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.
Planning your first visit to Sleepy Hollow? Read our planning suggestions at A Perfect Fall Day in Sleepy Hollow.
What to see
There’s so much to do in Sleepy Hollow Country when the leaves turn color. Start planning your adventure here!
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.
Irving’s Legend
Master storyteller Jonathan Kruk casts a spell with dramatic performances of the classic tale!
The Headless Horseman Files
Four suspects, one missing schoolmaster, and you must solve the case!
Tarrytown Music Hall Ghost Tours
Spirits linger in this picturesque Victorian era theatre!
Sleepy Hollow Street Fair
Food, music, local retailers, arts & crafts, plus Halloween and Holiday items!
SUP Witches Festival
Once a year, the water off Sleepy Hollow fills with witches and warlocks on stand-up paddleboards!
Tarrytown Halloween Parade
24th annual parade followed by block party!
Sleepy Hollow Haunted Hayride
Climb aboard Sleepy Hollow’s annual Haunted Hayride and hold on to your head!
Glass Pumpkin Patch Fundraiser
This festive event features hundreds of whimsical, vibrantly colored glass pumpkins. These one-of-a-kind works of art will be available for …
Octagon House Myths and Mysteries Tour
18 miles north of New York City, high on a bank along The Hudson River sits The Armour-Stiner (Octagon) House. Built in 1860, this …
Paint a Headless Horseman with Heather Gleason
Join Halloween artist Heather Gleason as she teaches you the step-by-step process of painting your own Headless Horseman Painting! Each …
An Audience with Poe
Sip, savor, and shiver with Poe’s darkest tales brought to life!
The Spirits of Sleepy Hollow Country
Once thought long departed, these spirits are still present and have quite a bit to say!
Sleepy Hollow Oktoberfest
German food and beer, live Bavarian music, and the Hudson at your back — Sleepy Hollow’s Oktoberfest returns for its 14th year. Local …
Twilight Village at Sleepy Hollow
An evening filled with folklore, fortune-telling, spooky entertainment and a Halloween night market.
Historical Society
The Historical Society has been the keeper of the collective memories of the villages of Sleepy Hollow and Tarrytown since 1889!
More places for a fall day
Where to see the Headless Horseman
The Horseman turns up in more than a dozen places across the season. See our guide to where to see the Headless Horseman. He’s not tame, so no guarantees, but here are the major events where he has been known to appear:
The schedule
We do our best to keep the Sleepy Hollow Halloween calendar up-to-date, but to avoid disappointment you should contact establishments in advance to confirm hours of operation, rates, and availability.
