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Westchester County
Whiskey Lounge – White Plains
152 Mamaroneck Ave, White Plains, NY 10601
Join the ultimate Ugly Sweater Christmas Party with prizes for the ugliest sweater and a coquito contest. Party runs 7 pm–2 am.
Event info & tickets
Winter Stroll & Sweater Contest – Tarrytown & Sleepy Hollow
4 North Broadway, Tarrytown, NY
Snap a photo in your ugly sweater at the Bucci Real Estate Team tent during the Winter Stroll (Dec 13, 2–6 pm) and enter to win prizes.
Half Moon – Dobbs Ferry
341 Main St, Dobbs Ferry, NY
Cocktail party on Dec 22 from 6–8 pm with complimentary drink, light bites, and prizes for the top three ugliest sweaters. Admission: $50.
Hudson Valley Highlights
Hudson’s Mill – Garnerville
10 Rockland Lake Rd, West Haverstraw, NY 10993
Brunch party (Dec 14, 12–4 pm) with live music, holiday sing-alongs, and prizes for the ugliest sweater. Tickets: $30.
Brown’s Brewing Taproom – Troy
107 Congress St, Troy, NY 12180
Fangly Sweater Party on Dec 19 at 9 pm with craft beer and live music.
Valatie Bar & Grill – Valatie
2170 US-9, Valatie, NY 12184
Dec 19 at 9 pm: DJ, drink specials, photo ops, and prizes for ugliest, funniest, or most creative sweaters.
Robibero Winery – New Paltz
714 Albany Post Rd, New Paltz, NY 12561
Dec 20, 11 am–6 pm: Ugly Sweater “Sip & Steal” with wine, cocktails, s’mores, pizza, and a 3 pm sweater contest.
Angry Orchard Cider House – Walden
1 Ironworks Hill Rd, Walden, NY 12586
Dec 20, 6–9 pm: Karaoke with Hillbilly Parade, cider tastings, and sweater contest.
PLAY – Poughkeepsie
188 Main St, Poughkeepsie, NY 12601
Dec 27 at 8 pm: Indoor party with Happy Hour, holiday movie, food, and music by TOMMMYDIDIT. Entry: $15.
Quick Look by Date
- Dec 13 – Tarrytown/Sleepy Hollow Winter Stroll & Sweater Contest
- Dec 14 – Hudson’s Mill Ugly Sweater Brunch (Garnerville)
- Dec 18 – Whiskey Lounge Ugly Sweater Party (White Plains)
- Dec 19 – Brown’s Brewing (Troy) & Valatie Bar & Grill (Valatie)
- Dec 20 – Robibero Winery (New Paltz) & Angry Orchard (Walden)
- Dec 22 – Half Moon Cocktail Party (Dobbs Ferry)
- Dec 27 – PLAY Ugly Sweater Party (Poughkeepsie)
So dig out that hideous holiday sweater, add some glitter if you dare, and join the fun! These parties are all about laughter, festive vibes, and making memories that are just as colorful as your outfit. Ugly never looked so good—see you on the dance floor!
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