October in Sleepy Hollow
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!
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 Horsemen: Terror Lies in Chaos
Nights of terror return this Fall with a brand-new Sleepy Hollow haunted house!
Lyndhurst After Dark
There's nothing like a Gothic mansion after hours!
Headless Horseman Ball
A night of spine-tingling excitement at the Castle Hotel!
The Legend Cirque
Gravity-defying performance of The Legend of Sleepy Hollow!
Hulda's Night
Follow local legends into the night time woods of Rockefeller State Park!
Tarrytown Halloween Parade
21st annual parade followed by block party!
Music Hall Ghost Tours
Spirits linger in this picturesque Victorian era theatre!
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!
Spirits of Sleepy Hollow Country
Once thought long departed, these spirits are still present and have quite a bit to say!
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!
Sleepy Hollow Street Fair
Food, music, local retailers, arts & crafts, plus Halloween and Holiday items!
Historical Society Tours
Explore the history of Tarrytown and Sleepy Hollow!
Farmers Markets
Fresh Hudson Valley produce, meat, bread, cut flowers, dairy products, preserves, wine, and beer!
Where to see the Headless Horseman
One of the most frequent questions we get is "where can I see the Headless Horseman?" He's not tame, so no guarantees, but here are events where he has been known to appear:
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.