From timeless classics to today's chart-toppers, Sunset Crossroad is a genre-blending journey through rock, pop, and country. Fueled by dynamic vocals and tight rhythms, we’re all about feel-good vibes and songs that hit the heart and the dance floor.

Free Event

6:30PM Lesson ($5 Suggested Donation)
7:30PM Open Dance

It’s all Country, all night long. Grab a beer at the bar and a little do-si-do on the floor. Are you a beginner line dancer? No problem; we offer line dancing classes starting at 6:30pm. Open dancing starts at 7:30pm and goes til 9:30pm, and Vanessa will stay and lead some line dances throughout the night. Grab your boots if you got em, or whatever you got if you don’t.

Cheryl Jeanette is a singer-songwriter and poet. Her new single “Pirate Sails” made its debut at the legendary Towne Crier in Beacon, NY this year. This song was composed on Frenchman Bay sailing around the Porcupine Islands in Maine aboard a four masted schooner named “Margaret Todd”. She will begin her solo acoustic DownEast Sunrise tour at the Deer Isle Music Hall on July 29th, bringing awareness to the new Maritime Research Center being built in Brooklin and the High Seas Treaty designed to protect and sustainably manage marine life in international waters. Her original music represents the cultural history in Maine enveloped in Maritime traditions reflecting the natural beauty and deep connections to the four elements of Nature known as Earth, Water, Fire and Air. She composes her original music in Hancock County Maine and has released EP “Spirit of the Seasons”, Albums “Down to Earth” and “Auburn Street”. Cheryl was a featured Poet/Writer at the Maine State House / Hall of Flags in Augusta Maine this year and is best known for original songs titled Brooklin, Green Island (composed off the coast of Stonington), DownEast & Sweetgrass. Inspirited by her father who was a Poet from Maine and late friend American Author E.B. White, original music by Cheryl Jeanette can be heard on all streaming platforms worldwide or by visiting her music link cheryljeanette.hearnow.com.

Award-winning Maine singer-songwriter Chris Ross is a native of Hancock and 2014 winner of the "Songwriter of the Year" award at the New England Music Awards. Known for his cinematic lyrics  and sharp humor, Ross’ wit matches his musical talent. “I try my damnedest to make you feel feelings,” he says, “ occasionally even pleasant ones.”

On this day we're also proud to support the Island Community Center by donating 10% of all food sales to help fund the incredible programs and services they provide to our community. If you're attending the Island Community Center Annual Auction, we'd love to see you afterward for great food, cold drinks, and live music featuring Chris Ross!

For more than 20 years, the Island Community Center has been a gathering place for all ages, offering youth sports, Camp Kooky, early childhood programming, fitness and wellness opportunities, community events, senior activities, and countless programs that bring our island together and strengthen our community.

Free Event

Inviting all area musicians, storytellers and comedians to join us on our welcoming stage. Whether performing or cheering on, come enjoy a night with great local talent, food and drinks. Sign up in advance at jenn@deerislemusichall.com, or sign up in person starting at 5:30pm. Time slots are 3 songs or 10 minutes total.

Abby Litman is a multi instrumentalist and folk singer songwriter based in Stonington. Since her move from Los Angeles, CA, she has immersed herself in the beauty of the island's landscape and has involved herself in the community through the after school program, teaching music lessons and starting a community chorus. 

Her most recent EP “Steady” was released in 2024. These five songs are about self-love, self-discovery and self-acceptance. They are about family, relationships, friendships and the world around us. Her songs marry the lyrical traditions of American folk music with inventive acoustic arrangements and modern concepts. 

Stonington and Deer Isle musicians bringing you live music with rhythms that will make you tap your feet, move your hips and sing along to your favorite songs.

Free Event

The Ordways are a grassroots Americana–country-rock band led by singer-songwriter Ryan Ordway and vocalist/songwriter Michelle Leclair. Their sound blends heartfelt storytelling with raw rock ’n’ roll energy—think Waylon Jennings riding shotgun in an old Ford pickup. Ryan has shared the stage with artists including Steve Miller, George Thorogood, members of Jerry Garcia Band, The Samples, and members of Matchbox Twenty—bringing a seasoned, road-tested presence to every show. Built on great songs and genuine connection, The Ordways deliver unforgettable live performances. Back on the road in 2026.

Singer Songwriter Tyler M. Walker is a country, folk, rock and roller celebrating the magic of music. With roots in blue collar New England, Tyler sings about the experiences that shaped him from an early age.

