10 INTERESTING THINGS TO DO IN SLEEPY HOLLOW, NYC THIS WEEKEND

There are a lot of things to do in Sleepy Hollow, New York, every weekend throughout the year, including seeing ancient estates, enjoying leisurely summertime picnics in the park, taking part in Halloween’s spooky festivities under the lanterns, and reading Washington Irving’s The Legend of Sleepy Hollow. Should you have a fondness for history, cuisine, building design, and the outdoors, it ought to be on your itinerary.

Even after numerous visits, we always manage to find something fresh and engaging to do. There aren’t many quaint little American villages with as many attractions as Sleepy Hollow.

Interesting Things To Do In Sleepy Hollow, New York

You’ve come to the perfect spot if you’re looking for activities in Sleepy Hollow!

New York’s Sleepy Hollow is a fantastic destination for a weekend getaway from the city. Halloween enthusiasts have long found Sleepy Hollow to be a great destination to come during the eerie season.

Nevertheless, it is a great destination to visit all year, even if it excels at serving the Halloween crowd.

With so much to do in Sleepy Hollow, visitors of all ages will love its festivals, amazing landmarks, and seasonal activities. It should come as no surprise that it frequently has a large influx of visitors.

Now, if you’re searching for the lowdown on things to do in New York, you don’t need to search any further because we’ve found some of the best activities around.

#1. Tour the Old Dutch Church

Few people are aware that The Legend of Sleepy Hollow, a well-known story by Washington Irving, is based on a real location. The actual Sleepy Hollow of Irving’s day served as inspiration for his eerie tale of the Headless Horseman. The Old Dutch Church, the oldest surviving church in New York, was the actual location of inspiration.

The church located in the Sleepy Hollow Cemetery is really called the Old Dutch Church of Sleepy Hollow. It was established in 1685 and is still going strong today. The church received the designation of a National Historic Landmark in the 1960s.

#2. Fill Your Baskets at the Farmers Market

In this Hudson River community, the Tarrytown-Sleepy Hollow Farmers Market (TaSH) is an essential component. Every Saturday, the market is open in Patriots Park, which is situated where Tarrytown and Sleepy Hollow meet. They are practically next door; the two merge.

#3. Get Spooked at the Headless Horseman Bridge

In The Legend of Sleepy Hollow, Washington Irving describes a wooden bridge as the location of the Headless Horseman’s most frequent sightings. It turns out that Creepy Hollow’s bridge actually exists. Although the bridge itself is not the same as the one that crossed the Pocantico River on the grounds of Sleepy Hollow Cemetery when Washington Irving lived there, the position is comparable.

#4. Tour Washington Irving’s Sunnyside Home

Sunnyside is the historic home of novelist Washington Irving, who authored The Legend of Sleepy Hollow while residing there. It is technically located in Tarrytown.

In the 1960s, the structure received the designation of a National Historic Landmark. It was formerly a component of the Philipsburg Manor estate. Irving bought the Hudson Riverfront Dutch stone house, which had two rooms at the time, in 1835. From here, he constructed Spanish towers, gables, Gothic windows, and chimneys in the Tudor style. He helped with the grounds’ landscaping as well.

#5. Visit the Sleepy Hollow Lighthouse

There are several names for this historic site, but the Sleepy Hollow Lighthouse is also known as the Tarrytown Lighthouse and the Kingsland Point Lighthouse. Since its installation in 1883, the lighthouse has guarded the hazardous areas on the east bank of the Hudson River.

#6. Spot Chagall and Matisse

Were you aware that this sleepy Hudson River hamlet is among the best places to savor works of art by Marc Chagall and Henri Matisse? It’s no surprise that this Westchester County town is endowed with world-class art when its people are like the Rockefellers.

#7. Indulge at Castle Hotel & Spa

There are plenty of lovely hotels and spas in the Hudson Valley, but not many are as remarkable as the Castle Hotel & Spa. Perched on one of the highest points in the area, this grand stone manor radiates majestic beauty while offering a breathtaking view of the Hudson River. The estate is a member of Small Luxury Hotels of the World and has 31 guest rooms and suites.

