SUP Witches Festival
Hundreds of costumed witches, warlocks, and wizards paddle the Hudson River off Kingsland Point Park in one of Sleepy Hollow's signature Halloween traditions. On shore, "Witches Hollow" brings live music, …
$8 – $35
25 events found.
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Events
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Kingsland Point Park 299 Palmer Avenue, Sleepy Hollow, NY, United States
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The Original Knickerbocker Tour
Sleepy Hollow Cemetery South Gate 430 North Broadway, Sleepy Hollow, NY, United StatesThe Original Knickerbocker Tour: Washington Irving & "The Legend of Sleepy Hollow" Meet the father of the American short story on this one-hour walking tour through the south end of …
$20 -
Sleepy Hollow: Fact & Fiction with J.W. Ocker
Tarrytown Music Hall 13 Main Street, Tarrytown, NY, United StatesGet an exclusive glimpse into local folklore and history from popular podcaster and bestselling author J.W. Ocker, whose brand-new book, Chasing the Headless Horseman (Countryman Press, Sept. 2026), investigates how …
$35 -
An Audience with Poe
Historic Hudson Valley 639 Bedford Road, Tarrytown, United StatesSip, savor, and shiver with Poe’s darkest tales brought to life through storytelling, cocktails, and confections. Professional storytellers bring to life the “powerful graphic effect” that Washington Irving once praised …
$65 -
Spirits of Sleepy Hollow Country
Philipsburg Manor 381 North Broadway, Sleepy Hollow, NY, United StatesSleepy Hollow has more ghosts than the Horseman. Two illusionists intend to get them talking. Mark Clearview and Nick Wallace return to Philipsburg Manor this October with an original magic show built around the spirits …
$65 – $89 -
The Original Knickerbocker Tour
Sleepy Hollow Cemetery South Gate 430 North Broadway, Sleepy Hollow, NY, United StatesThe Original Knickerbocker Tour: Washington Irving & "The Legend of Sleepy Hollow" Meet the father of the American short story on this one-hour walking tour through the south end of …
$20 -
‘Tis the Wind and Nothing More
Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington, NY, United StatesAn immersive Halloween-season tour with a performance of "The Raven" at the Armour-Stiner Octagon House, Irvington, NY For two October weekends only, the Armour-Stiner Octagon House goes back more than …
$58 -
Irving’s Legend at Sunnyside
Sunnyside 3 W Sunnyside Lane, Irvington, NY, United StatesHear the Legend told on Washington Irving's own lawn. Washington Irving is buried a few miles up the road. Every October, his most famous story comes back to the house …
$40 – $45 -
‘Tis the Wind and Nothing More
Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington, NY, United StatesAn immersive Halloween-season tour with a performance of "The Raven" at the Armour-Stiner Octagon House, Irvington, NY For two October weekends only, the Armour-Stiner Octagon House goes back more than …
$58 -
The Great Jack O’Lantern Blaze
Van Cortlandt Manor 525 S Riverside Avenue, Croton-on-Hudson, NY, United StatesMore than 7,000 hand-carved jack o'lanterns light up the riverside grounds of Van Cortlandt Manor. Ten acres of an 18th-century estate above the Hudson become a half-mile walk past life-sized …
$24 – $189 -
Sleepy Hollow Fright Fest
Kusel Auditorium at Sleepy Hollow High School 210 North Broadway, Sleepy Hollow, NY, United StatesSleepy Hollow Cinema is launching the 1st year of a national short-film competition for young horror filmmakers — high schoolers and undergrads screened right here in the Halloween Capital of …
Free -
Dr. Jekyll and Mr. Hyde
Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow, NY, United StatesThe Strange Case of Dr. Jekyll and Mr. Hyde One man, two natures. The brilliant Dr. Henry Jekyll is convinced that the evil in man is a quality that can …
$45 -
Murder and Mayhem Walking Tour
Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow, NY, United StatesThe true stories on this two-hour lantern tour of Sleepy Hollow Cemetery are so grim, you just might have nightmares! Curious to learn about a family that lost 5 children …
