J. P. Doyle’s Annual VIP Block Party

J. P. Doyle's 48 Beekman Avenue, Sleepy Hollow, NY

J. P. Doyle's Annual Block Party marks the unofficial start to Sleepy Hollow's Halloween season. VIP tickets include priority seating for 4 live band performances, premium bar, J. P. Doyle's …

$150

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, …

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 …

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 …

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 …

Free

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.