New York

24 Hours in Sleepy Hollow

by Holly Riddle  |  Published March 3, 2020

Yes, Sleepy Hollow isn’t just a fictional town in Washington Irving’s legend by the same name. It’s a real place, with history, culture and a great love for a good spook.

Cemeteries and historic buildings are par for the course in Sleepy Hollow (Photo: Holly Riddle)

Sleepy Hollow is a small village in New York, about an hour’s drive outside New York City. While there is more to this destination than its association to Washington Irving’s short story “The Legend of Sleepy Hollow,” the village clings to its spooky connection to the Headless Horseman with fervor, luring many a curious traveler, particularly around Halloween.

In reality, Sleepy Hollow’s history predates that of the United States. It was an agricultural center in the Dutch New Netherlands, centered around the Philipse family and their expansive land ownership. The Loyalist Philipse family was forced to turn their land over to the newly established U.S. government following the Revolutionary War, at which point a small hamlet was popping up around a nearby mill, which visitors can still see today, along with the Philipse family’s manor.

The Philipsburg Manor predates current-day Sleepy Hollow  (Photo: Daniel Mennerich via Flickr / CC BY-NC-ND 2.0)

Eventually, the little hamlet incorporated into a village named North Tarrytown. It wasn’t until 1996 that the name of Sleepy Hollow was adopted to distinguish North Tarrytown from its neighbor Tarrytown, to the south. The name was a nod to the area’s history and connection to Washington Irving’s story, set in what was North Tarrytown at the time of the story’s writing.

Visiting Sleepy Hollow is convenient, thanks to its proximity to New York City and many major highways running nearby. Tip: Rent a car to fully explore the village and surrounding areas.

Things to Do

The Old Dutch Church and its graveyard attract travelers in droves (Photo: Holly Riddle)

Easily the most famous site in Sleepy Hollow, the Old Dutch Church and Graveyard (430 North Broadway) was where Ichabod Crane hoped to find refuge from the Headless Horseman in “The Legend of Sleepy Hollow.” Today, the real-life church, dating back to the 17th century, offers free guided tours of the graveyard in the summer, but you can find self-guided tour books in tourist shops around town. The historic church is nicely preserved, and the graveyard contains headstones for locals who lived through the American Revolution.

See famous names among the headstones at Sleepy Hollow Cemetery (Photo: Holly Riddle)

Adjacent to the Old Dutch Church and Graveyard is Sleepy Hollow Cemetery (540 North Broadway). For anyone interested in dark tourism, and anyone who likes a little history, this spot is a must-visit. The types of gravestones range wildly, from rural Victorian headstones to huge mausoleums holding the richest deceased. Famous people buried here include not only the town’s beloved Washington Irving, but also Andrew Carnegie, Elizabeth Arden, William Rockefeller and Walter Chrysler.

Walk down the road just a ways from Sleepy Hollow Cemetery and snap a photo of the Headless Horseman Bridge (Photo: Daniel Mennerich via Flickr / CC BY-NC-ND 2.0)

Speaking of the Rockefellers, the John D. Rockefeller Estate (200 Lake Road, Pocantico Hills), also known as Kykuit, is open to the public, or at least the main house is, along with the art gallery and garden. The 40-room historic home housed four generations of Rockefellers and is now a National Historic Landmark. The estate takes its name from the Dutch word meaning “lookout,” as it sits at the highest elevation point within the Pocantico Hills, affording views of the Hudson River and even the New York City skyline, 25 miles away. You can visit the estate from mid-May until early November.

The Rockefeller Estate looks out over much of the surrounding landscape (Photo: ERiKA via Flickr / CC BY-NC 2.0)

For a glimpse of life back in the 1600s, visit the Philipsburg Manor Upper Mills (381 North Broadway), around which the original hamlet bloomed. The historic Dutch manor makes an appearance in “The Legend of Sleepy Hollow” as a place where Ichabod Crane was known to take a leisurely, outdoor stroll with the local ladies.

