Sleepy Hollow Sprint Triathlon

Kingsland Point Park 299 Palmer Avenue, Sleepy Hollow, NY

A 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 13th 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 …

$135 – $185

Recurring

Jazz at Horan’s Landing

Horan's Landing Park 57 River Street, Sleepy Hollow, NY

Enjoy four free Tuesday evenings of Jazz at Sleepy Hollow's waterfront Horan's Landing Park with Mark Morganelli & The Jazz Forum All-Stars! Flugelhornist Mark Morganelli, with featured artists Eddie Monteiro and Nanny Assis, presents contemporary interpretations of Brazilian classics. Bring a picnic dinner or enjoy local food truck fare while watching the sun set over the …

Free
Recurring

Jazz at Horan’s Landing

Horan's Landing Park 57 River Street, Sleepy Hollow, NY

Enjoy four free Tuesday evenings of Jazz at Sleepy Hollow's waterfront Horan's Landing Park with Mark Morganelli & The Jazz Forum All-Stars! Flugelhornist Mark Morganelli, with featured artists Eddie Monteiro and Nanny Assis, presents contemporary interpretations of Brazilian classics. Bring a picnic dinner or enjoy local food truck fare while watching the sun set over the …

Free
Recurring

Jazz at Horan’s Landing

Horan's Landing Park 57 River Street, Sleepy Hollow, NY

Enjoy four free Tuesday evenings of Jazz at Sleepy Hollow's waterfront Horan's Landing Park with Mark Morganelli & The Jazz Forum All-Stars! Flugelhornist Mark Morganelli, with featured artists Eddie Monteiro and Nanny Assis, presents contemporary interpretations of Brazilian classics. Bring a picnic dinner or enjoy local food truck fare while watching the sun set over the …

Free
Recurring

Jazz at Horan’s Landing

Horan's Landing Park 57 River Street, Sleepy Hollow, NY

Enjoy four free Tuesday evenings of Jazz at Sleepy Hollow's waterfront Horan's Landing Park with Mark Morganelli & The Jazz Forum All-Stars! Flugelhornist Mark Morganelli, with featured artists Eddie Monteiro and Nanny Assis, presents contemporary interpretations of Brazilian classics. Bring a picnic dinner or enjoy local food truck fare while watching the sun set over the …

Free
Recurring

Jazz at Horan’s Landing

Horan's Landing Park 57 River Street, Sleepy Hollow, NY

Enjoy four free Tuesday evenings of Jazz at Sleepy Hollow's waterfront Horan's Landing Park with Mark Morganelli & The Jazz Forum All-Stars! Flugelhornist Mark Morganelli, with featured artists Eddie Monteiro and Nanny Assis, presents contemporary interpretations of Brazilian classics. Bring a picnic dinner or enjoy local food truck fare while watching the sun set over the …

Free

Oktoberfest

Kingsland Point Park 299 Palmer Avenue, Sleepy Hollow, NY

Feast 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

Sleepy Hollow Street Fair

Beekman Avenue, Sleepy Hollow Beekman Avenue, Sleepy Hollow, NY

The Sleepy Hollow Tarrytown Chamber of Commerce’s annual Sleepy Hollow Street Fair takes place this year on Saturday, October 8th, transforming Beekman Avenue into an outdoor market. October is the most exciting time to visit Sleepy Hollow. The weeks leading up to Halloween have something for everyone: haunted hayrides, Gothic mansions, blazing pumpkins, farmers markets, live music, 5K …

Free
Recurring

Sleepy Hollow Block Party

Beekman Avenue, Sleepy Hollow Beekman Avenue, Sleepy Hollow, NY

Live music, food trucks, entertainment for the whole family! Dance the night away at the annual Sleepy Hollow Block Party before or after the Sleepy Hollow Haunted Hayride! Beekman Avenue from Washington Street to Broadway is closed to traffic both nights of the hayride. There's lots to do before your wagon departs!

Free
Recurring

Sleepy Hollow Haunted Hayride

Sleepy Hollow Village Hall 28 Beekman Avenue, Sleepy Hollow, NY

Climb aboard 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 of downtown Sleepy Hollow. Rumbling off into the dark you realize too late you are heading down the Albany Post Road past the Old Dutch Church, following exactly Ichabod Crane’s flight from …

Recurring

Sleepy Hollow Block Party

Beekman Avenue, Sleepy Hollow Beekman Avenue, Sleepy Hollow, NY

Live music, food trucks, entertainment for the whole family! Dance the night away at the annual Sleepy Hollow Block Party before or after the Sleepy Hollow Haunted Hayride! Beekman Avenue from Washington Street to Broadway is closed to traffic both nights of the hayride. There's lots to do before your wagon departs!

Free
Recurring

Sleepy Hollow Haunted Hayride

Sleepy Hollow Village Hall 28 Beekman Avenue, Sleepy Hollow, NY

Climb aboard 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 of downtown Sleepy Hollow. Rumbling off into the dark you realize too late you are heading down the Albany Post Road past the Old Dutch Church, following exactly Ichabod Crane’s flight from …

There’s something for everyone in the real Sleepy Hollow—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 5K run, Halloween parade, and of course, the Headless Horseman! For the latest on Fall events, visit our guide to Halloween in Sleepy Hollow.