Free Event

Paddy Mills is a Maine-based folk singer and songwriter whose music carries the salt air of the North Atlantic and the stories of the people who live by it. With a voice both warm and weathered, Paddy’s songs navigate the waters between tradition and modern life —celebrating working folks, coastal communities, and the enduring pull of the sea. Mills has played coffeehouses, concert halls, schooners, ketch’s and festivals across the Northeast, earning a loyal following for his evocative songwriting and unpretentious style. His performances feel like conversations between old friends. His original songs, such as Cribbage in the Corner reflect his deep connection to Maine’s maritime culture and the people who make their living close to nature’s edge.

In 2013 Paddy won the Woody Guthrie Folk Festival Songwriting Contest as well as the Rosegarden Coffeehouse Performing Songwriter Competition. His 2014 album Race to the Bottom reached #6 on the Roots Music Report and #12 on the Folk DJ list; he won the South Florida Folk Festival Singer-Songwriter Competition, The Mid Atlantic Song Contest and the CT  Folk Folk Festival Song Competition that same year. In 2016 Paddy was chosen to play at the Falcon Ridge Folk Festival Emerging Artist Showcase. When he’s not writing or playing songs, Paddy spends as much time as he can with his wife and four kids on the coast of Maine, messing about with wooden boats.

Inviting all area musicians, storytellers and comedians to join us on our welcoming stage. Whether performing or cheering on, come enjoy a night with great local talent, food and drinks. Sign up in advance at jenn@deerislemusichall.com, or sign up in person starting at 5:30pm. Time slots are 3 songs or 10 minutes total.

Don has been performing since Hippies were a groovy thing.he has played both lead guitar and bass, in country and rock bands, presently playing with The Tim Lewis (country) Band, The Tiffany Effect (rock and country) Band, and Don Blauss and Friends (classic rock). His true wheelhouse and passion is as an acoustic singer/songwriter in the vein of James Taylor, CSNY, Dan Fogelberg. Along with a sizable catalog of covers, he also has a volume of original songs telling personal stories. Don has performed (and played hockey with) Saxaphonist Dana Colley (Morphine / Vapors of Morphine), and got Kristen Merlin (season 6 The Voice 4th place) her start. He recently relocated from Massachusetts to Maine, not far from his grandmothers Deer Island birthplace.

We will be enjoying all the festivities that the island has to offer. We will see you at the pier!

The Returnables: reunited after 30 years to make joyful noise. Classic rock, blues, and jams galore!

https://www.facebook.com/ReturnablesBand

$10 Cover

Award-winning songwriter Skip Bailey is a country and folk singer-songwriter from Maine whose songs reflect the grit, humor, and heart of rural life. He describes his work as “salt of the earth songs for salt of the earth folks,” a phrase that reflects his commitment to honest storytelling and connection to place. His music blends country, folk, and maritime influences into lyrical portraits of everyday people: fishermen, farmers, dreamers, and working folks who keep Maine’s traditions alive.

Performing across the state from Kittery to Lubec, Skip has earned a loyal following for his down-to-earth performances and his unique and powerful vocals. He currently holds a residency at Allagash Brewing Company and has played notable venues including Blue, The Apohadion Theater, Absolem, and Fogtown Brewing Company. His upcoming single, which won the 2025 Maine Songwriters Association’s 15th Annual Songwriting Contest, showcases his authentic voice and lyrical storytelling. Skip has also been featured on WERU’s Country and Northeastern radio show, joining the ranks of Maine’s next generation of songwriters carrying forward the region’s rich folk tradition.

Free Event

Island Pride- Celebrating 5 Years of Community, Pride, and Belonging.
Keynote Speakers: Representative Holly Eaton, Attorney General Aaron Frey

We are so excited to host the Deer Isle-Stonington Pride Celebration as it moves to Saturday this year. Everyone is welcome here, whether your finest is feathers and sequins or flannel and Carhart. Whether you are part of the LGBTQ+ community or an ally, put down those sneakers and get out your party clothes and celebrate!

The 2026 Pride Motorcade will take place starting at the Stonington Ballfield (40 School Street, Stonington, ME) at 2:00pm with a public motorcade around the island. The path will go through downtown Stonington, take Rte 15 to Deer Isle Village, and back up Rte 15A to the ballfield.

