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Sleepy Hollow is a village in the town of Mount Pleasant, New York, United States. The village is located on the east bank of the Hudson River, about 20 miles (32 km) north of New York City, and is served by the Philipse Manor stop on the Metro-North Hudson Line.
Plan your visit to Sleepy Hollow with our calendar of events. From Halloween classics to new attractions, there's something for everyone!
- Visit The Sleepy Hollow Cemetery. 540 N Broadway. If you’re looking for unique things to do in Sleepy Hollow, NY, make sure to add a visit to Sleepy Hollow Cemetery on your list.
- Take A Guided Ghost Tour. While many would think to go right to the famous cemetery for a ghost tour, it’s actually the Tarrytown Music Hall that does actual paranormal investigations!
- The Old Dutch Church. 430 North Broadway. Check out the Old Dutch Church, one of the oldest surviving churches in New York, with its gothic architecture and eerie cemetery.
- Discover Philipsburg Manor. 381 North Broadway. A restored 18th-century farm and mill, where you can learn about life in Colonial America. The modern-day settlements of Sleepy Hollow and Tarrytown are offspring of Philipsburg Manor, an agricultural, milling, and commerce hub from the colonial era.
Sleepy Hollow (estimated population of 11,000) is a charming and historic village in New York State’s Hudson Valley. The ghostly village is best known as the setting of Washington Irving’s “The Legend of Sleepy Hollow.”
- Legendary Things to Do in Sleepy Hollow
- Things to Do in Tarrytown & Nearby
- Where to Stay in Tarrytown & Sleepy Hollow
- Getting to Sleepy Hollow & Tarrytown NY
- What to Do in Sleepy Hollow & Tarrytown (Post Summary)
Wander Around Sleepy Hollow
Whether you’re visiting during the Halloween season or not, one of the best things to do in Sleepy Hollow is explore the charming downtown area anytime of the year. During the Halloween season and month of October, the entire downtown is decked out with spooky decor and feels straight out of a Halloween movie! Begin your journey at Beekman Avenue near Broadway, the heart of Sleepy Hollow’s downtown. During Halloween, you’ll encounter eerie decorations at the Sleepy Hollow clock. Take a leisur...
Sleepy Hollow Lighthouse & Scenic Hudson Riverwalk
Another one of the best things to do in Sleepy Hollow is enjoy a picturesque walk along the Scenic Hudson Riverwalk overlooking the Hudson Valley, Governor Mario Cuomo Bridge over the Hudson River, and the picturesque Sleepy Hollow Lighthouse. We are big fans of cute and gorgeous East Coast lighthouses, we don’t know why but we just are and this one doesn’t disappoint! The Sleepy Hollow Lighthouse is also often referred to as the Tarrytown Lighthouse or Kingsland Point Lighthouse as well. Thi...
Find the Headless Horseman Sculpture
One of the best Sleepy Hollow attractions and quick photo stop is the Headless Horseman sculpture located just outside the Sleepy Hollow cemetery and next to the famous bridge where it all happened! The 18-foot high sculpture is made out of metal and has a rusted appearance made by Miglo-Bufkin depicting the moment the Headless Horseman chased down Ichabod Crane on horseback and hurling a pumpkin at his head. Find this quick and fun thing to do in Sleepy Hollow and photo spot at 420 North Bro...
The Great Jack O’Lantern Blaze
Easily one of the most famous and best things to do near Sleepy Hollow, NY during autumn is The Great Jack O’Lantern Blaze! Each year in the fall, you can walk through more than 7,000 hand-carved jack o’ lanterns by artists that are illuminated making for an enchanting evening located around a 20-minute drive away at Croton-on-Hudson. Located at the 18th-century Van Cortlandt Manor you can enjoy this impressive display of pumpkins and jack o’ lanterns synched up to an original soundtrack! Oth...
Shops and Dining in Tarrytown
Don’t miss one of our favorite things to do in Tarrytown, explore the picturesque and quintessential downtown that looks straight out of a movie that’s been named one of the top 10 prettiest towns in America by Forbes. Don’t miss the gorgeous storefronts and buildings up and down the Main Street dotted with cute shops, restaurants, and cafes. One of the star attractions and best things to do in Tarrytown is check out a show the historic Tarrytown Music Hall. If you can’t catch a show, even ju...
Kykuit a Rockefeller Estate
Another must-see attraction and best thing to do in Tarrytown is visit Kykuit, the Rockefeller Estate located in the scenic Pocantico Hills. In 1913, John D. Rockefeller completed his family estate, making it one of a few famous estates still in the area today open for tours by one of the wealthiest men in American history. Since its completion in 1913, four generations of Rockefeller family members and descendants of the Standard Oil Company tycoon lived here and continuously added to this g...
While enjoying all the best things to do in Tarrytown and things to do in Sleepy Hollow can be easily enjoyed in a day trip from New York City, you can also easily make it into an overnight trip with a luxurious stay at the Castle Hotel & Spa an actual castle hotel overlooking the Hudson Valley in Tarrytown. You can find the Castle Hotel property p...
Getting to all the best things to do in Tarrytown, NY and Sleepy Hollow attractions couldn’t be easier since it’s located only around 30 miles north of Manhattan and easy to access on the Hudson Line train at Grand Central Station or Penn Station. Train trips take around 35 to 90 minutes from here and many of the best things to do in Sleepy Hollow ...
Explore Downtown Sleepy HollowSleepy Hollow Lighthouse & Scenic Hudson RiverwalkFind the Headless Horseman SculptureGo to the Headless Horseman BridgeOct 19, 2022 · How to Spend a Weekend Exploring Sleepy Hollow, New York's Stately Manors, Historic Cemeteries, and Stylish Restaurants. For fright and fun in spades, from the Headless Horseman to...
Nov 19, 2023 · Just a short train ride away from New York City is one of the cutest and best small towns in New York – Sleepy Hollow. It sits a mere 30 miles away from NYC and makes for one of the most epic of NYC day trips since there are a ton of fun things to do in Sleepy Hollow NY.
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