5 Things To Do In Sleepy Hollow NY In October for Halloween

A drowsy, dreamy influence seems to hang over the land, and to pervade the very atmosphere. Some say that the place was bewitched by a high German doctor, during the early days of the settlement…”

-Washington Irving, The Legend of Sleepy Hollow




While the town of Sleepy Hollow is well-known as the place that the Headless Horseman haunts in Washington Irving’s The Legend of Sleepy Hollow, it has stayed relatively hidden that the town actually exits until more recently. Even though there have been Sleepy Hollow films, such as Tim Burton’s 1999 film that stared Johnny Depp and Christina Ricci, it’s commonly thought that the town was simply part of the fictional tale. The exception usually lies in the literary die-hards who have studied Irving’s life outside of his works.

This common misconception changed in 2013 with the release of FOX’s drama series Sleepy Hollow. The television series took place in the town of Sleepy Hollow, NY. This resultantly peaked interest in the small town, putting it on the map. Sleepy Hollow, NY and it’s adjoining town Tarrytown, NY are filled of rich history, dating back to the 1600s. While their Halloween happenings may not yet be as sophisticated as Salem’s Haunted Happenings, there are plenty of spooky things to do throughout October. You’ll find that many Sleepy Hollow October events don’t take place directly in Sleepy Hollow. Rather, they are spread out throughout the Historic Hudson Valley area, better known as “Sleepy Hollow Country” during Halloween time.

1\ Sleepy Hollow Cemetery, Old Dutch Burying Ground, and Old Dutch Church of Sleepy Hollow

Headless Horseman Sleepy Hollow Cemetery

It’s not a Sleepy Hollow visit without stopping by the final resting place of Washington Irving and the key points of interest from his Legend of Sleepy Hollow story.

Sleepy Hollow Cemetery was incorporated in 1849 as Tarrytown Cemetery, but posthumously honored Irving’s request that it change its name to Sleepy Hollow Cemetery. This is where the famous Sleepy Hollow author is buried.

Irving’s famous Sleepy Hollow story takes place in the area right next to Sleepy Hollow Cemetery, the Old Dutch Burying Ground and Old Dutch Church of Sleepy Hollow. Founded around 1685, this is the church and churchyard that appear in Irving’s story. While the churchyard is often confused with the adjacent Sleepy Hollow Cemetery, they are technically separate. Luckily, since they are right next to each other, visiting both sites couldn’t be easier.

You can take self-guided tours of both areas. The Sleepy Hollow Cemetery also holds special events, including daytime and evening guided tours (including ghost tours). The Old Dutch Church also usually holds special events (one is listed next). During normal business hours, keep your eyes pealed for the Headless Horseman on his trusty steed creeping around the grounds!

The Sleepy Hollow Cemetery is located at 540 North Broadway, Sleepy Hollow. The Old Dutch Burying Ground and Church address is 430 North Broadway, Sleepy Hollow.

2\ Irving’s “Legend”

For a unique Sleepy Hollow experience, head over to Irving’s “Legend.”┬áMaster storyteller Jonathan Kruk gives a dramatic performance of Washington Irving’s classic tale, The Legend of Sleepy Hollow, at this event. The performance is accompanied by live spooky organ music by Jim Keyes. It doesn’t get more Halloween-y than hearing the Sleepy Hollow story in the churchyard where it took place! The performance lasts about 45 minutes.

3\The Great Jack O’Lantern Blaze at Van Cortlandt Manor

Only a short drive away from Sleepy Hollow and Tarrytown is The Great Jack O’Lantern Blaze at the Van Cortlandt Manor. It’s one of the tri-state area’s biggest fall events. During the walk-through experience that’s located at a historic 18th century manor, meander through more than 10,000 individually hand-carved, illuminated jack o’lanterns.

The Great Jack O’Lantern Blaze at Van Cortlandt Manor is located at 525 S Riverside Avenue, Croton-on-Hudson, NY. Tickets for this event sell out fast, so plan ahead. Luckily, The Great Jack O’Lantern Blaze runs through November, so it can be a fun way to celebrate Thanksgiving, too.

4\ Sunnyside: Home of the “Legend”

Washington Irving Sunnyside Home

Sunnyside in Irvington, NY was Washington Irving’s riverside home. During October, Sunnyside celebrates its connection to Irving’s classic tale, The Legend of Sleepy Hollow. It’s a daytime event, where you can tour Irving’s home, hear stories about what inspired him to write the famous short story, and see works of art inspired by the story. Since it’s a daytime event, it’s a great lead-in to the evening events around the area.

Sunnyside is located at 3 W Sunnyside Lane, Irvington, NY.

5\ Horseman’s Hollow

For a good old fashion Halloween scare, skulk over to Horseman’s Hollow. Just like many other “Sleepy Hollow Country” events, this haunted house takes place at a historic site, Philipsburg Manor. Horseman’s Hollow takes The Legend of Sleepy Hollow to its darkest extremes, transforming Philipsburg Manor into, “a terrifying landscape ruled by the undead, the evil, and the insane.”

Horseman’s Hollow at Philipsburg Manor is located at 100 Continental Street in Sleepy Hollow.