NY’s Favorite Halloween Town Is Hosting A Festive Christmas Stroll This December
The Headless Horseman will have to abandon his spooky demeanor ahead of the Tarrytown & Sleepy Hollow Winter Stroll on Saturday, December 14th — the fourth annual celebration of its kind. Both the iconic Halloween figure and autumnal hotspot are switching gears and welcoming winter with an evening of holiday events, from caroling to competing in an ugly Christmas sweater contest.
For New Yorkers looking for a day trip out of the city, this is the perfect escape: hop aboard the MetroNorth and then onto the towns’ free trolley rides that will shuttle visitors to and from the different happenings throughout the afternoon: Christmas lights and decor, live music, ornament making for kids, and more. If you’re feeling extra jolly, you can also participate in the ugly center contest — and for locals in town, the holiday storefront decoration contest. Prizes will be awarded to winners in the form of gift cards to mom and pop establishments.
And of course, while you’re on your journey, be sure to have a look inside all of the stores welcoming shoppers who are looking to pile presents under the tree. Pretty Funny Vintage and the Sleepy Hollow Bookshop are just a few of the stores you’ll encounter along the crawl. And if you’re looking to grab a bite while out and about throughout the towns, local favorites like the Set Back Inn will serve special holiday cocktails while DeCicco’s will pass out hot chocolate. Other eateries participating in the festive occasion include Beekman Ale, Casaletto Pizza, Horsefeathers, and La Taqueria La Perla Poblanita, to name just a few.
While, yes, the spooky sanctuary in the Hudson Valley might’ve gotten its name for its epic fall festival, beloved Great Jack O’Lantern Blaze, and eerie history, we can’t imagine forgoing the area’s newfound Christmastime tradition, either. Why not make Sleepy Hollow and Tarrytown must-visits on your fall and winter bucket lists? Abraham Van Brunt is nodding his head in agreement. (We kid!)
Check out the Tarrytown Sleepy Hollow Chamber of Commerce for more information about the Christmas Stroll’s complete schedule, trolley stops, and more.
Saturday, December 14th
From 3–7pm
Throughout downtown Sleepy Hollow and Tarrytown
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