$60 -
Twilight Village at Sleepy Hollow
Philipsburg Manor 381 North Broadway, Sleepy Hollow, NY, United StatesWhere the Legend Lives After Dark! Mix and mingle with storytellers, fire performers, and iconic Legends. Enjoy a roving brass band, a pop-up evening market, and much more. Expanded experiences, …
$25 – $35 -
The Legend of Sleepy Hollow at Old Dutch Church
Old Dutch Church 430 North Broadway, Sleepy Hollow, NY, United StatesDon’t miss your chance to experience "The Legend of Sleepy Hollow" in the heart of Sleepy Hollow! On October 10, 11, 17, 18, 24, and 25 at 7 p.m., the …
$40 -
Sleepy Hollow Cemetery Lantern Tour
Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow, NY, United StatesStep back in time and explore Sleepy Hollow Cemetery by kerosene lantern light. This two-hour evening walk is the perfect introduction to why these storied grounds are so famous—an atmospheric …
$50 -
Kevin Nealon
Tarrytown Music Hall 13 Main Street, Tarrytown, NY, United StatesEmmy and SAG-nominated actor, comedian, and author Kevin Nealon is best known for his nine-year stint as a cast member of NBC’s Saturday Night Live, and has received critical acclaim …
$46.50 – $63.50 -
Dr. Jekyll and Mr. Hyde
Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow, NY, United StatesThe Strange Case of Dr. Jekyll and Mr. Hyde One man, two natures. The brilliant Dr. Henry Jekyll is convinced that the evil in man is a quality that can …
$45 -
Murder and Mayhem Walking Tour
Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow, NY, United StatesThe true stories on this two-hour lantern tour of Sleepy Hollow Cemetery are so grim, you just might have nightmares! Curious to learn about a family that lost 5 children …
$60 -
Sleepy Hollow Cemetery Lantern Tour
Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow, NY, United StatesStep back in time and explore Sleepy Hollow Cemetery by kerosene lantern light. This two-hour evening walk is the perfect introduction to why these storied grounds are so famous—an atmospheric …
$50 -
Irvington Farmers Market
Main Street School 101 Main Street, Irvington, NY, United StatesEnjoy live music, river views and a laid-back setting at this small-town Sunday market showcasing the best of what the Hudson Valley has to offer. In season, there's fresh local …
Free -
TarryHollow: Sleepy Hollow, Irving and the Old Dutch Church
418 North Broadway 418 North Broadway, Sleepy Hollow, United StatesEmbark on a captivating journey through the rich history of Sleepy Hollow, where the echoes of colonial America come to life. Join our local historical society for a 90-minute immersive walking tour, …
$28 -
The Headless Horseman Files
Philipsburg Manor 381 North Broadway, Sleepy Hollow, NY, United StatesFour suspects, one missing schoolmaster, and 45 minutes to work out what happened — Sleepy Hollow's whodunit, staged in broad daylight. A guide walks you through the grounds of Philipsburg …
$25 – $35 -
Ghost Tours of Tarrytown Music Hall
Tarrytown Music Hall 13 Main Street, Tarrytown, NY, United StatesJoin this guided tour created by Master Storyteller Jonathan Kruk and discover the historic lore and spirits that linger at The Tarrytown Music Hall. The Tarrytown Music Hall was built in 1885 …
$29 -
The Original Knickerbocker Tour
Sleepy Hollow Cemetery South Gate 430 North Broadway, Sleepy Hollow, NY, United StatesThe Original Knickerbocker Tour: Washington Irving & "The Legend of Sleepy Hollow" Meet the father of the American short story on this one-hour walking tour through the south end of …
$20
There's something for everyone in Sleepy Hollow Country—farmers markets, live music, street fairs, historic homes, hiking trails, kayaking and boating on the Hudson River. Halloween season brings even more for the whole family—haunted hayrides, blazing pumpkins, costumed 10K run, Halloween parade, and of course, the Headless Horseman! For the latest on Fall events, visit our guide to Halloween in Sleepy Hollow.