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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! 

  • Naptown Social Stroll

    Naptown Social Stroll
    24 Market Space 24 Market Space, Annapolis, United States

    If you're looking for a fun, low-key way to get outside, meet people, and explore Annapolis, the Naptown Social Strolls are exactly what they sound like — and then some. These community walks bring locals together for a stroll through the streets and neighborhoods of Annapolis, with the focus on connection just as much as […]

  • Naptown Flea

    Naptown Flea 24 Market Space, Annapolis, United States

    Expect vintage clothes, jewelry, local finds, and plenty of gems waiting to be discovered.

  • 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 […]

  • 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 games, tasty food, and lasting memories. Make sure you’re part of the fun—mark your calendars and bring your family for a day full of joy […]

  • Breathwork at Arpella

    Breathwork at Arpella
    Arpella Physical Therapy & Performance 1454 Baltimore Annapolis Blvd, Arnold, United States

    Whether you're brand new to breathwork or looking to deepen your practice, this series offers practical tools you can use every day.

  • First Exposure

    First Exposure
    AND Creative Studio 1851 McGuckian Street #Suite B, Annapolis, United States

    Join photographer Kaitlyn McQuaid for "First Exposure," a 4-week digital photography workshop covering the foundations of photography.

  • 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 games, tasty food, and lasting memories. Make sure you’re part of the fun—mark your calendars and bring your family for a day full of joy […]

  • Tots @ 10:00 at Annapolis Town Center

    Tots @ 10:00 at Annapolis Town Center
    Annapolis Town Center 1906 Towne Centre Blvd, Annapolis, MD, United States

    Annapolis Town Center will begin hosting a monthly program focused on families with pre-school aged children. Tots@10:00 will be scheduled the third Tuesday of the month, April through October – 10am to noon – with a different theme each month. Activities for children in attendance will be hosted by our local business partners.