#8. The Old Croton Aqueduct

A trip to the Old Croton Aqueduct is history aficionados’ favorite thing to do in Sleepy Hollow, New York.

Known as the earliest water system in New York, it is currently a 26-mile walking trail that passes through Tarrytown.

It’s a fantastic option for nature enthusiasts as well, providing breathtaking views and a nice insight inside both settlements.

#9. Lyndhurst Castle

Everyone loves a castle. Make sure to schedule a guided tour of Lyndhurst Castle if you want to explore the locations of some of your favorite vampire episodes.

This is a must-do activity for anyone who enjoys films and television in Sleepy Hollow, New York. This is the spot to satiate your inner architecture nerd, with a frightening exterior that has some fantastic gothic flair.

Best Places To Visit In Sleepy Hollow

The notoriety of Sleepy Hollow, New York, is unquestionably well-established. Centuries after Washington Irving immortalized the ancient Hudson River village in his novel The Legend of Sleepy Hallow, the community has continued to attract tourists.

Sleepy Hollow, New York, is a community that is situated on the banks of the Hudson River today. It offers breathtaking views, a bustling historic center, and a quaint family atmosphere that is typical of many small communities in the Hudson Valley.

But it is much more than just the backdrop to Washington Irving’s chilling story. Native American tribes and, subsequently, European farmers laid the foundation of its history. The town has become a cherished home for the New York State nobility, the Rockefeller family. Since a large portion of the neighborhood is protected territory, both inhabitants and tourists have plenty of opportunities to explore the hills that rise from the banks of the Hudson River.

#1. Sleepy Hollow Cemetery

First, let’s talk about this cemetery. The cemetery serves as a wonderful starting point for getting to know the community and is a key location in The Legend of Sleepy Hollow. Irving is interred in the cemetery, but be aware that his grave is fenced off, so don’t plan on getting too close. When you visit in October, the cemetery is probably crowded with young people dressed in costumes.

#2. Dutch Reform Church

The Legend of Sleepy Hollow also mentions the Dutch Reform Church, which was established circa 1685. In a desperate rush, Ichabod Crane wanted to reach the chapel before the headless horseman did. Nevertheless, the church has been open continuously since the late 1600s and has a thriving congregation. The church cemetery serves as its burial place. It closes the grounds at 4:30 p.m.

#3. Headless Horseman Bridge

The Headless Horseman Bridge in Sleepy Hollow is another must-see site. Consider making a diversion to the bridge if you’re strolling through the cemetery. There is no longer a bridge across the Pocantico River where Ichabod Crane tumbles off his horse. Even with its historical inaccuracies, this bridge is a charming location for a selfie or photo.

#4. Headless Horseman Sculpture

Take a few minutes to get a picture of the sculpture depicting the headless horseman. It serves as an illustration of the passage in Irving’s book where the headless horseman throws the pumpkin at Ichabod Crane. It is located directly across from the Philipsburg Manor on Route 9.

#5. Philipsburg Manor

Visit the Philipsburg Manor, which is located near the Hudson River and is mentioned in Irving’s novel as well. Carpenter Frederick Philipse arrived in the Hudson Valley in 1653. In the end, his family possessed over 50,000 acres in the Hudson Valley.

#6. Washington Irving’s Sunnyside Estate

A significant destination in Sleepy Hollow is Washington Irving’s Sunnyside Estate. In 1835, he purchased the two-room Dutch home and completely renovated it. Be sure to explore the grounds and take in the beautiful scenery. Experience what it would have been like to live Irving’s life with guides dressed in historical attire.

#7. Kykuit

Kykuit is a section of the Rockefeller State Park Preserve and was once Rockefeller’s mansion. It is a must-see, whether you enjoy art, architecture, gardens, landscapes, or simply witnessing how the wealthiest people lived. You could explore Kykuit’s grounds for nearly a whole day. Impressive sculptures and gardens Watch out for the dinner-passing table with the water floating in the center. There are guided tours offered from May 12 through November 12.

#8. Rockefeller State Park Preserve

Westchester County’s Rockefeller State Park Preserve is a great place for a picnic, a trek, or perhaps a horseback ride. It’s interesting to note that using a horse carriage is permitted as well, provided you get a permit from the Preserve Office (which costs money).

