Portland ME Ugly Sweater Bar Crawl 2026

Portland Maine’s Ugly Sweater Pub Crawl brings America’s most beloved small city’s bar culture and New England holiday spirit to the holiday sweater tradition in the best finale possible for a 244-city national event. The Old Port and the Arts District bar districts are consistently ranked among the best bar scenes in America and on ugly sweater night the combination of Portland’s extraordinary culinary and craft beer culture, the lobster fishing heritage, and the excellent local bars creates a holiday celebration that Portland Maine does better than almost any city its size in America.

Our Portland Maine route moves through the Old Port and the surrounding bar district, stopping at venues that represent the full quality of what Portland’s extraordinary bar and culinary scene has built. The ugly sweater competition in Portland draws on the creative energy of an arts, culinary, and outdoor adventure community and the entries reflect that Maine combination of culinary excellence, New England independence, and genuine Portland creativity that has made this city one of the most celebrated pub crawl destinations in the country.

December in Portland Maine is very cold, typically ranging from 15 to 28 degrees at night, with the possibility of snow. The Maine winter is serious and the Old Port at Christmas with the historic brick buildings and the harbor backdrop creates one of the most beautiful and authentic holiday pub crawl settings in New England. Portland Maine ugly sweater night is the perfect way to close out a national event series.

Our hosts manage the Portland Maine route with local knowledge. Specials are confirmed, wristbands handle entry at every stop, and the ugly sweater contest brings Old Port creativity to the holiday season.