Get your fill of Washington Irving and the lore surrounding the author at his restored estate, Sunnyside (3 West Sunnyside Lane, Irvington), where you can see artifacts from Irving’s life, such as his books and writing desk. Living history guides walk guests around the grounds and house, touching on Irving’s views on life and how they relate to the scenery. On select dates, the historic property hosts spooky events, such as educational opportunities to learn more about what might’ve frightened Irving when he was alive, including Victorian trends like seances and vampire tales.


There are no accommodations strictly within Sleepy Hollow, but there are several located a quick drive from the village’s main attractions.

Castle Hotel and Spa (400 Benedict Avenue, Tarrytown) is one of the more luxurious options. The castle was built in 1897 and is now a historic landmark. Just over 30 guestrooms and suites offer unique amenities, such as wood-burning fireplaces, access to walking trails, a bocce court and more. The on-site dining and spa are not to be missed, and, of course, the hotel provides modern amenities like complimentary WiFi.

Similarly, Tarrytown House (49 East Sunnyside Lane) is an estate hotel set in a 19th-century mansion that overlooks the Hudson River. Guestrooms offer views of the New York City skyline and updated, contemporary furnishings.

For those looking to save their pennies for spending in Sleepy Hollow, several affordable options are also available, such as the Bricktown Inn (112 Hudson Avenue, Haverstraw), a colonial establishment set in the former brick-making capital of the Northeast. Casa Hudson Penzione (34 First Street, Haverstraw), another historic brick home, also boasts views of the Hudson.

Like a Local: Restaurants, Bars & Cafés

The prix fixe menu at Blue Hill at Stone Barns is always impressive (Photo: Lou Stejskal via Flickr / CC BY 2.0)

J.P. Doyles Restaurant & Public House (48 Beekman Avenue) serves comfort food in an Irish pub-style setting. The restaurant is an easy walk from some of Sleepy Hollow’s top attractions and also offers a beer garden that’s open during warm weather. The menu includes typical pub fair, alongside salads, pastas and burgers. Try the bacon, cheddar and chili-topped Horseman Burger for a little bit of local flair.

For seasonal, farm-to-table finds, look no further than Hudson Farmer & The Fish (11 River Street). Owned by a farm located north of Sleepy Hollow, the outpost prides its fresh ingredients, with fare ranging from a full raw bar to pizza, and more. Outdoor dining overlooks the Hudson, while the open kitchen allows guests to get up close and personal with the chef’s counter.

Blue Hill at Stone Barns (630 Bedford Road) was created by Dan Barber, who owns a successful restaurant in Manhattan’s Greenwich Village. The upscale eatery is set inside the Stone Barns Center for Food and Agriculture. Check the dress code online before you make reservations. Once there, dive into a memorable prix fixe menu, touting only the freshest ingredients, culled from a range of sources–from the greenhouse, field, and pasture to the forest, farm and cellar.

If you fancy Greek dining, Santorini Greek Restaurant (175 Valley Street) has you covered with its family Mediterranean and Grecian menus. The restaurant, which has been reviewed by The New York Times, offers all the classic Greek favorites, from spanakopita to saganaki, moussaka to kataifi.

Bridge View Tavern (226 Beekman Avenue) offers (obviously) bridge and Hudson views from a cozy, local atmosphere. The tavern’s specialty drinks during the fall and winter include a pumpkin apple spice sangria and the Jack O’ Lantern, a mix of whiskey, maple syrup, orange and cherries. Lunch and dinner menus feature burgers, steak, sandwiches, soups and salad.


The shopping scene in Sleepy Hollow is always good for a unique find, as the storefronts primarily consist of vintage and thrift shops.

Try Bella’s Boutique (35 North Broadway) for a huge range of jewelry, apparel and home decor. You’re sure to find something that fits your style, no matter what that style might be. The boutique is also noted as being the place to find memorabilia and art with a “Legend of Sleepy Hollow” connection.

Pretty Funny Vintage (80 South Broadway) is an eclectic vintage shop situated within an equally vintage home, decorated in an 1890s Victorian style. Search through furniture, textiles, jewelry, clothing and curious goods of all types.

For the crafter, Flying Fingers Yarn Shop (15 Main Street) provides everything you need to complete your next project. Shoppers can easily spend over an hour in the storefront, perusing the wide array of materials.