These Ugly Sweater Parties Deliver Holiday Fun in the Hudson Valley

Bust out your most hideous holiday-themed sweater for these events, bar crawls, and parties in the Hudson Valley.

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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.

Adobe Stock / Photo by New Africa

In a bind for a sweater? Here are some perfect picks to get you prepped for all your parties:

Reindeer ugly sweaterLight-Up “Oh Deer!” Sweater

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Naughty or Nice Sweater

Drink-Holding Christmas Tree Sweater

Ugly Christmas Sweater Paint & Sip

Van Schaick Island Country Club, Cohoes
December 8, 6-8 p.m.

Get festive in your ugly sweaters this weekend as you paint a personalized portrait of Kris Kringle. Head to Durrant’s at Van Schaick for this holiday event during which you will be given a wooden pallet and art supplies to create your own Santa-inspired piece to take home. Admission include one complimentary drink to put you in the holiday spirit.

Holiday Trivia

Allan’s Falafel, Chester
December 14, 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 holiday lore and traditions from around the world to prep for this themed 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.

Holiday Celebration

Wiltwyck Rural Cemetery, Kingston
December 16, 12-2 p.m.

Gather with the Kingston community in your ugly sweaters at the Wiltwyck Cemetery to celebrate all December holidays. Entertainment includes the Key of Q a capella chorus singing secular holiday songs along with light refreshments throughout the performance. For a donation of $10, you can take home an ornament, the sale of which goes towards a tree-planting fund to keep the cemetery lush and beautiful for decades to come.

Cocoa Around the World

Muscoot Farm, Katonah
December 16, 2 p.m.

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This sweet event features hot chocolates from around the world, all in one place. Dress up in your ugly sweaters to really get into the festive spirit and sample cocoas from across the globe and assemble your own hot chocolate mix to take home. In addition to last year’s offerings, the 2023 event will feature even more options to try.

White Plains Ugly Sweater Bar Crawl

White Plains
December 16

Join fellow Westchester natives as they turn White Plains into the North Pole this December. Taking place in honor of National Ugly Sweater Day, this bar crawl has a jam-packed day, complete with a costume contest to crown a festive winner or group. Throughout the day, enjoy food and drink specials and DJs at the city’s best bars and follow the digital crawl map to meet up with fellow partiers.

Annual Ugly Sweater Party

Brown’s Brewing Company, Troy
December 22, 9 p.m.

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.

Ugly Sweater Contest

Babblers at Wylder Windham, Windham
December 23, 5-7 p.m.

Wylder Windham invites resort guests and Windham locals to Babblers on December 23 for a fierce ugly sweater competition. Enjoy delicious eats and cocktails at the kill-side hotspot while you connect with others in holiday attire. Whoever comes in the best sweater wins a $50 gift card to Babblers, so make sure to dress for the occasion.

Related: Where to See Santa in the Hudson Valley This Holiday Season

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