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Event Series Event Series: Winter Stroll

Tarrytown and Sleepy Hollow Winter Stroll

December 3, 2022 @ 5:00 pm - 9:00 pm

Horse and rider dressed as Sinterklaas on Main Street in Tarrytown

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

2022 date: December 3. 5 pm tp 9 pm.

Where: Main Street, Tarrytown, NY 10591

For info: https://www.sleepyhollowtarrytownchamber.com

Ugly sweater contest

It’s that time of year again, when cute fall sweaters give way to your ugliest holiday creations…

Bring your worst ideas to the Trilogy Consignment and Into Leaf Ugly Sweater Open House where you can embellish and decorate to your heart’s content. Adults and kids of all ages are welcome to drop in and enhance their sweaters using the provided notions and expert advice from the staff. BYO sweater or purchase one in the store.

And be sure to stop by Bucci Real Estate Team office the night of the stroll to enter your sweater in the #uglysweater10591 contest they’re sponsoring at the town-wide Winter Stroll on Sat. Dec. 3. There are prizes for best adult, kid, and pet costumes and they’re good! Details for contest posted on @sleepyhollowtarrytownchamber

Details on workshop: Wednesday, Nov. 16 from 4-7 PM at Trilogy Consignment, 54 Main St. in Tarrytown

Cost: $10 per person includes all supplies and light refreshments

What to Bring: A sweater and your best ideas


December 3, 2022
5:00 pm - 9:00 pm
Event Categories:
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Sleepy Hollow Tarrytown Chamber of Commerce
View Organizer Website


Main Street, Tarrytown
Main Street
Tarrytown, NY 10591 United States
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View Venue Website

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.