For the 50+ Traveler

We all know the story of the Headless Horseman, but how well do we know the place that inspired the infamous tale?

Sleepy Hollow is a real small town in Westchester County, New York, about 30 miles north of New York City. The area is known for its connection to the gothic piece of literature The Legend of Sleepy Hollow by Washington Irving.

Because of the area’s interesting literary history, Sleepy Hollow is known for going all out during October. We compiled a list of everything fun to do this October in Sleepy Hollow. Follow along below to learn more about the fun (and scares!) waiting for you there!

The Jack O'Lantern maze in Sleepy Hollow.

1. You Can Walk Through A Maze Of Jack O’Lanterns

October 3-31; November 1-3, 8-10, 15-17, 22-23, 29-30

Sleepy Hollow’s Great Jack O’Lantern Blaze is spooky fun for all ages!

Take the family for a stroll through a maze of over 7,000 jack o’lanterns that are hand-carved and carefully designed. On your walk, you’ll pass an enormous 25-foot-tall jack o’lantern Statue of Liberty as well as an impressive pumpkin windmill. Then, go for a joyride on the pumpkin carousel and stroll through the brand-new Museum of Pumpkin Art (we’re just as curious as you are).

The magic happens thanks to 1,000 volunteers who hand-select, scoop, carve, and light all the pumpkins you will see there! The Great Jack O’Lantern Blaze is the most popular Sleepy Hollow celebration of the season -- buy tickets ahead of time so you won’t miss out!

2. There’s A Spooky Silent Film Showing

October 4-6, 11-14, 18-20, 25-27, 31; November 1-3

The Unsilent Picture is based on The Adventure of the Mysterious Picture -- another eerie story by none other than Washington Irving.

The performance is said to “bend reality in the true spirit of Sleepy Hollow” as science and the paranormal meet face-to-face. The silent film features Tony Award-winner Bill Irwin. The creepy film is made all the creepier by live sound effects that are sure to make your hair stand on end. You can buy your tickets in advance here.

Zombies at Horseman's Hollow.

3. There Are Creepy Haunted Attractions

October 4-6, 11-13, 18-20, 25-27, 31; November 1-3

Ready for a good old-fashioned scare? Head to Horseman’s Hollow, which is known as Sleepy Hollow’s top spooky attraction!

As you walk through an 18th-century village said to have been ravaged by the Headless Horseman, you’ll see spooky landmarks like a cemetery, a tavern, and an ancient-looking church.

Look out for the Headless Horsemen himself -- and other undead lurking around the area. Tickets can be purchased here.

4. You Can Get Into An Immersive Theatrical Performance...

October 4-6, 10-13, 17-20, 24-27, 31; November 1-3

At the Sleepy Hollow Experience, you will quite literally walk through the Legend of Sleepy Hollow.

Follow your favorite characters -- Ichabod Crane, Katrina Van Tassel, and even the Headless Horseman -- from scene to scene while enjoying drinks and treats. This is an iconic Sleepy Hollow experience, so be sure to buy your tickets in advance!

A performance of The Legend Of Sleepy Hollow.

5. ...Or Sit Back And Enjoy A Play

October 4-6, 11-14, 18-20, 25-27, 31; November 1-3

If you’re pining for a more relaxed encounter with the Headless Horseman, consider treating yourself to tickets for the dramatic retelling of The Legend of Sleepy Hollow in the town’s Old Dutch Church. While there, you’ll enjoy performances by folks who step into character, plus live music.

6. Washington Irving’s Home Welcomes Visitors

October 5-6, 12-14, 19-20, 26-27; November 2-3

When you visit Washington Irving’s home, you’ll be invited to revisit some of the stranger parts of 19th-century history (think vampire scares) and learn about how The Legend of Sleepy Hollow has shaped popular culture through the years. You can also participate in a literature-themed scavenger hunt, historic games, and photo opportunities.

After getting your fill of the legends of Sleepy Hollow, head northeast to the Halloween capital of the world. Here’s why October is the best time of year to visit Salem, Massachusetts.