring seasonal specialties from their own farm, full raw bar, pizza, and seafood classics
• Find out more here

Croqueteria

• Where: 166 Cortlandt Street, Sleepy Hollow
• Hours: Wed-Sun 11 AM – 4 PM
• Soups, salads, sweet and savory croquettes, and “Home of the Real Cuban Sandwich”
• Find out more here

Great Casual Spots

The Sailhouse

• Where: Washington Irving Boat Club Marina, Tarrytown
• Hours: 11 AM to 10 PM most days
• Vibrant waterfront restaurant and bar with stunning Hudson River views, known for delicious food and friendly staff
• Find out more here

Grass Roots Kitchen

• Where: 124 Wildey Street, Tarrytown
• Hours: 9 AM to 8 PM
• “Fresh-casual” spot serving high-quality foods with options for vegan, gluten-free, and omnivores alike
• Find out more here

End Your Day At 

Rockwood Hall State Park/ Rockefeller Park

• Where: Rt. 9, Sleepy Hollow, New York 10591

Take a stroll and walk off dinner in Rockwood Hall State Park. The 2.1-mile loop trail follows carriage roads around the park, formerly the home of William Rockefeller, with panoramic views of the Hudson River. 

Sleep Hollow Fall Festivals/Attractions

Updated August 2025

There’s something for everyone in Sleepy Hollow in October: haunted hayrides, Gothic mansions, blazing pumpkins, live music, street fairs, a Halloween parade, and of course, the Headless Horseman!

The Great Jack-O-Lantern Blaze

• Select Nights Sept. 12 – Nov. 16, 2025
• Tickets start at $24
• Advanced Reservations Required – Buy Tickets HERE

The area’s biggest Halloween event features over 7,000 hand-carved, illuminated pumpkins. These jack-o-lanterns are set against the mysterious backdrop of Van Cortlandt Manor’s 18th-century buildings and riverside landscape.

Get ready for all new thrills at this year’s event! Spot iconic New York landmarks carved in pumpkins, then stroll the Pumpkin Promenade to catch fresh themed displays every week. Step right up for a big top adventure made entirely of jack o’lanterns, or follow the yellow brick road into a massive, emerald-hued storybook pumpkin dreamscape that’s wickedly fun. And don’t forget to swing by the Headless Horseman’s Hideaway, where you can sip spooky cocktails and brace yourself for haunting visits from the Horseman himself.

Irving’s Legend

• Sunnyside, 3 W Sunnyside Lane, Irvington, NY 10533
• Select Dates October 3 – Nov 1, 2025 – Fridays & Saturdays > Performances at 6, 7:30, 9pm
• Sundays & Monday > Performances at 5, 6:30pm
• Sunday, Oct. 12 > Performances at 6, 7:30, 9pm
• $45 per adult and $40 per child
• Advanced Reservations Required (Not Tickets Sold On Site) – Buy Tickets HERE

The Legend comes to life this fall at Washington Irving’s Sunnyside! Gather under the stars as master storyteller Jonathan Kruk weaves the timeless tale with the help of live music, spine-tingling sound effects, and a chilling visit from the Headless Horseman himself. With shadowy characters and an atmosphere straight out of the story, this seated outdoor performance is a spooky, family-friendly tradition you’ll want to experience year after year.

The Spirits of Sleepy Hollow Country

• Select Dates Oct 3 – Nov 1, 2025 – Fridays & Saturdays Performances > 2, 6, 7:30, 9:00pm
• Sundays & Monday Performances > 3:30, 5, 6:30pm
• Philipsburg Manor: 381 N Broadway, Sleepy Hollow, NY
• Recommended For Ages 10+ Only
• You can buy ticket here in advance.

Step into the supernatural at this one-of-a-kind magic show! Master illusionists conjure the spirits of Sleepy Hollow Country, Hulda, Major André, and even the Headless Horseman, in a spellbinding performance that blurs the line between trick and truth. Mysterious, chilling, and full of surprises, this all-original spectacle will leave you wondering what’s real…and what still lingers in the shadows.

Twilight Village At Sleepy Hollow

• Select Dates Oct 3 – Nov 1, 2025
• Oct 3-5, 10-13, 17-19 > First admission 6:30pm, last 9pm
  Oct 24-26, 31, Nov 1 > First admission 6pm, last 9pm
• Philipsburg Manor: 381 N Broadway, Sleepy Hollow, NY
• Good for all ages
• Adults: $30    Seniors & Young Adults: $29   Children: $25
• Make sure to buy tickets here in advance

As twilight envelops Philipsburg Manor, step into Twilight Village at Sleepy Hollow, where the spirit of Washington Irving’s famous tale comes alive in an immersive evening under the stars. Wander through a festive night market bursting with handmade curiosities and eerie keepsakes, sip on cocktails and mocktails, and munch on autumnal treats. Cross paths with wandering storytellers, groove to roving musicians spinning haunting melodies, and if you dare, clutch your phone tight for a face-to-face encounter with the Headless Horseman himself. This charming and slightly spooky celebration of folklore is a delightful Halloween tradition for all ages.

The Headless Horseman Files

• Select Dates Oct 3 – Nov 1, 2025
• Fridays > First admission 12pm, last 4:15pm
  Saturdays & Sundays & Monday > First admission 11am, last 4:15pm
• Philipsburg Manor: 381 N Broadway, Sleepy Hollow, NY
• Recommended for ages 8+ only
• Adults: $30    Seniors & Young Adults: $29   Children: $25
• Make sure to buy tickets here in advance

Step into the mystery at Philipsburg Manor with a 45-minute interactive walk that brings Washington Irving’s tale to life. Guided by lantern light, you’ll encounter colorful townsfolk – Hans Van Ripper, Katrina Van Tassel, Hulda the Witch, and Brom Bones, each with their own secrets about Ichabod Crane’s fate. But beware…the Headless Horseman may be closer than you think. Part whodunit, part live theater, this immersive adventure invites you to solve the mystery yourself in a spooky, family-friendly night you won’t forget.

Where To Stay In Sleepy Hollow

High End: Castle Hotel & Spa

• 400 Benedict Ave, Tarrytown, NY 10591
• 4 Star Hotel
• Rooms Around $399 A Night
• Find Out More HERE

Mid-Range: Tarrytown House Estate On The Hudson

• 49 E Sunnyside Ln, Tarrytown, NY 10591
• (914) 591-8200
• Rooms between $96-$130 On Average
• Find Out More HERE

Mid-Range: The Sleepy Hollow Hotel

• 455 S Broadway, Tarrytown, NY 10591-6002
• (914) 631-5700
• Rooms between $130-$170 on average
• Find Out More Here

Sleepy Hollow is such a great little town, and it’s even more charming once the trees start dropping their leaves. Get out and enjoy the autumn sunshine in this Hudson Valley gem! Have you been to Sleepy Hollow? Did you love it?

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