The Hudson River town of Sleepy Hollow, NY, has a long history of attracting tourists. It offers breathtaking views, a historic city brimming with things to do, and a wonderful family atmosphere as it perches on the banks of the Hudson River. The Rockefeller family, who are considered royalty in New York State, made the hamlet one of their favorite homes. The community’s history is anchored in Native American tribes and, later, European farmers.
Visitors and residents alike have plenty of opportunities to enjoy nature in the hills that rise from the banks of the Hudson River because the surrounding area is protected territory. Whether you like history, art, culture, or outdoor activities, Sleepy Hollow, NY, is a famous tiny town in New York State that you shouldn’t miss.
Read on to discover the best things to do in Sleepy Hollow, NY.
#1. Explore Kykuit Estate
Since the Rockefeller family made millions in the petroleum sector in the 19th century, they are considered to be close to New York royalty. In Sleepy Hollow, where Kykuit, the Rockefeller Estate, a colonial-style mansion built in 1913 by John D. Rockefeller, is located, they have left their imprint.
It has a six-story height, an ivy-draped stone façade with archways, and immaculately kept grounds. Rockefeller’s magnificent private collection of modern artwork, which includes works by Picasso, Calder, Henry Moore, and Andy Warhol, is kept in the mansion’s basement. Even though the family still owns the mansion, it is now accessible to the public.
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#2. Sleepy Hollow Cemetery
There are a lot more long-term residents in Sleepy Hollow Cemetery. The organization’s website states that the cemetery has a little under 50,000 burials. There are excursions available that tell the legend of Sleepy Hollow, NY, and the tales of Washington Irving, his Headless Horseman. Along with breathtaking views of the Hudson River, visitors can visit the graves of John D. Rockefeller, Walter Chrysler, and Andrew Carnegie, among others. It should be mentioned that only daytime excursions or open hours are permitted to visit Irving’s grave.
#3. Spend Some Time at Philipsburg Manor
A historic home in New York State with the name Philipsburg Manor was formerly held by European farmers. 23 slaves of African heritage lived there in the midst of a bustling grist mill. To raise awareness of American slavery and agricultural life in the 18th century, it now functions as a living museum. Tourists can tour the manor’s exterior and inside to see replicas of historical items and artifacts from the era. The on-site staff members dress up and narrate tales of the manor’s former owners, the Philipse family.
#4. Headless Horseman Bridge
The Headless Horseman Bridge is another spot in Sleepy Hollow, NY, that you should not miss. 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.
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#5. Walk Through Irving’s Home
The literary landscape appears to be a magical world to those who observe it from a distance, but like all other landscapes, the allure wears off as you get closer and you can see the thorns and briars. You must visit Irving’s home, Sunnyside, if you can’t get enough of his history and other Sleepy Hollow, NY, figures. Along the Hudson River, Sunnyside is a portion of the Philipsburg Estate (more on that below). Given its previous occupants, Irving’s house appears to have come right out of a book. Even Irving’s office is visible when in Sunnyside.
#6. Explore the Old Dutch Church
Many people are familiar with the famous Washington Irving story “The Legend of Sleepy Hollow,” but few are aware that it is based on a real location. The Sleepy Hollow of Irving’s Day was a really real place, and it served as the basis for his eerie Headless Horseman story. The Old Dutch Church, New York’s oldest standing church, served as the inspiration’s actual location.
The Sleepy Hollow Old Dutch Church is the building that once housed the Sleepy Hollow Cemetery. It was started in 1685 and is still going strong today. The church gained national historic landmark status in the 1960s. Every fall, hundreds of people travel to the church and its grounds to experience the eerie location firsthand and to participate in the seasonal activities that highlight the town’s well-known mythology.
#7. The Union Church of Pocantico Hills
Though it is technically in Tarrytown, Sleepy Hollow, NY, is just a short distance away. We have to 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 worshiped there throughout the years since the Rockefeller family funded the construction of the chapel. You’ll just have to have fun with the experience, as they allow photos inside.
#8. See the Bronze Lady
A huge bronze statue of a woman is located inside Sleepy Hollow Cemetery, next to the burial of Civil War general Samuel Thomas, and is rumored to be haunted. The Bronze Lady is said to have a curse on her that affects anyone who sits on her lap, leaps down, and spins three times before looking at her. Her legends go further than that, though.
According to a different belief, you can see a ghost if you sit on her lap and look into Thomas’ mausoleum door across the street. Others assert that you will suffer bad luck if you offend the statue or curse yourself if you touch her face. Regardless of the mythology you choose to believe, it makes the ominous statue appear a little bit more terrifying.
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#9. Explore Rockefeller State Park Preserve
The old Pocantico Hills and Rockwood Hall county estates of John D. Rockefeller are now popular as the Rockefeller State Park Preserve. In order to protect wildlife and natural beauty for the future, it was given to the state of New York. Visitors can now travel 45 miles of picturesque carriage routes that pass Swan Lake, the Pocantico River, stone bridges, and breathtaking vistas.
