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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 […]

  • Cars & Coffee

    Cars & Coffee
    Annapolis Harbour Center 2512 A Solomons Island Road, Annapolis, MD, United States

    Every Sunday, year-round enthusiasts of all makes and models gather to chat and enjoy each other’s cars. 

  • Annapolis RUN for The Light House – Half Marathon | 5K | Walk

    Quiet Waters Park 600 Quiet Waters Park Road, Annapolis, MD, United States

    Scenic routes along the trails of Quiet Waters Park and through the beautiful Chesapeake Bay-front community of Hillsmere Shores. Race has sold out last 5 years!

  • Anne Arundel County Fair

    Anne Arundel County Fair
    Anne Arundel County Fairgrounds 1450 Generals Hwy, Crownsville, MD, United States

    Then come September, the full fair takes over Crownsville for five days. The Anne Arundel County Fairgrounds has been bringing the community together through festivals, fairs, and family fun since 1952. The fair features live music, carnival rides, midway games, pig races, a petting zoo, pony rides, and performances for all ages, with hours running […]

  • Maryland Bluegrass Festival

    Sandy Point State Park 1100 E College Pkwy, Annapolis, MD, United States

    If there's one fall event worth putting on your radar, it's the Annapolis Baygrass Music Festival — and the 2026 lineup is the best yet. Taking place September 19 and […]

    $145
  • Anne Arundel County Farmers Market

    Anne Arundel County Farmers Market
    Anne Arundel County Farmers Market 275 Harry S. Truman Pkwy, Annapolis, MD, United States

    The Anne Arundel County Farmers' Market features products from local farmers, producers, and artisans year-round at our Annapolis, Maryland venue. Located at the intersection of Harry Truman Parkway and Riva Rd.

  • Anchors + Artisans Pop-Up Market

    Anchors + Artisans Pop-Up Market
    Annapolis Town Center 1906 Towne Centre Blvd, Annapolis, MD, United States

    Visitors will enjoy shopping handmade products from 50+ makers, artists, and creatives from the local community, and rotating entertainment from face painting, games on the green, live music, and build your own bouquet bars.