There are plenty of things to do in Sleepy Hollow throughout the year, from the spooky activities and lantern-lit nights of Halloween to the leisurely lunches in the park on lazy summer days and the tours of historic estates. You should add Sleepy Hollow to your list of travel destinations if you enjoy nature, history, cuisine, architecture, and all of these things.
Despite our frequent visits to Sleepy Hollow New York, we are always able to discover something fresh and exciting to do. To savour the beauty and historic monuments at a less hurried and more leisurely pace, we advise travelling twice: once for Halloween and once as part of a trip to the Hudson Valley. Alternately, go frequently and in all four seasons as we have.
We’ll start with the locations associated with the tale since Washington Irving and The Legend of Sleepy Hollow are so significant to the town — formerly known as North Tarrytown before changing its name to Sleepy Hollow in 1996.
1. Sleepy Hollow Cemetery
Starting with Sleepy Hollow Cemetery, please. You should start becoming acquainted with the town at the cemetery, which plays a significant role in The Legend of Sleepy Hollow. The cemetery is where Irving is interred. However, don’t anticipate being able to approach Irving’s grave very closely; a fence surrounds it. If you go in October, the cemetery will probably be packed with kids wearing costumes. Along with Irving, other notable luminaries who are buried there include Andrew Carnegie, Samuel Gompers, Elizabeth Arden, and Brooke and Vincent Astor. Additional monuments are honouring Civil War veterans.
About 90 acres make up the cemetery’s size. Pick up a map as soon as possible to avoid aimlessly wandering. Additionally, there are guided tours, particularly in October.
2. Dutch Reform Church
The Dutch Reform Church, which dates back to 1685, is also mentioned in The Legend of Sleepy Hollow. Before the headless horseman caught up with him, Ichabod Crane made a hasty retreat to the chapel. The church has been in continuous operation since the late 1600s and still has a thriving congregation. The church’s graves are located in the cemetery.
On the weekends, the church is only open for a very short time. Even though the church is shut down, the exterior is still lovely to behold. Right before you enter the cemetery, you’ll see it.
3. Headless Horseman Bridge
The Headless Horseman Bridge is another spot in Sleepy Hollow that should not be missed. Take a side trip to the bridge if you’re passing through the cemetery. Ichabod Crane falls from his horse over a bridge over the Pocantico River, but that bridge is no longer there. Although not historically accurate, this bridge is nevertheless a beautiful location for a photo or selfie.
We advise avoiding this stop if you’re pressed for time or aren’t a die-hard Irving supporter.
4. Headless Horseman Sculpture
Take a few minutes to capture the Headless Horseman sculpture on camera. It is a representation of the scene in Irving’s book where Ichabod Crane is struck by the pumpkin thrown by the headless horseman. Route 9, it is just across from Philipsburg Manor.
5. Philipsburg Manor
Visit the Philipsburg Manor, which is a location in Irving’s story as well. As a carpenter, Frederick Philipse arrived in the Hudson Valley in 1653. In the end, his family possessed more than 50,000 acres of land in the Hudson Valley. The Philips were one of the largest slaveholding families in the northern colonies in 1750 when the manor was a working farm that relied on the labour of 23 slaves. The history of the slaves during that time is now represented in the museum.
6. Sunnyside Estate of Washington Irving
One of the most significant stops in Sleepy Hollow is Washington Irving’s Sunnyside Estate. In 1835, he purchased the two-room Dutch house and made significant renovations. Wander the grounds and take in the landscaping. You’ll observe tour guides dressed historically and get a sense of what Irving’s life was like. Wheelchair users can access the estate.
Lyndhurst Castle (Mansion), though not formally in Sleepy Hollow, is only two miles away. The mansion includes 19 rooms and 67 acres of gardens, and it is considered one of the outstanding specimens of Gothic Revival architecture. The Hudson Valley is home to many more historic homes.
The Rockefellers once owned the estate of Kykuit. Kykuit is a must-see if you enjoy landscapes, art, gardening, architecture, or simply learning about how the richest people formerly lived. The grounds of Kykuit might easily keep you busy for an entire day. Impressive sculptures and gardens can be found here. Make sure to look at the dinner-passing table with the water in the centre.
For this excursion, dependable walking shoes are advised. Without making a guided tour reservation—which is advised—you cannot enter the Kykuit grounds. We advise taking the tour that includes the art galleries if you get the chance. It’s an incredible collection. Other excursions allow you to visit the main home and the gardens.
8. Rockefeller Park Preserve
The Rockefeller Park preserve is a great place for a hike, a picnic, or perhaps a horseback ride. A lake and wetlands are present. It’s a fantastic location for birdwatching if you love birds. John D. Rockefeller, Sr. and other family members designed the majority of the 55 miles of trails.
Even though the majority of the routes are simple, you should still wear walking shoes.
9. Armour-Stiner House (Octagon)
Be sure to visit the octagon house at least once so you may snap a photo of the exterior. Although you can reserve some tours in advance, it is currently a private residence. The octagon house is distinctive because… It is an octagon. It resembles an old classical temple and was constructed in the 1860s. Both the inside and the outdoors are worth visiting.
10. Pocantico Hills’ Union Church
We always make an effort to visit the Union Church of Pocantico Hills when we are in the Hudson Valley. Though it is technically in Tarrytown, Sleepy Hollow is just a short distance away. We must include it because it is such a rare find. The rose window was Henri Matisse’s final piece of art before his passing. The remaining stained-glass windows were made by Marc Chagall. Many people have worshipped there over the years since the Rockefeller family funded the construction of the chapel.
You will just have to enjoy the experience because taking photos inside is not permitted.
Sleepy Hollow Restaurants
There are many dining options in Sleepy Hollow and the other communities, including Tarrytown. We suggest these four eateries for local and farm-to-table cuisine.
Hudson Farm & The Fish
Go no further than Hudson Farm & the Fish if you’re looking for a restaurant in Sleepy Hollow with delicious meals and stunning Hudson River views. It offers farm-to-table cuisine and has a full raw bar, outstanding pizza, and a wide selection of craft beers on tap. Purdy’s Farm and the restaurant are owned by the same individuals.
J.P Doyle’s Restaurant & Public House
Locals frequent J.P. Doyle’s. It is an Irish bar with an abundance of comfort food. There is an outside beer garden throughout the summer. It also serves as a sports bar, so if you have to watch a game while in Sleepy Hollow, head here. Philipsburg Manor and Sleepy Hollow Cemetery are both close to J.P.’s.
Blue Hill At Stone Barns
Try Blue Hill at Stone Barns for an elegant farm-to-table dining experience (in 2019, Michelin gave it two stars). Expect not to see a menu. Instead, you’ll partake in a multi-course feast that the chef has selected based on the seasonality of the ingredients. While you’re there, we advise taking a tour of the farm. To secure a table, you must make a reservation far in advance. The Blue Hill Café and Grain Bar is another establishment there, and it’s less expensive and much simpler to enter.
Goosefeather is technically in Tarrytown, although it’s only a short drive to Sleepy Hollow. Goosefeather was established by chef Dale Talde as a location for upmarket Cantonese cuisine with a contemporary touch. He makes a special eating experience by utilising produce from the Hudson Valley. The environment is ideal for a special dinner for two. Tarrytown House Estate, a very nice place to stay if you’re in the area, is where Goosefeather is situated.
There is something for everyone and every season in Sleepy Hollow, which is full of history, drama and intrigue, literary allusions, parks, and dining opportunities.