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Tarrytown and Sleepy Hollow Winter Stroll
December 13, 2025 @ 2:00 pm - 6:00 pm
Free
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.
The 5th annual Tarrytown and Sleepy Hollow Winter Stroll takes place Saturday, December 13th! Extended shopping hours, outdoor dining, story telling, Holly Jolly Trolleys, holiday treats, carolers, ugly sweater contest, live entertainment and other special events!
2025 date: December 13. 2 pm to 6 pm.
Where: throughout the downtowns of Tarrytown and Sleepy Hollow!
Related Events
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.