The first sweater you notice at an ugly sweater bar crawl is always the one with a battery pack. By hour three it's the only light source in the corner booth, and its owner is the most popular person in the bar. That glow is the whole point of an ugly sweater bar crawl, and in 2026 it's coming to eight cities over two Saturdays.
Best Ugly Sweater Bar Crawls by City in 2026
Every crawl runs a single afternoon into the evening, so you can hit multiple bars without losing the whole weekend. Here is the full lineup.
Saturday, December 12 (2pm to 9pm)
Boston: 500+ expected. Past stops include Tiki Rock, Wild Rover, Hong Kong Bar and Sissy K's.
Chicago West Loop: 500+ expected. Think PB&J Bar, Grapes and Grains, Esco Bar and Bandit.
Detroit: 500+ expected, with rooftops like Level Two and Exodos plus the Bar Humbug Xmas Pop-up.
Saturday, December 19
Hoboken, 1pm to 8pm: 1,000+ expected, with bars like Birch, Wild Moose Saloon and River Street Garage.
Charlotte, Cleveland and Raleigh, 2pm to 9pm: Charlotte (500+), Cleveland (1,000+) and Raleigh (1,000+).
Philadelphia, 3pm to 10pm: 1,000+ expected, with Lucy's, Woody's, Concourse and Bar X on the radar.
Bar lineups can change, so check the event page for the current bar list before you plan your route.
Which Ugly Christmas Sweater Bar Crawl Should You Pick?
Hot take: pick the crawl you can reach without a flight and a hotel, because the best part is the dumb, spontaneous stuff. A stranger will want to trade hats. Someone will sing. You'll make a friend named Kyle.
If you like a cozier crowd, the December 12 cities are expected to draw 500+ each, which is plenty of sweaters without feeling like a stadium. If you want the biggest possible party, December 19 is where Cleveland, Raleigh, Hoboken and Philadelphia each expect 1,000+. Cleveland even has a Santa's Dive Xmas Pop Up Bar on its route, which is exactly as chaotic as it sounds.
Not sure? Text the group chat the two nearest cities and let the loudest friend decide. Democracy is overrated when there are antlers involved.
The Ugly Sweater Tier List
We've seen a lot of knitwear. Here is how it ranks.
S tier: light-up sweaters with a battery pack you can actually reach. You will want to turn it off when you sit down.
A tier: matching group sweaters. Three reindeer in a row photograph better than any solo outfit.
B tier: the thrifted grandpa cardigan. Respectable, but you will not be remembered.
C tier: a regular sweater with one sticker on it. We see you. We do not count you.
What to Know Before You Go
Layers beat bulk
Bars get hot and the walk between them does not. Wear a thin tee under the sweater so you can peel off the knit when the room gets steamy, and bring a coat you don't mind carrying.
Protect the electronics
Pack spare batteries for any LED sweater.
Charge your phone to full. Cold weather drains it fast.
Wear shoes you can walk in, since you'll be on your feet from the first bar to the last.
Book your ride home early. Everyone leaves at the same time.
Arrive early
Check-in goes faster at the start, and the first hour is when the bars still have elbow room. Start strong and the afternoon takes care of itself.
Pace yourself
The rookie mistake is treating the first bar like the finale. You have roughly seven hours, and nobody has ever said "I wish I'd gone harder in the first forty minutes." Alternate every drink with water, eat something real before you start, and save your loudest Mariah Carey impression for the last stop.
Also, take the group photo early. By hour five the sweaters are crooked, the antlers are gone and nobody remembers whose coat is whose. Get the clean shot while everyone still looks like they planned this.
Ready to Crawl?
Pick your city, grab your crew and commit to the most ridiculous sweater you can find. Browse every date, time and ticket option on our bar crawl page and lock in your spot before the best ugly Christmas sweater bar crawl of the year fills up.