Tarrytown & Sleepy Hollow Winter Stroll

Sat Dec 13, 2025
2:00pm to 6:00pm ET
Age: all ages
Price: FREE
Location:
Downtown Tarrytown
Main St, Tarrytown, NY, 10591
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Experience the charm of the season as the towns of Sleepy Hollow and Tarrytown come alive with festive lights, warm treats, and joyful celebrations. Enjoy extended shopping hours, outdoor dining, storytelling, a holly jolly trolley, holiday treats, carolers, an ugly sweater contest, live entertainment, and other special events!

FREE Transportation:  Take a stroll or hop-on-and-off a FREE jolly trolley or luxurious Party Bus to visit participating businesses in both villages.

See the website for details on how to enter the ugly sweater contest.

 

** Activity dates/times are subject to change. Please click through to the activity website to verify.