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  • The War and Treatyy

    Rams Head On Stage 33 West Street, Annapolis, MD, United States

    For the past decade, soulful duo The War And Treaty—the husband-and-wife team of Michael and Tanya Trotter—have released music that continues to elevate them beyond beloved industry favorites, as well […]

  • Mike Tramp of White Lion (solo acoustic)

    Rams Head On Stage 33 West Street, Annapolis, MD, United States

    Mike Tramp, legendary White Lion singer, songwriter and front man stepped out on his own in 1995 and began his 29-year long solo career. With twelve consistent solo albums to […]

  • Trevor Hall

    Rams Head On Stage 33 West Street, Annapolis, MD, United States

    Raised on the coast of South Carolina, Trevor Hall discovered early on that music wasn’t just a passion—it was a calling. At sixteen, he recorded his first album and soon […]

  • Jon McLaughlin: Home For The Holidays

    Rams Head On Stage 33 West Street, Annapolis, MD, United States

    Ring in the season with Jon McLaughlin’s Home for the Holidays, an evening of music, stories, and holiday cheer. Jon returns to the stage with his signature blend of heartfelt […]

  • Bay Winds Band Winter Concert 2026

    Bay Winds Band Winter Concert 2026
    Unity by the Bay 4 Pointless Forest Trail, Annapolis, MD, United States

    Join the Bay Winds Band for our 2026 Winter Concert Series "What's in a Word" "What's in a Word."  Half-and-half program. The non-holiday half explores works that capture one-word ideas.  […]

    $10

  • Annapolis Chocolate Binge Festival

    Inner West Street Annapolis, Maryland

    About This Event A festival celebrating chocolate! The Inner West Street Association brings you the popular Annapolis Chocolate Binge Festival to downtown Annapolis for the holidays. On Sunday, December 6th […]

    $6 – $70

  • First Sunday Arts Festival

    First Sunday Arts Festival
    Annapolis, 60 West St, 60 West Street, Annapolia, Maryland

    First Sunday Arts Festivals - Where Community and Arts FuseA monthly (May to November) street festival on the first Sunday of the month featuring 130 local and regional artisans, live […]

    FREE

  • Elizabeth Cook (matinee)

    Rams Head On Stage 33 West Street, Annapolis, MD, United States

    Elizabeth Cook is a Nashville-based singer songwriter from Wildwood, Florida. As a critically acclaimed live act and recording artist, The New York Times lauds her “a sharp and surprising country […]

  • Bay Winds Band Winter Concert 2026

    St. Martin's Lutheran Church 1120 Spa Road, Annapolis, MD, United States

    Join the Bay Winds Band for their 2026 Winter Concert Series "What's in a Word" "What's in a Word."  Half and half program.  Non-holiday explores works that capture one-word ideas.  […]

    Free

  • Mindi Abair: I Can’t Wait For Christmas

    Rams Head On Stage 33 West Street, Annapolis, MD, United States

    Mindi Abair’s I Can’t Wait For Christmas Tour is bringing the spirit of the holidays to audiences across the U.S. for an exciting, heartfelt season of music—now in its third […]

  • Tab Benoit w/ Bonerama: Blues and Brass Winter Tour

    Rams Head On Stage 33 West Street, Annapolis, MD, United States

    Tab Benoit is a 4x Grammy nominated singer, songwriter and guitarist who has built a remarkable 30+ year career on the foundation of his gritty and soulful Delta swamp blues, […]