Rocky’s 5k
Beautiful fall foliage is the perfect backdrop for Rocky’s 5K. Challenging hills and wide carriage roads – the perfect race for experienced trails runners and first timers. If you are familiar …
$25 – $45
25 events found.
Sponsored
Outdoors
Events
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Rockefeller State Park Preserve 125 Phelps Way, Pleasantville, NY, United States
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Classic Daytime Cemetery Tour
Sleepy Hollow Cemetery South Gate 430 North Broadway, Sleepy Hollow, NY, United StatesSoak up the beauty of this 176-year old cemetery while your guide regales you with stories of the fascinating people resting here in peace. This two-hour daytime walk is the perfect …
$30 -
The Original Knickerbocker Tour
Sleepy Hollow Cemetery South Gate 430 North Broadway, Sleepy Hollow, NY, United StatesThe Original Knickerbocker: Washington Irving & “The Legend of Sleepy Hollow”. Meet the father of the American short story on this one-hour tour of Sleepy Hollow Cemetery! Learn all about …
$20 -
The Headless Horseman Files
Philipsburg Manor 381 North Broadway, Sleepy Hollow, NY, United StatesImmerse yourself in this Sleepy Hollow whodunit and decide for yourself what really happened to Ichabod Crane. Follow your guide on a mysterious 45-minute walk through the historic grounds of …
$25 – $30 -
The Original Knickerbocker Tour
Sleepy Hollow Cemetery South Gate 430 North Broadway, Sleepy Hollow, NY, United StatesThe Original Knickerbocker: Washington Irving & “The Legend of Sleepy Hollow”. Meet the father of the American short story on this one-hour tour of Sleepy Hollow Cemetery! Learn all about …
$20 -
Classic Daytime Cemetery Tour
Sleepy Hollow Cemetery South Gate 430 North Broadway, Sleepy Hollow, NY, United StatesSoak up the beauty of this 176-year old cemetery while your guide regales you with stories of the fascinating people resting here in peace. This two-hour daytime walk is the perfect …
$30 -
The Original Knickerbocker Tour
Sleepy Hollow Cemetery South Gate 430 North Broadway, Sleepy Hollow, NY, United StatesThe Original Knickerbocker: Washington Irving & “The Legend of Sleepy Hollow”. Meet the father of the American short story on this one-hour tour of Sleepy Hollow Cemetery! Learn all about …
$20 -
The Great Jack O’Lantern Blaze
Van Cortlandt Manor 525 S Riverside Avenue, Croton-on-Hudson, NY, United StatesBigger, Brighter, and More Spectacular Than Ever Before! The Great Jack O'Lantern Blaze is the Hudson Valley’s most electrifying fall happening! Meander through the 18th-century landscape of Van Cortlandt Manor …
$24 – $50 -
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! As evening settles over Philipsburg Manor, channel the spirit of Irving’s famously creepy tale at this immersive outdoor experience with live storytellers, fire performers, …
$25 – $30 -
Sleepy Hollow Cemetery Lantern Tour
Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow, NY, United StatesStep back in time and explore the cemetery by kerosene lantern light! This two-hour evening tour gives you a great overview of why Sleepy Hollow Cemetery is so famous. You’ll …
$50 -
The Good, the Bad and the Unusual-Cemetery Tour
Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow, NY, United StatesJoin Sara Mascia and Tara Van Tassell from our local historical society as they dish about several intriguing locals as well as some of Sleepy Hollow Cemetery's world-famous inhabitants. You …
$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 the cemetery by kerosene lantern light! This two-hour evening tour gives you a great overview of why Sleepy Hollow Cemetery is so famous. You’ll …
$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 is fresh …
Free -
Walk for Wishes: A Sleepy Hollow Family Fun Fall Festival
Kingsland Point Park 299 Palmer Avenue, Sleepy Hollow, NY, United StatesWalk for Wishes: A Sleepy Hollow Family Fun Fall Festival returns on October 5, 2025, from 9am-2pm at Kingsland Point Park, bringing a heartwarming, Halloween-themed celebration for all ages to …
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Classic Daytime Cemetery Tour
Sleepy Hollow Cemetery South Gate 430 North Broadway, Sleepy Hollow, NY, United StatesSoak up the beauty of this 176-year old cemetery while your guide regales you with stories of the fascinating people resting here in peace. This two-hour daytime walk is the perfect …
$30 -
The Original Knickerbocker Tour
Sleepy Hollow Cemetery South Gate 430 North Broadway, Sleepy Hollow, NY, United StatesThe Original Knickerbocker: Washington Irving & “The Legend of Sleepy Hollow”. Meet the father of the American short story on this one-hour tour of Sleepy Hollow Cemetery! Learn all about …
$20 -
The Headless Horseman Files
Philipsburg Manor 381 North Broadway, Sleepy Hollow, NY, United StatesImmerse yourself in this Sleepy Hollow whodunit and decide for yourself what really happened to Ichabod Crane. Follow your guide on a mysterious 45-minute walk through the historic grounds of …
$25 – $30 -
The Original Knickerbocker Tour
Sleepy Hollow Cemetery South Gate 430 North Broadway, Sleepy Hollow, NY, United StatesThe Original Knickerbocker: Washington Irving & “The Legend of Sleepy Hollow”. Meet the father of the American short story on this one-hour tour of Sleepy Hollow Cemetery! Learn all about …
$20 -
Classic Daytime Cemetery Tour
Sleepy Hollow Cemetery South Gate 430 North Broadway, Sleepy Hollow, NY, United StatesSoak up the beauty of this 176-year old cemetery while your guide regales you with stories of the fascinating people resting here in peace. This two-hour daytime walk is the perfect …
$30 -
The Original Knickerbocker Tour
Sleepy Hollow Cemetery South Gate 430 North Broadway, Sleepy Hollow, NY, United StatesThe Original Knickerbocker: Washington Irving & “The Legend of Sleepy Hollow”. Meet the father of the American short story on this one-hour tour of Sleepy Hollow Cemetery! Learn all about …
$20 -
Blessing of the Animals
Christ Church San Marcos 43 South Broadway, Tarrytown, NY, United StatesBlessing of the Animals brings together furry friends, fish & fowl, snakes, bugs, zebras & elephants. Pets and people of all faiths, and no faith, are welcome! The Blessing takes …
Free -
The Great Jack O’Lantern Blaze
Van Cortlandt Manor 525 S Riverside Avenue, Croton-on-Hudson, NY, United StatesBigger, Brighter, and More Spectacular Than Ever Before! The Great Jack O'Lantern Blaze is the Hudson Valley’s most electrifying fall happening! Meander through the 18th-century landscape of Van Cortlandt Manor …
$24 – $50 -
Twilight Village at Sleepy Hollow
Philipsburg Manor 381 North Broadway, Sleepy Hollow, NY, United StatesWhere the Legend Lives After Dark! As evening settles over Philipsburg Manor, channel the spirit of Irving’s famously creepy tale at this immersive outdoor experience with live storytellers, fire performers, …
$25 – $30
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.