#9. Armour-Stiner (Octagon) House

Don’t forget to visit the Octagon House and snap a photo from the exterior. Although you can now reserve certain tours in advance, the property is still a private residence. The octagon home is distinct because it is an eight-gon. It resembles an old classical temple and was constructed in the 1860s. Both the inside and the outdoors are worthwhile viewings.

#10. The Union Church Of Pocantico Hills

We always make an effort to visit the Union Church of Pocantico Hills when we are in the Hudson Valley. Although it is officially located in Tarrytown, Sleepy Hollow is only a short distance away. We just had to include it because it’s such a hidden gem. The rose window was one of Henri Matisse’s final creations before he passed away.

Things to Do in Sleepy Hollow This Weekend

Sleepy Hollow is a fantastic weekend vacation spot with a moniker that appeals to everyone’s inner Halloween enthusiast. The village celebrates Halloween with weekly festivals, hayrides, and parades. Tarrytown, a neighbor, is home to author Washington Irving and is also the birthplace of the Headless Horseman. In addition, other year-round attractions in the area cater to different seasons.

Here are some suggestions for things to do this weekend in Sleepy Hollow:

#1. Visit Philipsburg Manor

Discover this historic landmark, which features a functioning gristmill and Manor House, and travel back in time. Particularly picturesque in the autumn.

#2. Explore Sleepy Hollow Cemetery

Take a guided tour of Washington Irving’s resting place, the renowned Sleepy Hollow Cemetery. It’s sometimes a very fascinating and unsettling vibe.

#3. Sunset at the Hudson River

To see a stunning sunset, choose a picturesque location near the Hudson River. You may see the fabled Headless Horseman, and it’s a peaceful experience.

#4. Hollow of Horseman

Visit Philipsburg Manor’s haunted house, Horseman’s Hollow, if you’re in the mood for some eerie fun. Just be ready for some exhilarating jump scares!

#5. Walking Tour of Historic Sleepy Hollow

Enjoy a stroll along Sleepy Hollow’s quaint streets. Admire the old-world architecture and perhaps stop by a neighborhood cafe for a treat or coffee.

#6. Dutch Old Church

See the Sleepy Hollow Old Dutch Church, which was built in the seventeenth century. The Headless Horseman mythology is connected to the evocative churchyard.

#7. The Music Hall at Tarrytown

To find out what live acts or activities Tarrytown Music Hall has scheduled for the weekend, see their schedule. This facility has a great history and has been wonderfully refurbished.

#8. Local Restaurants

Investigate the food scene in the area. Some excellent restaurants in Sleepy Hollow serve a wide range of cuisines. It’s a fantastic way to end your exploration day.

Is Sleepy Hollow worth a visit?

This is a fantastic place to visit, and the historic Dutch settlement is even more popular in the fall due to the legend surrounding Sleepy Hollow, which is connected to Washington Irving’s novel, which is regarded as one of the first widely read works of American literature.

What is Sleepy Hollow, NY, known for?

Washington Irving, a Tarrytown resident who is buried at Sleepy Hollow Cemetery, wrote “The Legend of Sleepy Hollow,” a short story published in 1820 about the neighborhood and its notorious phantom, the Headless Horseman. This story made the village famous throughout the world.

Is Sleepy Hollow a walkable town?

If you prefer walking and have time to spare, it’s a manageable walk from either train station to Sleepy Hollow’s downtown area and historic sights. You’ll almost definitely need a car of your own, a taxi, or ride-sharing if you stay in any of the nearby hotels or motels.

How Scary Is Sleepy Hollow?

This is an extremely graphic film with numerous headless bodies, copious amounts of blood gushing, severed heads that land on the ground, numerous additional homicides, a few “boo!”-style jump scares, and, of course, characters who are always in danger. Eventually, all of the heads will also appear.

Can they touch you at Sleepy Hollow?

We don’t even come into contact with you in the haunted house. We ask that you refrain from touching any of our actors or objects in exchange.

Summary

Make sure to fit as many of these ideas into your visit to Sleepy Hollow as you can—there are a ton of things to do there!

With any luck, this list of activities in Sleepy Hollow, New York, has been helpful and given you lots of inspiration for your vacation.