From the ghoulish events and lantern lights of Halloween to tours of historic estates and lazy summer day picnics in the park to experiencing The Legend of Sleepy Hollow by Washington Irving, Sleepy Hollow is full of things to do any time 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’ve been to Sleepy Hollow many times and we never fail to find something new and interesting to do. We recommend going more than once: first for Halloween, and then again as part of a visit to the Hudson Valley to enjoy the charm and historic sites at a less crowded and more leisurely pace. Or do as we have done, go often and in every season.
Since Washington Irving and The Legend of Sleepy Hollow are so important to the town — once called North Tarrytown, the town changed its name to Sleepy Hollow in 1996 — we’ll start with the sites related to the story.
1. Sleepy Hollow Cemetery
Let’s begin with the Sleepy Hollow Cemetery. The cemetery is a prominent feature in The Legend of Sleepy Hollow and it’s a good place to begin your orientation to the town. Irving is buried in the cemetery. Don’t expect to get too close to Irving’s grave, though — it is protected by a fence. If you visit during the month of October, you will likely find throngs of young people in costumes in the cemetery. In addition to Irving, the cemetery is the final resting place for a number of historical figures, including Andrew Carnegie, Samuel Gompers, Elizabeth Arden, and Brooke and Vincent Astor. You’ll also find memorials for Civil War soldiers.
Pro Tip: The cemetery is very large, approximately 90 acres. It’s best to pick up a map so that you’re not wandering aimlessly. There are also guided tours, especially in October.
2. Dutch Reform Church
Founded around 1685, the Dutch Reform Church is also featured in The Legend of Sleepy Hollow. Ichabod Crane was in a mad dash to get to the church before the headless horseman got to him. Still, with an active congregation, the church has been in continuous operation since the late 1600s. The cemetery is the burial ground for the church.
Pro Tip: The church is open for very limited hours on the weekends. If you are there when the church is closed, it’s still beautiful to see it from the outside. You’ll see it right before you walk into the cemetery.
3. Headless Horseman Bridge
Another must-see location in Sleepy Hollow is the Headless Horseman Bridge. If you’re walking through the cemetery, take a detour to the bridge. The bridge over the Pocantico River where Ichabod Crane falls off his horse no longer exists. Despite the lack of historical accuracy, this bridge is still a picturesque spot for a picture or selfie.
Pro Tip: If you’re short on time or not a diehard Irving fan, we recommend skipping this stop.
4. Headless Horseman Sculpture
Spend a few minutes taking a photo of the Headless Horseman Sculpture. It’s a depiction 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 Manor.
5. Philipsburg Manor
Stop by the Philipsburg Manor which also makes an appearance in Irving’s story. Frederick Philipse came to the Hudson Valley in 1653 as a carpenter. His family ended up owning more than 50,000 acres in the Hudson Valley. In 1750, the manor was a working farm that relied on the labor of 23 slaves, making the Philipses one of the largest slaveholding families in the northern colonies. The museum now depicts the history of the slaves during that period.
6. Washington Irving’s Sunnyside Estate
Washington Irving’s Sunnyside Estate is an important stop in Sleepy Hollow. He bought the two-room Dutch house in 1835 and extensively remodeled it. Make sure to wander the grounds to admire the landscaping. You’ll see guides in period costumes and experience what Irving’s life would’ve been like. The estate is wheelchair accessible.
Pro Tip: While not officially 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 was formerly the estate of the Rockefellers. If you like architecture, landscapes, art, gardens, or just seeing how the wealthiest people lived, Kykuit is a must-see. You could spend almost a whole day wandering the grounds of Kykuit. The gardens and sculptures are impressive. Make sure to see the table that had water floating in the middle for passing dinner dishes.
Pro Tips: We recommend good walking shoes for this excursion. You cannot go into the grounds of Kykuit without booking a guided tour and it is best to book in advance. If you have a chance, we recommend the tour that includes the art galleries. It is an amazing collection. There are other tours that bring you into the main house and the gardens.
8. Rockefeller Park Preserve
The Rockefeller Park preserve is a wonderful spot for a picnic, a hike, or even a ride on a horse. There are wetlands and a lake. If you are a bird lover, it’s a great place for birdwatching. Most of the 55 miles of trails were laid out by John D. Rockefeller, Sr., and other members of the family.
Pro Tip: Most of the trails are easy but you still want to have a pair of walking shoes.
9. Armour-Stiner (Octagon) House
Make sure to stop by the octagon house to at least take a picture from the outside. It’s a private residence now, though there are some tours that you can book in advance. The octagon house is unique in that … It’s an octagon. Built in the 1860s, it’s like an ancient classical temple. It’s worth seeing from the outside and inside.
10. The Union Church Of Pocantico Hills
When we are in the Hudson Valley, we always try to stop by the Union Church of Pocantico Hills. Technically, it’s in Tarrytown, but it is a mere stone’s throw away from Sleepy Hollow. It’s such a hidden gem that we must include it. Henri Matisse created the rose window — it was his last work before he died. Marc Chagall created the remaining stained-glass windows. The church was commissioned by the Rockefeller family, and many have worshipped there over the years.
Pro Tip: They don’t allow photographs to be taken inside, so you’ll just need to enjoy the experience.
Sleepy Hollow Restaurants
There are a lot of places to eat in Sleepy Hollow and the surrounding towns, including neighboring Tarrytown. For farm-to-table and local food, we recommend these four restaurants.
Hudson Farm & The Fish
If you are looking for a restaurant with great food and wonderful views of the Hudson River in Sleepy Hollow, go no further than Hudson Farm & the Fish. It features farm-to-table (with Purdy’s Farm and the restaurant being owned by the same people), and they also have a full raw bar, excellent pizza, and many craft beers on tap.
J.P Doyle’s Restaurant & Public House
J.P Doyle’s is a local hangout. It’s an Irish pub with comfort food galore. During warm weather, there’s an outdoor beer garden. It’s also a sports bar, so if you must watch a game while in Sleepy Hollow, this is the place to go. J.P.’s is walking distance from Sleepy Hollow Cemetery and Philipsburg Manor.
Blue Hill At Stone Barns
For an upscale farm-to-table experience, try Blue Hill at Stone Barns (in 2019, Michelin gave it two stars). Don’t expect to see a menu. Instead, you’ll experience a multi-course feast chosen by the chef based on what produce is currently in season. We recommend taking a tour of the farm while you’re there. You’ll need to make a reservation well in advance to get a table. Also on site, the Blue Hill Café and Grain Bar is less expensive and much easier to get into.
Technically in Tarrytown, Goosefeather is a short drive from Sleepy Hollow. Chef Dale Talde created Goosefeather as a place for upscale Cantonese food with a modern twist. He uses Hudson Valley produce to create a unique dining experience. It is a great setting for a romantic dinner. Goosefeather is located within Tarrytown House Estate, a very nice place to stay if you are in the area.
Full of history, drama and intrigue, literary references, parks, and dining experiences, there’s something for everyone and every season in Sleepy Hollow.
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