Join us at Deer Isle Music Hall & BBQ anytime after 4PM for good food, great community, special guest speakers and lively music. At 6PM, speakers Representative Holly Eaton and Attorney General Aaron Frey share their stories with music by Sunset Crossroad to get your booty shakin’.

ONTOLOGICS is a multi-instrumentalist duo fusing progressive rock, hip-hop, electronica and more, with an explosive live presence. Originally based in Providence, RI, the duo features singer/songwriter Ian Campopiano and drummer Andrew Morris.

Their latest release, LP IV, It's Safe To Say The Veil Is Thinning (Release Date: 2/29/24) features the return of P-NUT / Aaron Wills of 311 for the third consecutive record, and they are currently working on their fifth collaborative effort for Ontologics LP V (Tba 2026-27).

Prior to working with Ontologics on LP IV, P-NUT collaborated first on their sophomore album, on track “Primal Discourse”, and previously said of the duo, “they turned this song into like a science fiction masterpiece. And if we can’t beat that, I think we should just do a cover of their song" - P-Nut, popdose.com interview, referencing the “Go” Demo.

Multi-award-winning singer/songwriter, Jessey Adams, showcases a powerful combination sound of outlaw and traditional style country music. Embodying the spirit of a vagabond, her music has taken her across the United States to perform wherever there are neon lights and dusty floorboards. From festivals to dive bars, her music is enjoyed by many. Her original songs encompass the thrill of being on the road while still remembering a simple upbringing with small-town roots. This young Michigan native has been recognized in multiple states for her unique storytelling through songwriting. Jessey has won the overall title in both the Pensacola Beach Songwriters Festival competition (2024) and the Michigan State Fair Superstars competition (2024). She was also named a semi-finalist in the Tennessee Songwriters Week competition (2024) and a nominee for five Josie Music Awards. Jessey has opened for names such as; Dierks Bentley, Cooper Alan, John Paycheck, Sunny Sweeney, Trey Lewis, and more. With features on multiple radio and news shows and a large variety of events under her belt, this up-and-coming country singer is one to remember.

6:30PM Lesson ($5 Suggested Donation)
7:30PM Open Dance

Grab a beer at the bar and a little do-si-do on the floor. Are you a beginner line dancer? No problem; we offer line dancing classes starting at 6:30pm. Open dancing starts at 7:30pm and goes til 9:00pm. Grab your boots if you got em, or whatever you got if you don’t.

6:30PM Lesson ($5 Suggested Donation)
7:30PM Open Dance

Grab a beer at the bar and a little do-si-do on the floor. Are you a beginner line dancer? No problem; we offer line dancing classes starting at 6:30pm. Open dancing starts at 7:30pm and goes til 9:00pm. Grab your boots if you got em, or whatever you got if you don’t.

With a voice like Phil Collins and a rhythm like Johnny Cash, Justin Merle is a Portland based singer-songwriter. Justin has been composing original songs for 20 years. His content ranges from folk and country, to pop and contemporary. He has had recording sessions and gigs in much of New England and continues writing new songs to this day.

6:30PM Lesson ($5 Suggested Donation)
7:30PM Open Dance

Vanessa is back to teach line dancing to all us new-boots and returning stompers. The kitchen is closed but the bar will be open, so grab a beer or soda at the bar and a little do-si-do on the floor. Hang out, dance, have a great time shaking off the winter blues.

6:30PM Lesson ($5 Suggested Donation)
7:30PM Open Dance

Grab a beer at the bar and a little do-si-do on the floor. Are you a beginner line dancer? No problem; we offer line dancing classes starting at 6:30pm. Open dancing starts at 7:30pm and goes til 9:00pm. Grab your boots if you got em, or whatever you got if you don’t.

Thomas Hinds is a hard-touring troubadour surviving on raw talent and a heartfelt folk-rock repertoire. A singer/songwriter out of northern Georgia, Thomas has been building a reputation for lyrical depth and an original voice musically. His blues-based Americana sound has been heard from coast to coast over the last decade with a steady catalog of fresh material continually being added to his set lists.

6:30PM Lesson ($5 Suggested Donation)
7:30PM Open Dance

Grab a beer at the bar and a little do-si-do on the floor. Are you a beginner line dancer? No problem; we offer line dancing classes starting at 6:30pm. Open dancing starts at 7:30pm and goes til 9:00pm. Grab your boots if you got em, or whatever you got if you don’t.