10 best things to do in Sleepy Hollow

From ghoulish events and Halloween lanterns to tours of historic estates and lazy summer picnics in the park to experience The legend of Sleepy Hollow by Washington Irving, Sleepy Hollow is full of things to do anytime of the year. If you love history, food, architecture, and nature, you’ll want to put Sleepy Hollow on your list of places to go.

We have been to Sleepy Hollow several times and never fail to find something new and interesting to do. We recommend going there more than once: first for Halloween, then again as part of a visit to the Hudson Valley to enjoy the charm and historic sites at a less crowded pace and quieter. Or do as we did, go there often and every season.

From Washington Irving and The legend of Sleepy Hollow is so important to the city – formerly called North Tarrytown, the city changed its name to Sleepy Hollow in 1996 – we’ll start with the sites related to history.

Photo credit: Regina Ang / Travel For Life Now

1. Pay homage to Sleepy Hollow Cemetery

Let’s start with Sleepy Hollow Cemetery. The cemetery is an important element in The legend of Sleepy Hollow and it’s a good place to start your orientation towards the city. Irving is buried in the cemetery. Don’t expect to get too close to Irving’s Grave, it’s protected by a fence. If you visit during the month of October, you will likely find crowds of young people in costumes in the cemetery. In addition to Irving, the cemetery is the final resting place of a number of historical figures, including Andrew Carnegie, Samuel Gompers, Elizabeth Arden and Brooke and Vincent Astor. You will also find memorials for the soldiers of the Civil War.

Pro tip: The cemetery is very large, around 90 acres. It is better to take a map so as not to wander aimlessly. There are also guided tours, especially in October.

The Dutch Reformed Church, Sleepy Hollow, New York.
Photo credit: Sue Davies / Travel For Life Now

2. See the Dutch Reformed Church

Founded around 1685, the Dutch Reformed Church is also present in The legend of Sleepy Hollow. Ichabod Crane was in a mad rush to get to the church before the Headless Horseman reached him. Yet with an active congregation, the church has been in continuous operation since the late 1600s. The cemetery is the burial place of the church.

Pro tip: The church is open for very limited hours on weekends. If you are there when the church is closed, it is still beautiful to see it from the outside. You will see it just before entering the cemetery.

The Headless Horseman's Bridge in Sleepy Hollow, New York.
Photo credit: Regina Ang / Travel For Life Now

3. Take a photo at the Headless Horseman’s Bridge

Another must-see spot in Sleepy Hollow is the Headless Horseman’s Bridge. If you cross the cemetery, take a detour over the bridge. The bridge over the Pocantico river where Ichabod Crane falls from his horse no longer exists. Despite the lack of historical precision, this bridge is still a scenic spot for a photo or selfie.

Pro tip: If you’re short on time or aren’t a die-hard Irving fan, we recommend skipping this stop.

Headless Horseman sculpture located in near Philipsburg Manor, Sleepy Hollow, New York.
Photo credit: Sue Davies / Travel For Life Now

4. Admire the sculpture of the Headless Horseman

Take a few minutes to snap a photo of the Headless Horseman sculpture. It’s a description of the moment in Irving’s book when the Headless Horseman throws the pumpkin at Ichabod Crane. It’s on Route 9 right across from the Philipsburg Mansion.

Philipsburg Manor property located in Sleepy Hollow, New York.
Photo credit: Sue Davies / Travel For Life Now

5. Experience history at Philipsburg mansion

Stop at the Philipsburg Mansion which also makes an appearance in Irving History. Frederick Philipse arrived in the Hudson Valley in 1653 as a carpenter. His family ended up owning over 50,000 acres in the Hudson Valley. By 1750 the mansion was a working farm that depended on the labor of 23 slaves, making the Philips one of the largest slave families in the northern colonies. The museum now depicts the history of slaves during this period.

Washington Irving's Sunnyside Estate located near Tarrytown, New York.
Photo credit: Kenneth Sponsler / Shutterstock

6. Visit the Sunnyside Estate

Washington Irving’s Sunnyside Estate is a landmark in Sleepy Hollow. He bought the two-room Dutch house in 1835 and extensively renovated it. Be sure to walk around the grounds to admire the landscaping. You’ll see guides in period costume and learn about what Irving’s life would have been like. The estate is wheelchair accessible.

