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- Village of Sleepy Hollow
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Immortalized in Washington Irving’s famous tale, “The Legend of Sleepy Hollow”, the real Sleepy Hollow is now a modern village that is home to a diverse population of nearly 10,000 residents. It is located 25 miles north of New York City on the eastern shore of the Hudson River, in Westchester County.
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Sleepy Hollow Sprint Triathlon
Kingsland Point Park299 Palmer Avenue, Sleepy Hollow, NY, United StatesA half-mile swim in the Hudson River,11-mile scenic bike ride through the legendary village,3-mile run along Hudson River Walk. All proceeds of the Sleepy Hollow Sprint Triathlon will benefit the Village of Sleepy Hollow Recreation Department’s Teen Summer Camp. The underlying goal of the summer day camp is to provide the children of the community …
$145 – $200
Sleepy Hollow Mermaid Festival
Kingsland Point Park299 Palmer Avenue, Sleepy Hollow, NY, United StatesParticipate in the area’s first ever land and water parade! March through the park in costume or float on stand up paddle boards and kayaks on the Hudson. After the parade there will be music, bounce houses, face painting, and food trucks in Kingsland Point Park along with fun art, history, and beach activities from …
Free
Event SeriesJazz at Horan’s Landing
Jazz at Horan’s Landing
Horan's Landing Park57 River Street, Sleepy Hollow, NY, United StatesEnjoy four free Tuesday evenings of Jazz at Sleepy Hollow's waterfront Horan's Landing Park! This August Mark Morganelli & The Jazz Forum All-Stars Celebrate Brasil! Featuring Eddie Monteiro, Roni Ben-Hur & Nanny Assis. Bring a picnic dinner or enjoy local food truck fare while watching the sun set over the Hudson River. 2024 Schedule: Tuesdays, …
Free
Event SeriesJazz at Horan’s Landing
Jazz at Horan’s Landing
Horan's Landing Park57 River Street, Sleepy Hollow, NY, United StatesEnjoy four free Tuesday evenings of Jazz at Sleepy Hollow's waterfront Horan's Landing Park! This August Mark Morganelli & The Jazz Forum All-Stars Celebrate Brasil! Featuring Eddie Monteiro, Roni Ben-Hur & Nanny Assis. Bring a picnic dinner or enjoy local food truck fare while watching the sun set over the Hudson River. 2024 Schedule: Tuesdays, …
Free
Event SeriesJazz at Horan’s Landing
Jazz at Horan’s Landing
Horan's Landing Park57 River Street, Sleepy Hollow, NY, United StatesEnjoy four free Tuesday evenings of Jazz at Sleepy Hollow's waterfront Horan's Landing Park! This August Mark Morganelli & The Jazz Forum All-Stars Celebrate Brasil! Featuring Eddie Monteiro, Roni Ben-Hur & Nanny Assis. Bring a picnic dinner or enjoy local food truck fare while watching the sun set over the Hudson River. 2024 Schedule: Tuesdays, …
Free
Event SeriesJazz at Horan’s Landing
Jazz at Horan’s Landing
Horan's Landing Park57 River Street, Sleepy Hollow, NY, United StatesEnjoy four free Tuesday evenings of Jazz at Sleepy Hollow's waterfront Horan's Landing Park! This August Mark Morganelli & The Jazz Forum All-Stars Celebrate Brasil! Featuring Eddie Monteiro, Roni Ben-Hur & Nanny Assis. Bring a picnic dinner or enjoy local food truck fare while watching the sun set over the Hudson River. 2024 Schedule: Tuesdays, …
Free
Oktoberfest
Kingsland Point Park299 Palmer Avenue, Sleepy Hollow, NY, United StatesFeast on German food and beer from local eateries and dance to live Bavarian music at Sleepy Hollow's annual Oktoberfest! Cider and hot chocolate is offered for the younger set, music and entertainment for all ages! Free to enter, parking is $5 per car.
Free
Sleepy Hollow Street Fair
Beekman Avenue, Sleepy HollowBeekman Avenue, Sleepy Hollow, NY, United StatesTheSleepy Hollow Tarrytown Chamber of Commerce’s annual Sleepy Hollow Street Fair takes place this year on Saturday, October 14th, transforming Beekman Avenue into a huge outdoor market. Nearly 100 vendors draw thousands of visitors! October is the most exciting time to visit Sleepy Hollow. The weeks leading up toHalloween have something for everyone: haunted hayrides, …
Free
SUP Witches of Sleepy Hollow Festival
Horan's Landing Park57 River Street, Sleepy Hollow, NY, United StatesSearching for a wicked sight? Come to Horan’s Landing Waterfront Park for the 5th Annual SUP Witch Paddle where the witches gather and “The Legend of Sleepy Hollow” is told. Join the witches on the water or stroll along the Riverwalk and watch the witches pass by. Vendors, food, brews & spooky views! A memorable …
Free
FeaturedEvent SeriesSleepy Hollow Haunted Hayride
Sleepy Hollow Haunted Hayride
Sleepy Hollow Village Hall28 Beekman Avenue, Sleepy Hollow, NY, United StatesClimbaboard Sleepy Hollow’s annual Haunted Hayride and hold on to your head! All seems well when you board your hay wagon in the brightly lit streets ofdowntownSleepy Hollow. Rumbling off into the dark you realize too late you are headingdown the Albany Post Road past the Old Dutch Church, following exactly Ichabod Crane’s flight from …
FeaturedEvent SeriesSleepy Hollow Haunted Hayride
Sleepy Hollow Haunted Hayride
Sleepy Hollow Village Hall28 Beekman Avenue, Sleepy Hollow, NY, United StatesClimbaboard Sleepy Hollow’s annual Haunted Hayride and hold on to your head! All seems well when you board your hay wagon in the brightly lit streets ofdowntownSleepy Hollow. Rumbling off into the dark you realize too late you are headingdown the Albany Post Road past the Old Dutch Church, following exactly Ichabod Crane’s flight from …
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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.
