Rockwood Ramble 10k

Rockwood Hall 1 Rockwood Road, Sleepy Hollow

Starting and finishing in historic Rockwood Hall, the annual Rockwood Ramble 10K is a favorite. Scenic Hudson River views greet runners before the course veers into the woods. The wide …

$30 – $50

Tarrytown Street Fair

Main Street, Tarrytown Main Street, Tarrytown

The Sleepy Hollow Tarrytown Chamber of Commerce’s annual Tarrytown Street Fair takes place this year on Sunday, June 4th. Main Street transforms into an outdoor market with food, music, local retailers, arts …

Free
Event Series Kykuit Tours

Kykuit Tours

Philipsburg Manor 381 North Broadway, Sleepy Hollow

A majestic paradise with sweeping river views. See the Hudson Valley’s top cultural attraction! Built between 1906 and 1913, Kykuit was home to four generations of the Rockefeller family, beginning …

$25 – $75

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.