Friends of Congress Square Park

Salsa in the Square Feat. Primo Cubano
2026-06-11 17:30 - 20:00 (America/New_York) | Congress Square Park, Portland, ME, 04101, United States
Salsa dancing is back! Enjoy a free salsa dancing lesson provided by PM Salsa at 5:30, with Primo Cubano taking the stage at 6. Free and open to all!

Hip Hop in the Park
2026-07-11 18:00 - 20:00
Organized by Monday of the Minds, featuring local talent! Family-friendly!

Square to Square Outdoor Concert Series: Portland Jazz Orchestra
2026-07-16 18:00 - 20:00
Presented in partnership with One Longfellow Square! *also serving as the rain location

The Portland Jazz Orchestra has been a staple at One Longfellow Square since 2006, bringing the sound of Maine’s premier concert jazz ensemble to our stage month after month. Led by Dr. Chris Oberholtzer, this 19-piece big band performs an ever-evolving mix of instrumental and vocal jazz, from classic charts to new works penned by local composers like Craig Skeffington, Mike Sakash, Brad Ciechomski, Jake Sturtevant, and Terry White. Their repertoire also draws from the greats, including Duke Ellington, Count Basie, Stan Kenton, Bill Holman, Patrick Williams, Woody Herman, and Maria Schneider.
The orchestra is made up of top-tier New England musicians who balance active performing careers with roles as educators. Collectively, PJO members have recorded, toured, and shared stages with artists such as Natalie Cole, Tony Bennett, Wayne Bergeron, The New York Voices, Barry Manilow, Roberta Flack, The Temptations, the Artie Shaw Orchestra, the Smithsonian Jazz Masterworks Orchestra, and the Glenn Miller Orchestra.
Grounded in their commitment to music education, the Portland Jazz Orchestra also offers clinics and performances for schools and community programs throughout northern New England.

Square to Square Outdoor Concert Series: Sunburned Sharks
2026-07-23 18:00 - 20:00
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 vocals, and airtight horn lines that punch with big-band swagger, Sunburned Sharks has drawn comparisons to Hozier’s spiritual intensity, Lake Street Dive’s horn-fueled vitality, Vulfpeck’s vacuum-seal vision, and John Mayer’s guitar finesse. The setlist might take you from Whitney Houston to Marvin Gaye, Al Green to Fleetwood Mac, Tom Petty to The Dip, Bruce Springsteen to original indie-funk fever dreams—each delivered with an energy that could power a town for a week.

Square to Square Outdoor Concert Series: Tricky Britches
2026-07-30 18:00 - 20:00
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 Britches has become a staple of the New England music scene. The band features Tyler Lienhardt on Fiddle, Seth Doyle on Guitar, Jed Bresette on Bass, Jake Henning on Mandolin, Richard Bicknell on Banjo, and Riley Kern on drums.

Square to Square Outdoor Concert Series: Sigrid Sibley + Thomas Charles Clukey
2026-08-13 18:00 - 20:00
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 songs after picking up the guitar at age 11.
An active part of the Maine music scene since 2017, Sigrid performs across the state at festivals, songwriter showcases, coffee shops, bookstores, and markets. A graduate of the University of Southern Maine’s Music Education and Composition program, she released her debut album, Old Faithful Dreams, in May 2025. The album’s first single, “Never Knew Love,” was named a finalist in the Maine Songwriters Association’s 2025 Songwriter Contest.
Thomas Charles Clukey grew up in rural Maine, where music first found him through classic country radio, school bands, and time spent singing with his dad. Though he spent years working with his hands in welding and manufacturing, songwriting remained a quiet constant in the background. In recent years, that spark has grown into a full-blown pursuit—leading to award-winning songs, local performances, and the release of his first singles as he works toward his debut album.

Square to Square Outdoor Concert Series: Toby McAllister & The Sierra Sounds
2026-08-20 18:00 - 20:00
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 some of his idols, and in 2023 he followed with Autumn Skies, a heartfelt record featuring longtime Sparks bandmates and guest appearances from members of The Mallett Brothers Band and Old 97’s. The album earned a New England Music Awards nomination for Album of the Year.
In 2024, inspired by the loss of his father and the birth of his second child, McAllister recorded The Outsider EP in rural Maine with producer Jonathan Wyman. Its opening track, “Millinocket Stars,” is now in rotation on Portland’s WCLZ. Beyond his original work, McAllister stays busy performing across New England, including with his wedding band The Jameson Four.
Toby McAllister & The Sierra Sounds have shared the stage with Carly Pearce, Eli Young Band, Rhett Miller, Old 97’s, Billy Bob Thornton & The Boxmasters, and The Mallett Brothers Band.

Hip Hop in the Park
2026-08-22 18:00 - 20:00
Enjoy some local and touring talent! Free and family-friendly!

Square to Square Outdoor Concert Series: Heather Lynn + Melvin Gradiz Band
2026-08-27 18:00 - 20:00
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 Portland, Maine where she works as a music teacher. Heather performs her original music solo and with her bandmates throughout New England.

Melvin Gradiz was born in Miami, Florida, and has been drawn to music for as long as he can remember. In recent years, he’s fallen in love with songwriting and releasing music independently. He recently formed the Melvin Gradiz Band with drummer Gary Lowell and bassist Randy Runnels and is excited to see the music that emerges from there.

Old Time Music Group
2026-09-10 18:00 - 19:30
Enjoy some folk, Americana, bluegrass — Old Time Music! Dancing encouraged!

Hip Hop in the Park
2026-09-12 18:00 - 20:00
Local and regional talent! Family-friendly!

Tender Table Night Market
2026-09-13 17:00 - 21:00
We’re so delighted to welcome back the Tender Table BIPOC Night Market! Enjoy tons of food, art, and community.
Rain date: September 20th

Talk Like A Pirate Day: Sea Shanties with The Shank Painters!
2026-09-19 13:00 - 15:00
Y’arr!
Celebrate International Talk Like A Pirate Day with sea shanties by local pirate band The Shank Painters! Family-friendly, and costumes encouraged!

Sunken Dreams
2026-09-25 19:00 - 20:00
An evening of dreamy underwater dance with ambient banjo and electronic music. Immerse yourself in the sensuous underwater dance film work of local filmmaker Juliette Sutherland, set to the ambient banjo and electronic music
of New England musicians Djim Reynolds, Nate Groth and Al Mead.

www.juliettesutherland.com https://djimreynolds.bandcamp.com/album/caretaker
