• Square to Square Outdoor Concert Series: Sunburned Sharks

    Congress Square Park Portland, ME, United States

    Presented in partnership with One Longfellow Square! *also serving as the rain location   Based in Portland, Maine, Sunburned Sharks delivers sun-soaked indie-funk R&B distilled from 60s soul, 70s funk, 80s pop, 90s rock, R&B, and classic rock rolled into one “gritty vintage-meets-polished modern” vision. With bright guitar lines that catch the light like ocean spray, go-down-smooth

  • Square to Square Outdoor Concert Series: Tricky Britches

    Congress Square Park Portland, ME, United States

    Presented in partnership with One Longfellow Square! *also serving as the rain location Tricky Britches is a high-energy string band hailing from Portland, Maine. With their original songs and traditional roots, the band blends bluegrass, country, folk, and rock into a unique, driving sound that always brings people to the dance floor. Formed in 2009, Tricky

  • Square to Square Outdoor Concert Series: Sigrid Sibley + Thomas Charles Clukey

    Congress Square Park Portland, ME, United States

    Presented in partnership with One Longfellow Square! *also serving as the rain location Sigrid Sibley is a singer-songwriter from Poland Spring, Maine, where she was raised on a small homestead surrounded by gardens, fruit trees, and backyard chickens. Inspired by a childhood spent reading, writing poetry, and listening to her family’s music collection, she began writing

  • Square to Square Outdoor Concert Series: Toby McAllister & The Sierra Sounds

    Congress Square Park Portland, ME, United States

    Presented in partnership with One Longfellow Square! *also serving as the rain location A founding member of Sparks the Rescue, Maine native Toby McAllister has been making music since childhood. After years of touring the world with Sparks, he returned home to raise a family and launch a solo career. His debut EP Daydreamin’ (2020) led to shows alongside

  • Hip Hop in the Park

    Congress Square Park Portland, ME, United States

    Enjoy some local and touring talent! Free and family-friendly!

  • Square to Square Outdoor Concert Series: Heather Lynn + Melvin Gradiz Band

    Congress Square Park Portland, ME, United States

    Presented in partnership with One Longfellow Square! *also serving as the rain location Heather Lynn creates music that melds humor, nostalgia, and vulnerability. With a deep love of curiosity, Heather’s songs move through different genres and textures. Her performances have been compared to the likes of Patsy Cline, Weyes Blood, and Feist. Heather currently lives in

  • Old Time Music Group

    Congress Square Park Portland, ME, United States

    Enjoy some folk, Americana, bluegrass -- Old Time Music! Dancing encouraged!

  • Hip Hop in the Park

    Congress Square Park Portland, ME, United States

    Local and regional talent! Family-friendly!

  • Tender Table Night Market

    Congress Square Park Portland, ME, United States

    We're so delighted to welcome back the Tender Table BIPOC Night Market! Enjoy tons of food, art, and community. Rain date: September 20th