Live music in Annapolis, MD

ITZALL Goode and SHC Music present an evening at 49 West featuring Mutlu with special guest Noah Pierre. Expect soulful, folk-rooted songwriting with touches of R&B and Americana. Mutlu, a Philadelphia artist steeped in the city’s soul tradition, built his career from local clubs to national and international tours. He first hit the road opening for Joe Jackson, then crossed the U.S. and Europe with Amos Lee and later supported Daryl Hall & John Oates on a theater tour. His releases range from the Manhattan Records album Livin’ It to independent projects including Good Trouble, alongside multiple appearances on Live From Daryl’s House. He is known for a smooth, emotive voice that unites influences from soul, reggae, world music, and folk. DMV-based songwriter Noah Pierre brings an intimate, acoustic set that puts the spotlight on strong songs, clear vocals, and unfussy arrangements, well suited to listening rooms and songwriter-focused spaces. Tickets are $20 online and $25 at the door. Buying in advance serves as your reservation, so there is no need to call the venue.

Reynolds Tavern hosts an evening of live jazz with the Unified Jazz Ensemble, set in the 1747 Pub while the main dining room offers an elevated dinner service. There is a $10 cover for the music, waived for guests who choose the fine dining menu. Casual dishes are available in the pub. The experience brings together dining, jazz, and a historic atmosphere in one place.

Sean Hayes appears at Rams Head On Stage with Etienne de Rocher (Haunted Shed). The San Francisco Bay Area singer-songwriter is known for a gritty mix of folk, soul, and roots influenced by R&B, pairing a gravelly, soulful voice with intimate storytelling and rhythms that invite movement. He has collaborated and toured with Aimee Mann, Frazey Ford, Charley Crockett, Jolie Holland, The Wood Brothers, Ani DiFranco, and The Cold War Kids, with remixes by house DJ Mark Farina and features on NPR, NBC, and HBO. Hayes performs in solo settings as well as with a full band. This event is open to all ages.

SHC Music Tribe presents an evening of songs at 49 West Coffeehouse, Winebar, and Gallery in Annapolis, MD with Marc Douglas Berardo and Walt Wilkins. Wilkins is a Texas-based songwriter, singer, guitarist, and producer whose work blends country, folk, blues, acoustic rock, and Texas roots. His songs have been recorded by artists such as Kenny Rogers, Ricky Skaggs, Ty Herndon, Kimmie Rhodes, and Pat Green, and a Balsam Range recording of his song Trains I Missed received an International Bluegrass Association song of the year nomination. He has produced records for Brandon Rhyder, Pat Green, Jamie Richards, Sam Baker, Bonnie Bishop, and Tina Wilkins, spent several years writing for BMG Nashville, appeared on the TV series Troubadour Texas, and earned a star on the South Texas Music Walk of Fame. Berardo is a seasoned performer known for sharp storytelling, deft guitar work, and a warm rapport with audiences. His songs have been recognized at festivals including Rocky Mountain Folks, Telluride, Kerrville New Folk, Suwannee, and Wildflower, and he has played respected venues such as the Bluebird Cafe, The Towne Crier Cafe, Narrows Center for the Arts, and more. Highlights include his 2024 album The Beauty of This Now, recorded in Austin with producers Ron Flynt and Walt Wilkins, a feature story in Ink Magazine, a headline set at the 40th Tucson Folk Festival with Abbie Gardner, and a Rammie Award for Best Show of the Year at Ramshead OnStage. Advance tickets are $20 plus fees, and admission at the door is $25. For questions, email shcmusictribe@gmail.com.

Brett Dennen brings Art Is Life to the stage with the reflective songwriting that has defined his career. The California singer songwriter recently released his eighth solo album, If It Takes Forever, a collection shaped by a year of notes, voice memos, and quiet reflection after the loss of his father. Recorded quickly with his live band and producer Jon Solo, the music pairs intimate lyrics and warm acoustic textures with touches of dusky Americana, harmonica-driven blues, rootsy indie, and contemplative folk rock. Songs such as In the Garden, Wood Canoe, Another Day in Babylon, Chipping Away, Dharma Baby, and Star Surfer explore love, resilience, and the search for meaning through vivid imagery and layered arrangements. Since his 2004 debut, Dennen has built a devoted following through steady touring with artists like John Mayer, Jason Mraz, and G Love and Special Sauce, plus notable TV placements including Parenthood and the theme for About A Boy, and he has earned multiple AAA radio top 10s, with See the World reaching No. 4 in 2021. This event is open to all ages, and it centers on the idea that art can transform life’s hardest moments into something worth celebrating.

Leftovers is a party held on the rooftop.

Mac Heat takes the stage at Annapolis Smokehouse and Tavern for one of their final Annapolis gigs of 2026. This appearance is among the last chances to see the band in Annapolis this year.

Southern Culture on the Skids appears with Poi Rogers for an all ages show highlighting the band’s playful mix of rock and roll, surf, country, folk, rockabilly, and R&B. Rick Miller on guitar and vocals, Mary Huff on bass and vocals, and Dave Hartman on drums have been at it for decades, taking their music from North Carolina house parties to late night TV, international stops near Mt. Fuji, and even shows inside state correctional facilities. They have shared stages with artists such as Link Wray, Loretta Lynn, Hasil Adkins, and Patti Smith, and their songs have surfaced in movies, television, and advertising, even drawing a parody from Weird Al. Critics have praised the biting guitar work, irresistible rhythms, and party-ready spirit of their concerts, with outlets like Rolling Stone noting the unrestrained energy of their live set. Their latest full length, At Home with Southern Culture on the Skids, arrived in 2021 after being recorded while off the road, and features Run Baby Run, a burst of garage grit powered by Mary Huff’s urgent vocal.

A lively Oktoberfest gathering in the Biergarten features Elena on accordion, filling the scene with upbeat melodies and a festive atmosphere.

Celebrate Oktoberfest in the Biergarten at Old Stein Inn with live accordion music from Elena. Enjoy lively melodies in a friendly Biergarten setting as Elena provides the soundtrack for the festivities.