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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! 

  • 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!

  • Annapolis Powerboat Show

    Annapolis Powerboat Show
    Annapolis City Dock Annapolis, MD, United States

    October brings the transformation of Ego Alley and Annapolis Harbor into a boater’s dream, as floating docks create a temporary marina showcasing new and premiering boats and the latest in boating accessories, equipment and apparel during the Annapolis Powerboat Show.

  • Creek Critters Nature Walk

    Creek Critters Nature Walk
    The Chesapeake Children's Museum 25 Silopanna Road, Annapolis, MD, United States

    Guided walk to look for seasonal changes in the plants and animals in the woodlands and creek outside Chesapeake Children's Museum. Price includes museum admission.

    $8
  • Food Truck Fridays

    Food Truck Fridays

    Join us every Friday evening from 4–8 PM for Food Truck Fridays in Annapolis! With 12+ food trucks serving up an amazing variety of cuisine, free admission, and fun for all ages, this is the can't-miss weekly event of the season.

  • Annapolis Powerboat Show

    Annapolis Powerboat Show
    Annapolis City Dock Annapolis, MD, United States

    October brings the transformation of Ego Alley and Annapolis Harbor into a boater’s dream, as floating docks create a temporary marina showcasing new and premiering boats and the latest in boating accessories, equipment and apparel during the Annapolis Powerboat Show.

  • Capital SUP Ladies Night

    Capital SUP Ladies Night
    Capital SUP Warehouse 7364 Edgewood Rd, Annapolis, MD, United States

    Grab your friends and kick off the weekend on the water with Ladies' Night at Capital SUP! Every Friday from 4:00 PM–7:00 PM, enjoy $15 paddleboard and kayak rentals at all Capital SUP locations.

    $15
  • Dodon ‘Til Dusk

    Dodon ‘Til Dusk
    The Vineyards at Dodon 391 Dodon Rd, Davidsonville, United States

    A relaxed yet refined evening in the vineyard, where seasonal cuisine is prepared fresh on-site and enjoyed alongside exceptional Dodon wines. Open to all guests, with families and children warmly welcome, these gatherings are held every other Friday from 4:00–8:00 PM, beginning May 8th and continuing through October. Each evening offers the opportunity to gather, linger, and savor the beauty of the season as the sun sets over the vines.