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Halloween in Sleepy Hollow has something for everyone: haunted hayrides, Gothic mansions, blazing pumpkins, farmers markets, live music, street fairs, our famous Halloween 10K run (costumes welcome!), Halloween parade, and of course, the Headless Horseman!
- Tarrytown Halloween Parade
Parking in the Villages of Tarrytown and Sleepy Hollow will...
- Great Jack O'Lantern Blaze
The wildly popular Great Jack O’Lantern Blaze returns in...
- Tarrytown Halloween Parade
If you’re looking for the ultimate Halloween getaway, pack your bags, dust off your witch hats, and prepare to venture into the legend-filled village of Sleepy Hollow, New York. This place isn’t just any spooky town; it’s the home of the infamous Headless Horseman!
The wildly popular Great Jack O’Lantern Blaze returns in 2024, including Halloween night! It features over 7,000 hand-carved, illuminated pumpkins set against the mysterious backdrop of Van Cortlandt Manor’s 18th-century buildings and riverside landscape.
- The Legend of Sleepy Hollow Sculpture. Just at the entrance to Philipsburg Manor lies the Legend of Sleepy Hollow Sculpture; a 4-foot granite slab sculpted by Michael Gressel which depicts Ichabod Crane fleeing from The Headless Horseman on horseback.
- The Headless Horseman sculpture. The Headless Horseman sculpture is an iconic must-see site when visiting Sleepy Hollow! Located across the street from the Legend of Sleepy Hollow sculpture, in the Route 9 median between Old Dutch Church and Philipsburg Manor restoration, this spectacular 18-foot-tall rust-colored work of art was created by local artist Linda Perlmutter and depicts the famous Ichabod Crane being chased down by the legendary Headless Horseman.
- The Headless Horseman Bridge. Sadly, the bridge described in Irving’s "The Legend of Sleepy Hollow" does not exist, however, the location (where a newer, more modern bridge stands) has been marked with a plaque.
- Sleepy Hollow Cemetery. Sleepy Hollow Cemetery is the final resting place for the legendary Washington Irving, as well as a number of famous names like Elizabeth Arden, Andrew Carnegie, members of the Rockefeller family, and more.
- Not Running For 2021.
- Places to Stay in Sleepy Hollow.
- Places to Drink in Sleepy Hollow.
- People to follow.
The following experiences are unfortunately not running for the 2021 season, but I’ve included them for future visits to Sleepy Hollow.
To fully experience Sleepy Hollow, you’ll need to spend a few days there. I recommend booking your hotel well in advance if you plan to visit during the busy Halloween season!
And finally, you’ll likely want to check out some of the area’s breweries after a long day of exploring!
Want to know more about Sleepy Hollow and the neighboring areas and attractions? These are the places I turn to get excited about the upcoming season! Follow these accounts on social media:
Sep 24, 2021 · Whether you’re a local anticipating a favorite Halloween tradition or a visitor looking to experience Halloween in Sleepy Hollow Country for the first time, The Hudson Independent has you covered. Read below for all the tricks, treats and haunts in Sleepy Hollow, Tarrytown, Irvington, Dobbs Ferry and the surrounding area.
Oct 4, 2023 · As the leaves turn red and a crisp autumn chill fills the air, the town of Sleepy Hollow in New York transforms into a spooky, otherworldly realm, thanks to its legendary past and bewitching array of Halloween festivities.
