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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! 

  • 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 20 at Sandy Point State Park, Baygrass brings together the best in progressive bluegrass, jamgrass, and Americana in one of the most stunning settings in […]

    $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.

  • Friends of Downs Park Concert Series

    Friends of Downs Park Concert Series
    Downs Park 8311 John Downs Loop, Pasadena, MD, United States

    🎵 Friends of Downs Park 2026 Concert Series — Every Sunday, 5–7 PM Free live music, a beautiful park setting, and the Chesapeake Bay as your backdrop — what more could you ask for? The Friends of Downs Park is back with its beloved 2026 Concert Series, running every Sunday evening from 5–7 PM at […]

  • Earleigh Heights Fire Dept. Carnival

    Earleigh Heights Fire Dept. Carnival
    Earleigh Heights Volunteer Fire Company 161 Ritchie Hwy, Severna Park, MD, United States

    Earleigh Heights Fire Department Carnival July 9–18 | 161 Ritchie Hwy, Severna Park | Free Admission The Earleigh Heights Volunteer Fire Department Carnival is back! One of the most anticipated summer traditions in the Severna Park area, this 10-day carnival runs July 9–18 and is packed with rides, games, and carnival food the whole family […]

    $30
  • Muddy Creek Artists Guild Summer Artfest

    5801 Brookswood Rd. Lothian, MD 20711 5801 Brookswood Rd., Lothian, MD, United States

    The Muddy Creek Artists Guild is a roving band of intrepid artists whose mission is to support and promote the original art of southern Anne Arundel County artists. In this show, the Guild will present a professional art gallery experience, featuring a wide range of subjects and influences, from abstract to realism. You will see […]

  • 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 […]