Pro tip: Although not officially located in Sleepy Hollow, Lyndhurst Castle (mansion) is just 2 miles away. One of the best examples of Gothic Revival architecture, the mansion has 19 rooms and 67 acres of gardens. There are many more historic mansions to see in the Hudson Valley.

Kykuit, the former estate of the Rockefeller family.
Photo Credit: Photo Spirit / Shutterstock

7. Spend time in Kykuit

Kykuit was once the home of the Rockefellers. If you love architecture, scenery, art, gardens, or just seeing how the wealthiest people used to live, Kykuit is a must see. You could spend almost a whole day wandering the Kykuit Gardens. The gardens and the sculptures are impressive. Make sure you see the table which had water floating in the middle to pass the dinner dishes.

Pro tips: We recommend good walking shoes for this excursion. You cannot enter Kykuit Park without booking a guided tour and it is best to book in advance. If you have the chance, we recommend the tour which includes the art galleries. It’s an incredible collection. There are other tours that take you into the main house and gardens.

Pathway bridge located in the Rockefeller Park Reservation, Sleepy Hollow, New York.
Photo credit: Kyle Tunis / Shutterstock

8. Take a walk in the Rockefeller Park reserve

The Rockefeller Park Preserve is a wonderful place for a picnic, a hike, or even a horseback ride. There are wetlands and a lake. If you are a bird lover this is a great place for bird watching. Most of the 55 miles of trails were made by John D. Rockefeller, Sr., and other family members.

Pro tip: Most of the trails are easy, but you still want to have a pair of walking shoes.

9. The Armor-Stiner House (Octagon)

Make sure to stop by the octagonal house to at least take a photo of the exterior. It is now a private residence, although there are tours that you can book in advance. The octagonal house is unique in this sense… It is an octagon. Built in the 1860s, it is like an old classical temple. It is worth seeing from the outside and the inside.

Pocantico Hills Union Church, Tarrytown, New York.
Photo credit: Linda Harms / Shutterstock

10. Be enchanted by the Union Church of Pocantico Hills

When we are in the Hudson Valley we always try to stop at the church. Technically, it’s in Tarrytown, but it’s a short walk from Sleepy Hollow. It’s such a hidden gem that we have to include it. Henri Matisse created the rose window – it was his last work before his death. Marc Chagall produced the remaining stained glass windows. The church was commissioned by the Rockefeller family, and many have worshiped there over the years.

Pro tip: They do not allow taking pictures indoors, so you will only have to enjoy the experience.

Exterior view of Goosefeathers Restaurant, Sleepy Hollow, New York.
Goose feathers (Photo credit: Sue Davies / Travel For Life Now)

Places to eat

There are plenty of places to eat in Sleepy Hollow and the surrounding towns, including the nearby town of Tarrytown. For farm-to-table and local cuisine, we recommend these four restaurants.

Hudson Farm and the Fish

If you’re looking for a restaurant with great food and great views of the Hudson River in Sleepy Hollow, look no further than Hudson Farm & the Fish. It offers farm-to-table (with Purdy’s Farm and the restaurant owned by the same people), and they also have a full bar, great pizzas, and plenty of craft beers on tap.

JP Doyle restaurant and pub

JP Doyle’s is a local hangout. It’s an Irish pub with comfort food galore. In warm weather, a beer garden is available. It’s also a sports bar, so if you have to watch a game at Sleepy Hollow this is the place to go. JP’s is a short walk from Sleepy Hollow Cemetery and Philipsburg Mansion.

Blue Hill at Stone Barns

For an upscale farm-to-table experience, try Blue Hill at Stone Barns (in 2019, Michelin awarded it two stars). Don’t expect to see a menu. Instead, you’ll experience a chef-chosen multi-course feast based on seasonal produce. We recommend that you take a tour of the farm while you are there. You will need to book well in advance to get a table. Also on site, the Blue Hill Café and Grain Bar is cheaper and much easier to access.

Goose feathers

Technically in Tarrytown, Goosefeathers is a short drive from Sleepy Hollow. Chef Dale Talde created Goosefeathers as a place for upscale Cantonese cuisine with a modern twist. He uses products from the Hudson Valley to create a unique dining experience. It is an ideal setting for a romantic dinner. Goosefeathers is located in Tarrytown House Estate, a lovely place to stay if you are in the area.

Full of history, drama and intrigue, literary references, parks and culinary experiences, there is something for everyone and every season at Sleepy Hollow.

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