It's the most wonderful time of the year!
About October
Halloween in Sleepy Hollow has something for everyone: haunted hayrides, Gothic mansions, blazing pumpkins, farmers markets, live music, street fairs, 5K run (costumes welcome!), Halloween parade, and of course, the Headless Horseman!
Venues usually announce October event schedules in August with ticket sales starting around September 1. The Great Jack O'Lantern Blaze usually offers early sales to its members and sometimes opens pre-sales to followers of its social media accounts: Historic Hudson Valley's Instagram and Facebook.
Most October events sell out, especially weekend time slots. We strongly recommend you buy tickets before arriving.
What to see
There's so much to do in Sleepy Hollow when the leaves turn color. Start planning your adventure here!
The Great Jack O’Lantern Blaze
More than 7,000 hand-carved, illuminated pumpkins set against the mysterious backdrop of 18th-century buildings!
Sleepy Hollow Cemetery Tours
Day and evening guided walking tours of this historic 90-acre cemetery.
The Legend - Cirque Theatre
Gravity-defying performance of The Legend of Sleepy Hollow!
Lyndhurst After Dark
There's nothing like a Gothic mansion after hours!
Farmers Markets
Fresh Hudson Valley produce, meat, bread, cut flowers, dairy products, preserves, wine, and beer!
Music Hall Ghost Tours
Spirits linger in this picturesque Victorian era theatre!
Washington Irving’s “The Devil and Tom Walker
A miser sells his soul to the devil in exchange for pirate treasure!
Tarrytown Halloween Parade
20th annual parade followed by block party!
Hulda's Night
Follow local legends into the night time woods of Rockefeller State Park!
Haunted Hayride
Climb aboard Sleepy Hollow’s annual Haunted Hayride and hold on to your head!
Octagon House Myths & Mysteries
Delve into the myths and mysteries of this eight-sided house!
Irving's Legend
Master storyteller Jonathan Kruk casts a spell with dramatic performances of the classic tale!
Home of the 'Legend'
Outdoor family fun on the grounds of Washington Irving’s estate!
Historical Society Tours
Explore the history of Tarrytown and Sleepy Hollow!
Hulda: The Other Legend of Sleepy Hollow
This one-woman show tells the story of Hulda of Bohemia.
Oktoberfest
Celebrate the season on the shore of the Hudson River. Food, beverages, family fun!
The Legends of The Legend of Sleepy Hollow
Hear haunting tales of the ghosts surrounding the Headless Horseman!
Sleepy Hollow Street Fair
Food, music, local retailers, arts & crafts, plus Halloween and Holiday items!
The schedule
We do our best to keep this calendar up-to-date, but to avoid disappointment you should contact establishments in advance to confirm hours of operation, rates, and availability.
Sleepy Hollow is a real place?
Yes! More than 200 years ago, author Washington Irving gave the name "Sleepy Hollow" to the valley of a local stream. The villages of Sleepy Hollow and Tarrytown are on the east bank of the Hudson River, about 15 miles north of New York City. It's easy to get here by car or train.
