5 Spooky Sleepy Hollow Attractions for Halloween

The quaint, charming village of Sleepy Hollow along the Hudson River comes to life during the Halloween season. As the setting of Washington Irving’s classic, The Legend of Sleepy Hollow, the town has fully embraced this claim to fame. In 1996, residents even voted to officially change its name from North Tarrytown to Sleepy Hollow. Its rich history and 38-minute train ride to Grand Central make Sleepy Hollow a popular choice for commuters to call home, or visitors to take a day trip to explore. The following five attractions are sure to give you the right amount of fright to get you in the spirit of Halloween, and give you a taste of all that Sleepy Hollow has to offer.

Daytime Attractions

1. Washington Irving’s Home, Sunnyside

Washington Irving’s Home, Sunnyside
Credit: Karen M. Sharman

Visit Irving’s home, Sunnyside, where your tour guide, dressed in traditional mid-19th century clothes, will take you through the house which has many of the original furnishings from the 1800s. You’ll also hear stories of what inspired Irving to write The Legend of Sleepy Hollow. This tour is the perfect start to a day of spookiness.

2. Sleepy Hollow Cemetery Walking Tours

Sleepy Hollow Cemetery
Credit: Shutterstock

Set among rolling hills with views of the Hudson, a walking tour of Sleepy Hollow Cemetery offers a great overview of its history. The tour takes you by the final resting places of some of Westchester’s most famous historical residents such as Washington Irving, Andrew Carnegie and William Rockefeller. There are one or two hour tours and daytime or evening options.

Nighttime Attractions

3. Live Performance of Irving’s The Legend of Sleepy Hollow

Historic Old Dutch Church, Sleepy Hollow
Credit: Jennifer Mitchell

Experience The Legend of Sleepy Hollow in a dramatic performance by master storyteller Jonathan Kruk. This event takes place at the historic Old Dutch Church and lasts about 45 minutes. Advanced tickets are required and it does sell out, so purchase your tickets ahead of time.

4. Horseman’s Hollow

Philipsburg Manor; Credit: Photo Tom Nycz

The Horseman’s Hollow is not for the faint of heart. Sleepy Hollow’s premier haunted attraction, it brings The Legend of Sleepy Hollow to life. Philipsburg Manor transforms into a haunted town driven mad by the Headless Horseman. Visitors walk through the terrifying scene, while the Hollow’s undead inhabitants lurk around every bend. The trail ends at Ichabod’s Schoolhouse, a twisting maze of horrors, delivering visitors at the lair of the Horseman. Buy tickets ahead of time as most nights sell out.

5. The Great Jack O’Lantern Blaze

Credit: Jennifer Mitchell

Nothing signifies Halloween season more than a jack o’lantern. And The Great Jack O’Lantern Blaze takes these carved pumpkins to the next level. Hundreds of intricately hand-carved and illuminated gourds mesmerize visitors. See jack o’lanterns used in creative ways to form everything from a T-Rex to a 20-foot-diameter pumpkin carousel. The event runs on select evenings through November 25.

Whether you already reside in the area, or are looking to explore Westchester’s Hudson River towns, the fall season is a great time to get out and experience Sleepy Hollow for yourself.

Find your home in or around Sleepy Hollow to take part in it’s rich history and traditions.


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