Must-See Live Music in Portland This Week!
As fall settles into Portland, the live music scene is still going strong! This Saturday, September 21st, you’ve got a couple of great options. Kick off the afternoon at Austin Street Brewery’s 2nd annual Oktoberfest celebration, featuring live music from local favorites Hambone, along with special draft beers and fun games. Later that evening, head to One Longfellow Square to catch Boston’s Divine Sweater, fresh off their 2023 tour where they sold out shows at renowned venues across the country.
Looking for more live music? Check out Live Music Tonight, our full calendar of live music in Portland.
THE HEADLINER

Chicago-born singer-songwriter David Kushner, now based in Los Angeles, gained widespread recognition in 2022 with the release of “Miserable Man” and “Mr. Forgettable” from his debut EP, Footprints I Found. These breakout tracks racked up over a billion streams in less than a year. His 2023 single “Daylight” swiftly went platinum, propelling Kushner to further success. That same year, he made an appearance on The Tonight Show Starring Jimmy Fallon and completed two headline tours. With an impressive 13.7 billion TikTok views and a million new Instagram followers in under six months, Kushner’s rise has been nothing short of meteoric.
Tuesday, September 24th at State Theatre
LIVE & LOCAL

Austin Street Brewery is gearing up for their second annual Oktoberfest celebration, and it’s shaping up to be a must-attend event! Enjoy a curated special draft lineup, exclusive beer release, and limited-edition glassware to mark the occasion. Local favorites Hambone will take the stage, delivering their signature blend of modern soul tunes to keep the vibes high. The party doesn’t stop there—expect an array of food trucks, games like bocce ball, and a classic stein-holding competition for some friendly fun.
Saturday, September 21st at Austin Street Brewery
MIDWEEK MUSIC

Doom Flamingo is a dynamic synth-rock group from Charleston, South Carolina, blending the vibrant energy of Top Gun-style guitar riffs and Miami Beach lounge vibes with dark, eerie synth soundscapes reminiscent of John Carpenter films. Known for their “Jekyll and Hyde” approach to songwriting, they effortlessly shift between upbeat, feel-good tunes and haunting, cinematic atmospheres. Born from organic friendships and past collaborations, the band features powerful vocals and an electrifying ensemble of musicians, delivering a unique and captivating live experience.
Wednesday, September 18th at Portland House of Music
STAFF PICK

Boston-based Divine Sweater delivers a dreamy, groove-driven sound defined by tight vocal harmonies and dynamic energy. They independently released two albums in 2019 and 2021, which have amassed over ten million streams, before dropping their third album, Down Deep, in 2023 through Better Company Records. With songs featured on major Spotify and Apple Music playlists like “Chill Vibes,” “Undercurrents,” and “Radar US,” the band maintains over 100k monthly listeners on Spotify, 60k TikTok followers, and 12k on Instagram. Recently named Indie Artist of the Year by the Boston Music Awards, Divine Sweater’s 2023 headline tour saw sold-out shows at iconic venues such across the United States.
Saturday, September 21st at One Longfellow Square
This is just a sample of what’s happening this week. Check out the Live Music Tonight page for a full calendar of live events happening in Portland, Maine.