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Tarrytown, Sleepy Hollow Winter Stroll to Offer Entertainment and Shopping

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November 26, 2022

By Robert Kimmel–       

Within Tarrytown and Sleepy Hollow, on Saturday, December 3, folks will have a variety of festivities to gain their attention and pleasurable participation. The key event is the second annual Winter Stroll during which amblers can enjoy activities ranging from singing groups, theatrical entertainment, warm dining treats, special extended shopping hours, a contest and more.

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The Stroll, courtesy of the Sleepy Hollow Tarrytown Chamber of Commerce, begins at 5:00 p.m. and concludes at 9:00 p.m. and will encompass the villages’ shopping streets including North Broadway, Main Street and Beekman Avenue.

While the Winter Stroll alludes to walking along these streets, the Chamber is offering another means of transportation this year.  “We are providing two Holly Jolly Trolleys decorated with lights and music,” said Stephanie Rodnick, Chamber of Commerce Executive Director. The complimentary trolley rides continuing throughout the evening will make nine stops for passengers as they loop from Patriots Park, along Broadway, down Main Street and back toward Beekman Avenue.  The trolleys are being sponsored by Kendal On Hudson, Rey Insurance, Emerson NY, Allan Block Insurance, J.P. Doyle’s, TaSH and Tomkins Financial.

Some merchants are expected to offer holiday treats, as they did last year, both within their shops and on tables fronting their stores.

Many store windows are also expected to be dazzlingly ornamented as entries in a Storefront Holiday Decoration Contest. An additional competition encourages strollers to take selfies in front of these windows and post them on the Chambers’ Facebook page under hashtag #10591. Visitors to the site can then like, love or comment on the photos. The one with the most comments posted by December 9th at 9:00 wins.

Strollers will be serenaded by at least three groups. The Sleepy Hollow High School Choir, dressed as elves, will sing a cappella Christmas carols. Christ Church’s choir will add to the carols and holiday melodies. Hackley School’s Performing Arts Faculty vocal group will also sing holiday songs. Hackley’s Middle School Drama Group will provide a winter holiday performance, and the Peter Royston Theater will engage an audience in an interactive performance of the adventures of The Pirate King of Christmas.

A somewhat offbeat event, the second annual Ugly Sweater contest, also hosted by the Chamber, returns after making its debut during last year’s Stroll. Participants vie for having the weirdest, ridiculous-looking, unattractive sweater.  The sponsor of that event is the Bucci Real Estate Team, whose office at 4 North Broadway in Tarrytown will serve as the official location to enter a sweater in the contest during the night of the Stroll. Prizes will go to those selected in three categories, best adult, kid and pet costumes.

Earlier strollers will be able to shop for edibles at the 7th Annual TaSH Holiday Market in Patriot’s Park, off North Broadway, beginning at 2:00 p.m. and lasting until 5:30 p.m.  TaSH recently was named as the sixth best market in New York State by voters, and the Holiday Market may draw as many as 50 vendors.

Beginning at 4:30 p.m. in Patriot’s Park, musical selections will precede the Annual Tarrytown Tree Holiday Lighting, scheduled for 5:00 p.m.  “We are anticipating hundreds of people to join the Stroll at the conclusion of the Tarrytown Village holiday festivities that afternoon at Patriots Park,” Rodnick said.

The Historical Society is also inviting the public to visit its One Grove Street headquarters for a Holiday Open House from 5:00 p.m. to 8:00 p.m., featuring live harp music, hot cider, cookies and a holiday exhibit.

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Andrea Martone - Tarrytown, Sleepy Hollow real estate agent

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