Sleepy Hollow Mermaid Festival

Kingsland Point Park 299 Palmer Avenue, Sleepy Hollow, NY, United States

Participate 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 Series Jazz at Horan’s Landing

Jazz at Horan’s Landing

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

Enjoy 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 Series Jazz at Horan’s Landing

Jazz at Horan’s Landing

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

Enjoy 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 Series Jazz at Horan’s Landing

Jazz at Horan’s Landing

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

Enjoy 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 Series Jazz at Horan’s Landing

Jazz at Horan’s Landing

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

Enjoy 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 Park 299 Palmer Avenue, Sleepy Hollow, NY, United States

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 to enter, parking is $5 per car.

Free

Sleepy Hollow Street Fair

Beekman Avenue, Sleepy Hollow Beekman Avenue, Sleepy Hollow, NY, United States

The Sleepy 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 to Halloween have something for everyone: haunted hayrides, …

Free

SUP Witches of Sleepy Hollow Festival

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

Searching 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

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.