Tarrytown, Sleepy Hollow Winter Stroll to Offer Entertainment and Shopping

November 26, 2022

Robert Kimmel –

There will be a variety of festivities in Tarrytown and Sleepy Hollow on Saturday, December 3rd to capture their attention and enjoy their participation. The main event is the second annual Winter Walk, during which walkers can enjoy a variety of activities including singing groups, theatrical entertainment, heartwarming food, special extended shopping hours, competitions and more.

The Stroll, presented by the Sleepy Hollow Tarrytown Chamber of Commerce, runs from 5:00 pm to 9:00 pm and will include the Village’s shopping streets of North Broadway, Main Street and Beekman Avenue.


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While a winter walk implies walking along these streets, the Chamber of Commerce is offering another form of transportation this year. “We provided two Holly Jolly carts decorated with lights and music,” said Stephanie Rodnick, executive director of the chamber. The free streetcar will run throughout the night, with riders making a detour from Patriot Park, down Broadway, down Main Street, and back to Beekman Avenue, making nine stops. These carts are sponsored by Kendal On Hudson, Rey Insurance, Emerson NY and Allan Block Insurance.

During stroll hours, regular traffic will be restricted on major streets from Broadway to Washington Street, allowing restaurants to extend their tables from the sidewalk to the street. Some businesses are expected to offer holiday gifts in-store and on storefront tables, as they did last year.

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Many store windows will also be gaudyly decorated as entries in the Storefront Holiday Decoration Contest. An additional contest encouraged strollers to take selfies in front of these windows and post them on Chambers’ Facebook page with the hashtag #10591. Visitors to the site can then like, like or comment on those photos. The person with the most comments by December 9th at 9:00 wins.

Strollers will be serenaded by at least three sets. The Sleepy Hollow High School Choir, dressed as elves, will sing a cappella Christmas carols. The Christ Church choir will join in the carols and festive melodies. Holiday songs will also be sung by the Hackley School’s Academy of Performing Arts vocal group.Hackley’s middle school drama troupe will offer winter break performances, while the Peter Royston Theater will engage audiences in an interactive performance about the adventures of Hackley One Piece for Christmas.

The second annual Ugly Sweater Contest, also hosted by Chamber, is a somewhat offbeat event that’s back after debuting at last year’s Stroll Conference. Participants compete for the weirdest, most ridiculous, and least appealing sweater. The event is sponsored by the Bucci Real Estate team and their offices at 4 North Broadway in Tarrytown will serve as the official venue for competition at Stroll Night. Prizes will be awarded to the best adult, kids and pet apparel in three categories.

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Earlier strollers will be able today The annual TaSH Holiday Market at Patriot Park near North Broadway runs from 2:00 p.m. to 5:30 p.m. TaSH was recently voted the sixth best market in New York State by voters, and the holiday market can attract as many as 50 supplier.

Beginning at 4:30pm in Patriot Park, music selections will be performed ahead of the annual Tarrytown Christmas Tree Holiday Light Show scheduled for 5:00pm. Patriot Park,” Rodnick said.

The Historical Society also invites the public to its Holiday Open House at its One Grove Street headquarters from 5:00pm to 8:00pm, which includes live harp music, mulled cider, cookies and holiday displays.

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