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LifestyleHolidaysWinter Holidays

SantaCons and ugly sweater parties on Long Island

Guests sit by the fire in their ugly

Guests sit by the fire in their ugly holiday attire during the annual Ugly Sweater Party held at the Post Office Cafe in Babylon. Credit: Nicole Starr Castillo

The winter holiday season has become an awesome excuse to wear dreadful duds or to cosplay like Saint Nick — and if you really need to show off your holiday fashion misfires, or can’t wait to walk the streets in Santa style, here’s where to wear your woolen worst. 

East Brentwood Fire Department's SantaCon 

An ugly sweater party and SantaCon combo, this event is also a department fundraiser. Guests can take part in a 50/50 raffle. Tickets are $30 in advance; call 631-463-7680 or 631-922-7077 for purchase.

WHEN | WHERE 8 p.m. Friday, Dec. 13; 26 Fulton St., East Brentwood; 631-273-4560,

Whiskey Down Diner's Ugly Sweater Party 

Holding its first ugly sweater party ever, this fairly new spot (opened in June) suggests guests try wearing their ugliest holiday attire possible to win a prize. A holiday cocktail menu (including boozy hot chocolate) and drink specials will be available. No cover.

WHEN | WHERE 8 p.m. Friday, Dec. 13; 252 Main St., Farmingdale; 516-927-8264,

Great South Bay Brewery's Ugly Sweater Beer + Yoga with Puppies

This party combines three of your favorite things: beer, puppies and yoga. Throw in a holiday sweater (and bring your own mat) and you'll be set to find your zen while adoptable dogs roam around the room. The event is hosted by Beer Fit Club and Smithtown's One Love Dog Rescue, Inc. Tickets are $30, or pay $35 and score a signature Beer Fit Club pint glass. A portion of the proceeds will be donated to the rescue group. Tickets available online at

WHEN | WHERE 10:45 a.m. Saturday, Dec. 14; 25 Drexel Drive, Bay Shore; 631-445-4648,

SantaCon Farmingdale

Participants are asked to dress in holiday flair — as Saint Nick, a menorah, a reindeer or a dreidel, to name a few. The holiday party takes place on Main Street, where food and drink specials will be offered at participating venues (The Nutty Irishman, Croxley's Ale House, Dark Horse Tavern, Library Cafe, That Meetball Place, Alibi Speakeasy, Vintage Wine Bar, Blue Hawaiian, Daytona’s; the after-party takes place at Nutty Irishman). Tickets, $25, are available at A portion of proceeds benefits Toys of Hope children’s charity.

WHEN | WHERE noon-4 p.m. Saturday, Dec. 14; Main Street, Farmingdale

The Leaky Lifeboat's Ugly Sweater Party

The always-festive Leaky is going to reward the person with the “Worst Sweater” a $50 gift card. No cover.

WHEN | WHERE 8 p.m. Saturday, Dec. 14; 3603 Merrick Rd., Seaford; 516-804-9870  

Ugly Sweater Christmas Trivia Party

Shandon Court combines its ugly sweater party with trivia night — so expect holiday-themed questions. There will be prizes for top outfits and cash prizes will be awarded for first and second place trivia winners. Teams of up to six players are welcome. Drink specials and a “Winter Drinks” menu will be available as well. $5 to play trivia; no cover to enter.

WHEN | WHERE 7:30 p.m. Wednesday, Dec. 18; 115 E Main St., East Islip; 631-581-5678,

Post Office Cafe's Ugly Sweater Party 

Guests can enjoy drink specials and live music. Prizes will be awarded for the ugliest sweaters. No cover.

WHEN | WHERE 9 p.m. Thursday, Dec. 19; 130 West Main St., Babylon; 631-669-9224,

Rescuing Families Ugly Sweater Bingo Party

A nonprofit that helps homeowners with disabilities or those dealing with financial hardships get home improvements, Rescuing Families, Inc. is hosting a bingo night (with monetary prizes) that will also offer 40 baskets for raffle. Appetizers, desserts and drinks (including beer, wine and sangria) will be available. Prizes will be given for the ugliest, funniest and most original sweaters. $25 gets guests five bingo games; buy online at

WHEN | WHERE 6:30 p.m. Friday, Dec. 20; VFW Post 2718: 68 Lincoln Road, Franklin Square; 516-697-9403,

Maxwell’s Rock Ugly Sweaters Party 

A DJ will spin hits as guests hang out in their unattractive holiday attire. $5 at the door.

WHEN | WHERE 9 p.m. Friday, Dec. 20; 501 Main St., Islip; 631-210-0011,

Mulcahy's Pub & Concert Hall

Equipped with even more space following a recent expansion, its annual ugly sweater party will feature music by Plunge, plus beats by DJ Savage. Drink specials will be offered and the guest with the ugliest sweater wins a TV. Tickets are $5 in advance at; $10 at the door. VIP seating and party packages available; call or email to reserve or for more info.

WHEN | WHERE 10 p.m. Friday, Dec. 20; 3232 Railroad Ave., Wantagh; 516-783-7500,

Po' Boy Brewery's "Beer Roulette"

The brewery is hosting its “beer roulette” — which means guests are asked to bring a gift-wrapped beer and will then receive a mystery wrapped beer in return. A $25 gift certificate will be awarded to the guest in the ugliest sweater. No cover.

WHEN | WHERE 4:30 p.m. Saturday, Dec. 21; 200 Wilson St., Port Jefferson Station; 631-828-1131,

Vauxhall's Holiday Party

The guest who’s deemed to be wearing the "worst" sweater scores a $50 gift card. No cover.

WHEN | WHERE 8 p.m. Saturday, Dec. 21; 26 Clinton Ave., Huntington; 631-425 0222,

Croxley's Ugly Sweater Party

Holding events at all Croxley’s locations, participants can enjoy drink specials while showing off their holiday "worst." $100 cash will be given for the ugliest sweater, while a $75 gift card goes to the second-place winner and $50 gift card for third. No cover.

WHEN | WHERE 10 p.m. Monday, Dec. 23; locations in Farmingdale, Franklin Square, Rockville Centre and Smithtown;

Ugly Sweater Fun Run

The outing will take place along a marked three-mile course, but participants are welcome to run as much — or as little — as preferred, then stick around when store merch and gift cards will be raffled off. There's no charge to run, but all are asked to RSVP in advance; all are also invited to bring a nonperishable food item or monetary donation to benefit the Sayville Food Pantry.

WHEN | WHERE 7:30 p.m. Tuesday, Dec. 24; Sayville Running Company: 49 Main St., Sayville; 631-589-5700,

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