Still standing in a stunning area of the preserve with views of the Hudson River and Palisade Cliffs is the old Rockwood Hall mansion. From 1886 to 1922, William Rockefeller resided in the 202-room house known as Rockwood Hall.
#10. Go Shopping at the Farmer’s Market
In this Hudson River neighborhood, the Tarrytown-Sleepy Hollow Farmers Market (TaSH) is an essential institution. Every Saturday, the market is open in Patriots Park, which is located on the boundary of Tarrytown and Sleepy Hollow. The two towns of Tarrytown and Sleepy Hollow are right next to one another and mix together. Locals and tourists have been waiting in line every Saturday since 2015 to purchase fresh vegetables, loaves of bread, baked goods, meats, cheeses, artisanal prepared dishes, and other items. Over 30 vendors are present throughout the park in full form.
Live entertainment is available at all times, ranging from chef displays and kid’s activities to painting courses, alongside the kaleidoscope of vibrant products. Every year during the holidays, TaSH holds its Tree Lighting Festival and Christmas pop-up marketplace, which is always a joyous and merry experience for locals and guests.
#11. Spot Chagall and Matisse
This little Hudson River village is one of the best places to enjoy Marc Chagall’s and Henri Matisse’s artwork. It’s no surprise that this Westchester County community has lots of gifts with top-notch art when its residents include the Rockefellers.
The Union Church of Pocantico Hills, which is close to Kykuit, is home to some magnificent though little-known stained-glass creations by Matisse and Chagall. Start with Matisse’s rose window, which also happens to be his final piece before passing away in 1954. Chagall created nine windows for the church, the most well-known of which is the Good Samaritan window.
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#12. Unwind at Castle Hotel and Spa
There are many lovely hotels and spas in the Hudson Valley, but few are as magnificent as Castle Hotel & Spa. From one of the finest spots in the area, this imposing stone house views the Hudson River with majestic beauty. The estate belongs to Small Luxury Hotels of the World and has 31 guest rooms and suites.
The hotel offers exquisitely furnished guest rooms, first-rate views, a whirlpool, a 24-hour fitness facility, and well-maintained jogging trails. The hotel’s Equus eatery, which has been awarded four diamonds by AAA, is well known. One of the top spas in the area is the Sankara Spa. The Castle Hotel & Spa is the ideal starting point for travelers to Sleepy Hollow and the region around it to explore the town and other picturesque tourist destinations along the Hudson River Valley.
#13. Take a Photo at the Headless Horseman Sculpture
You can also enjoy the Headless Horseman mythology while you’re in town by visiting the sculpture of the figure. This sculpture, by artist Linda Perlmutter, stands 18 feet tall and is located opposite Philipsburg Manor. A surrealist horseman is visible in the sculpture chasing after an equally terrifying Ichabod Crane. A particular wash was applied to the steel structure to enable oxidation, which produced the burned orange, Halloween-like hue.
#14. Astonish yourself with the Armour-Stiner Octagon House
The Armour-Stiner Octagon House is a must-see if you enjoy distinctive architecture. It was constructed after Donato Bramante’s 1502 Tempietto in Rome, one of the few entirely dome-covered octagonal homes in the entire globe. Although you can schedule certain tours in advance, the house is currently private property. You can still visit and take some pictures, though. It’s quite interesting to see. Joseph Stiner, a tea trader from New York City, built it in the 19th century.
The National Trust for Historic Preservation purchased the home in 1976, and in 1978 it sold it to a preservation architect. The building has been refurbished to its original 1872 condition, down to the furnishings and decorations.
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#15. Enjoy Yourself at the Annual Great Jack O’Lantern Blaze
The Great Jack O’Lantern Blaze is a yearly celebration that lights up the world with hundreds of blazing Jack O’Lanterns in Sleepy Hollow, Westchester County. In contrast to the old 18th-century structures, the festivities are held at Van Cortlandt Manor, where 7,000 hand-carved pumpkins emit warm candle glows. The Pumpkin Planetarium, the Pumpkin Windmill, and other events are held in the Museum of Pumpkin Art. Getting into Halloween and autumnal spirit is one of the coolest things to do in Sleepy Hollow in the fall.
What Is Sleepy Hollow Famous for?
Washington Irving, who resided in Tarrytown and is interred in Sleepy Hollow Cemetery, wrote “The Legend of Sleepy Hollow” in 1820, short fiction about the community and its fabled phantom, the Headless Horseman. This story made the village famous throughout the world.
Is Sleepy Hollow Worth Visiting?
This is a fantastic destination and historic Dutch settlement that is amazing to visit any time of year. Thoughfall is a particularly popular time due to the Sleepy Hollow folklore that is connected to Irving’s literary classic, which is regarded as one of the first well-known works of American literature.
How Scary is Sleepy Hollow?
This is an extremely graphic film with dozens of headless bodies, spurting blood, severed heads that fly to the ground, more murders, and, of course, characters who are constantly in danger.