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?
The Basics:
Where Is Sleepy Hollow?
Sleepy Hollow is a ‘sleepy’ small town in the Hudson Valley, steeped in history and the Legend of the Headless Horseman and Ichabod Crane. It’s known as the setting of Washington Irving’s The Legend of Sleepy Hollow. Irving is even buried in Sleepy Hollow Cemetery.
How Do I Get To Sleepy Hollow?
Air –
The closest airport is Westchester County Airport, it’s incredibly small, and you will pay a premium for convenience. The largest airport near Sleepy Hollow is JFK, it will take about an hour to drive from JFK to Sleepy Hollow. You will need a rental car if you are flying in.
Drive –
Sleepy Hollow is an easy road trip for most of New England, New York, Pennsylvania, and New Jersey.
When Should I Go?
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
William J. Wilgus (1819–53), artist Chromolithograph, c. 1856. Wikipedia.
“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
Where To Eat In Sleepy Hollow
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.
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!
J.P. Doyle’s Restaurant
- 48 Beekman Ave, Sleepy Hollow, NY 10591
- (914) 631-3015
- Daily 12-10 pm
- Good food, friendly service, gluten-free friendly, pub-style place
Horsefeathers (in Tarrytown)
- 94 N Broadway, Tarrytown, NY 10591
- (914) 631-6606
- Mon: Closed, Tues: 3-9 pm, Wed-Thurs, Sun: 12-9 pm, Fri-Sat: 12-9:30 pm
- Great atmosphere, cozy, great music, friendly service
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
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
- Dates have not yet been announced for 2023
- 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.
Irving’s Legend
- Sunnyside, 3 W Sunnyside Lane, Irvington, NY 10533
- Dates For 2023 Have Not Been Announced Yet
- Advanced Reservations Required – Buy Tickets HERE
Performed under the stars by storyteller Jonathan Kruk in a dramatic performance of the classic tale, The Legend Of Sleepy Hollow. Live music and an appearance from the Headless Horseman himself make this spooky event an experience for all ages!
Sleepy Hollow Haunted Hayride
- Sleepy Hollow Village Hall, 28 Beekman Avenue, Sleepy Hollow, NY 10591
- Dates For 2023 Have Not Been Announced Yet
- They will go on sale HERE
On this haunted hayride, you take the exact same path that Ichabod Crane did, past Old Dutch Church, then through the iron gates to the dark woods of the hollow. You’ll probably hear hoofbeats, and if you do, make sure to watch out for your head! There is also a block party before and after the hayride.
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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