Tarrytown and Sleepy Hollow Winter Stroll

Main Street, Tarrytown Main Street, Tarrytown, NY

Kick off the Holiday season on December 3rd with the second annual Tarrytown and Sleepy Hollow Winter Stroll!  Extended shopping hours, outdoor dining, holiday treats, carolers, ugly sweater contest, live entertainment and other special events hosted by the Historical Society and local retailers!


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.