Portland, Maine is sparkling with cozy, quirky, and downright festive things to do this week, so let’s dive right into your game plan.

If you’re in town on Christmas Day itself, much of the city is in quiet mode, but that just makes it perfect for a peaceful wander through the Old Port, a brisk walk on the Eastern Prom, or a cocoa-fueled stroll to check out the Monument Square holiday tree. The City of Portland notes that city services pause for the holiday, which means the streets feel extra calm and magical. It’s a great day for listeners to lean into the slower side of Portland: grab a coffee from a spot that’s open, bundle up, and enjoy the harbor views without the usual bustle.

As the week rolls into Friday, the energy picks up. Portland Old Port’s weekend guide for December 26th through 28th highlights a mix of concerts, comedy, and family-friendly happenings across town. They point listeners toward local shows at venues like the State Theatre and Portland House of Music, plus festive gatherings in neighborhood bars and breweries where you can catch live music with a holiday twist, sip something warming, and meet locals who’ll happily tell you their favorite hidden corners of the city.

If you’re a live-music lover, Portland Maine Theater’s December listings show tribute acts and seasonal performances continuing through the week, including touring bands and holiday-themed shows at downtown venues. This is the time to check who’s on stage at the State Theatre or Merrill Auditorium and snag same-week tickets for a spontaneous night out.

Film fans should keep an eye on the Portland Museum of Art’s film program, PMA Films. According to the museum’s events calendar, they’re screening international and indie titles through the holiday week, with afternoon and evening showtimes that pair perfectly with a slow museum visit and a winter walk through the Arts District afterward.

For listeners looking for community-focused events, the Equality Community Center on Casco Street hosts LGBTQ+ meetups, support groups, and social gatherings throughout December. Their queer events calendar shows an ongoing rhythm of meetings, movie watch parties, and game nights during the month, making it a welcoming hub if you want to plug into local community while you’re in town.

Wrap up your weekend by combining a harborfront walk, a great local meal, and a show or film, and you’ve got the perfect Portland winter story to take home.

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