• Maryland Renaissance Festival

    Maryland Renaissance Festival
    Maryland Renaissance Festival, 1821 Crownsville Rd, Annapolis, MD 21401, USA

    The Maryland Renaissance Festival, a tradition for the entire family, begins its 50th season on August 29th and runs Saturdays and Sundays and Labor Day Monday through October 25th for nine …

  • First Sunday Arts Festival

    First Sunday Arts Festival
    53 West Street 53 West Street, Annapolis, United States +1 more

    Don't miss the First Sunday Arts Festival! On the first Sunday of the month, West Street and Calvert Street are closed for a family friendly festival. It has over 150 …

  • Annapolis Songwriters Festival

    Don't miss the Annapolis Songwriters Festival! Young the Giant is the headliner, and the festival will continue through September 10-13, 2026 across multiple locations! Get your tickets here! (DNML)

  • Maryland Seafood Festival

    Maryland Seafood Festival
    Sandy Point State Park 1100 E College Pkwy, Annapolis, United States

    The Maryland Seafood Festival hosts loads of seafood vendors, local shopping and vendor options, live music, a fantastic beverage selection, contests, kids activities, and more! This event will take place …

  • Fall Saturdays at Ridge Grow

    Ridge Grow 244 Old Mill Bottom Rd S, Annapolis, United States

    Fall Saturdays are coming to Ridge Grow! 🍂🎃 Every Saturday Sept. 12–Oct. 31 — pumpkins, mums, fall finds, food trucks & family fun! Bring the whole family and enjoy our playground, putt-putt, pumpkin patch, pumpkin bowling & more — all while soaking up a fall day at Ridge Grow. 🤎 Your new favorite fall Saturday …

    Free