Join us for a magical evening at the Tarrytown and Sleepy Hollow Winter Stroll! Experience the charm of the season as our historic towns come alive with festive lights, warm treats, and joyful celebrations. There will be outdoor dining, story telling, holiday treats, carolers, ugly sweater contest, extended shopping hours, live entertainment and other special events! Our Holly Jolly Winter Trollies will shuttle you around the downtowns of the two villages.
Don’t miss this opportunity to create lasting memories with family and friends. Bundle up, bring your loved ones, and immerse yourself in the winter wonderland of Tarrytown and Sleepy Hollow!
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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.