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As the temperature drops, spirits go up thanks to festive events and celebrations around the Hudson Valley. Forget about fashion faux pas this December and don your favorite ugly sweater to one of these parties to celebrate the holiday season. Whip out the glue gun to create your own ugly abomination or shop for a novelty knit featuring a witty joke or seasonal character.
In a bind for a sweater? Here are some perfect picks to get you prepped for all your parties:
Naughty or Nice Sweater | Drink-Holding Christmas Tree Sweater | Light-Up “Oh Deer!” Sweater
Ugly Sweater Run
Fleet Feet, Poughkeepsie
December 8, 9 a.m.
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Get your sweat on in your ugly sweater at Fleet Feet Poughkeepsie’s annual Ugly Sweater Run. The fun run is an untimed 5k, so the event is open to runners of all paces, levels, and abilities. All participants will receive a custom pair of ugly sweater socks, and ugly sweater-themed bib, and a custom handmade finisher’s medal. After the run, indulge in apple cider and donuts, and stick around for the awards ceremony for best costumes.
Holiday Trivia
Allan’s Falafel, Chester
December 12, 6-8 p.m.
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Show up to this seasonal trivia night at Allan’s Falafel in your ugly sweater for the chance to win extra prizes. Read up on your fun facts to prep for this general knowledge trivia session. Reservations are required, and there is no limit on team members, so invite your whole festive gang. If you come early, you can take advantage of happy hour starting at 4 p.m. for great deals on beer, wine, and sangria.
Ugly Sweater Holiday Pop-up Networking Event
Saxon Hall, Newburgh
December 12, 6-9 p.m.
Looking to meet new people while wearing the ugliest sweater you own? Use your attire as a great conversation starter at Saxon Hall’s holiday networking event this December. Connect with fellow professionals, enjoy festive drinks, and possibly win a prize for the ugliest sweater. Kick off the holidays in style at this themed mingling celebration.
Ugly Sweater Party
Vosburgh Brewing, Elizaville
December 14, 1-8 p.m.
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Grab a brew at Vosburgh in your hideous holiday sweater during this all-day party in Columbia County. As you sip your craft beers, enjoy delicious bites and live music courtesy of Payne’s Grey Sky. All proceeds collected by the band will be donated to Christmas Wishes Ulster County, Inc to provide local kids with an unforgettable Christmas.
White Plains Ugly Sweater Bar Crawl
White Plains
December 21, 4-10 p.m.Â
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Join fellow Westchester natives as they turn White Plains into the North Pole this December. For bar crawl veterans and newbies alike, this festive event is a jam-packed day complete with festive drinks, live music, and access to over four of the city’s bars. Throughout the day, enjoy food and drink specials and DJ sets and follow the digital crawl map to meet up with fellow partiers.
Ugly Dog Sweater Contest
Wylder Windham, Windham
December 21, 6-7 p.m.
Wylder Windham invites resort guests and Windham locals on December 21 for a fierce ugly dog sweater competition. Bring your pups along and dress them up in the ugliest dog sweaters you can find to take some memorable photos. The winner will receive a $50 gift card to the onsite Babblers restaurant.
Ugly Sweater Party
Angry Orchard Cider House, Walden
December 21, 6-9 p.m.
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Forget the beer and party with hard ciders instead at Angry Orchard’s Cider House in Walden for this sweater party. The Orange County destination invites locals to come and get their holiday groove on in their “loudest, tackiest, most heinous holiday outfits.” Sip sweet ciders and dance to the tune of live band karaoke with Hillbilly Parade. The winner of the ugly sweater contest will win a special Angry Orchard gift.
Fugly Sweater Party
Brown’s Brewing Taproom, Troy
December 21, 8-11 p.m.
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Wear your worst-best holiday sweater to Brown’s Brewing Company this December for the chance to win a special prize. Enjoy beer, food, and live music from Road Soda Pop with your friends as you dance the night away in your tacky ensemble or seriously silly sweater or vest.
Related: Where to See Santa in the Hudson Valley This Holiday Season
