If you’re in Portland, Maine this week, you’ve picked a fantastic time to lean into the holidays, the lights, and a whole lot of live music and mischief.
Let’s start with today. Over on Congress Square, the Portland Museum of Art is throwing open its doors for December Lights. According to the Portland Museum of Art’s own events calendar, the museum is free all day, with extended hours from 10 in the morning until 8 at night. They’re packing the building with seasonal cheer: family activities, live music tucked between the galleries, and cozy after-hours shopping in the museum store. It’s the perfect warm-up stop between Old Port errands or before a night out.
If you’re looking to turn tonight into a full-blown night on the town, there are some big sounds waiting for you after dark. JamBase lists country group 12/OC hitting the Cross Insurance Arena at 6:30 p.m., bringing a modern country energy right into the heart of downtown. Just a short walk away, State Theatre’s concert calendar on JamBase also shows Pink Talking Fish with Weird Phishes playing a mash‑up of Pink Floyd, Talking Heads, and Phish, ideal for listeners who love a jam band vibe with a twist.
Over on Temple Street, Portland House of Music has its own holiday groove going. Their calendar shows The Red Eye Flight Crew presenting “It’s A Holiday Soul Party,” performing Sharon Jones’ iconic Christmas album in its entirety. Doors open in the evening, so you can stroll in after dinner and sink into horns, organ, and serious soul power, all dressed up for the season.
If you want something a little more theatrical, The Hill Arts is hosting Vivid Motion Dance’s Holly Jolly Follies. The Hill Arts describes it as Portland’s longest‑running burlesque‑style holiday tradition, a brand‑new show each year with dance, humor, and a very grown‑up kind of festive sparkle. It’s the kind of show that pairs well with a cocktail and a sense of adventure.
As the week rolls on, Portland leans into the “naughty and nice” holiday mood. Eventbrite lists Portland, ME SantaCon 2025 based out of Mathew’s on Free Street, with check‑in between 4 and 7 p.m. It’s a 21‑plus bar crawl run by PubCrawls.com, so expect a sea of Santas tumbling through the Old Port, hopping from bar to bar with holiday drink specials and plenty of people‑watching.
Looking toward the rest of the weekend, The Hill Arts schedule hints at more offbeat holiday options: everything from drag shows like Dragology’s Feelin’ Frosty to raucous variety and cabaret nights that mix live music, comedy, and circus‑style performance. It’s a reminder that if you’re craving something weird, witty, and very Portland, there’s always a stage somewhere ready to oblige.
So whether listeners want family‑friendly lights and art, big arena country, jam‑band marathons, sultry holiday burlesque, or a tipsy night out in a Santa suit, Portland has the week fully covered.
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