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*Please note – While we make every effort to crosscheck links and event details, we always encourage you to do the same before making final plans. If details are missing or incorrect, please let us know so that we can correct them. Thanks for your help! 

  • Carnival – Annapolis Mall

    Westfield Annapolis Mall 2002 Annapolis Mall Rd, Annapolis, MD, United States

    Come and discover the excitement at the largest carnival in town, happening from June 4 to June 14, 2026 at Annapolis Mall, Annapolis, MD! Brace yourself for heart-racing rides, fun […]

  • Homestead Gardens Beer Farm

    Homestead Gardens Beer Farm
    Homestead Gardens - Davidsonville 743 W Central Ave, Davidsonville, MD, United States

    Our state-of-the-art ten-barrel brewery and inviting TapRoom, featuring both indoor and outdoor seating, provide the perfect setting for relaxation and connection.

  • FREE Car Show + Live Music

    FREE Car Show + Live Music
    The Boathouse at Anchored Inn 604 Cabana Blvd, Deale, United States

    Bring your classic, hot rod, muscle car, truck, motorcycle — or just come walk around and check them all out. Live music: 5–8 PM!

  • Paca Girlfriends Party 2026

    William Paca House and Garden 186 Prince George St, Annapolis, MD, United States

    Shop in our festive marketplace, meet and greet with local designers, and connect with a wide network of influential women.

  • Dinner Under the Stars 2026

    Dinner Under the Stars 2026
    Annapolis Annapolis, MD, United States

    Enjoy cafe dining from fabulous restaurants, live music and dancing in the street every Wednesday evening 5-10pm May 20th thru September 30th. Saturday night concerts one night per month. Bring a lawn chair and enjoy a FREE concert each night!

  • Wine Down Wednesday

    Wine Down Wednesday
    The Resin Room 209 West Street, Annapolis, United States

    Wine Down Wednesday - the ultimate midweek stress reliever! Come break glass, literally! Because sometimes the best therapy is wine and broken glass and Wednesdays deserve a little sparkle!