Annapolis Powerboat Show Past training boat shows Annapolis City Dock, Dock Street, Annapolis, Maryland, USA October 7 - 10, 2021 10:00 - 17:00 In October, boaters from across the country gather in the historic seaport of Annapolis to shop from all major powerboat manufacturers. Spend the day exploring a variety of new and used boat types including Bowriders, Center Consoles, Cruisers, Cuddy Cabins, Deck Boats, Power Catamarans, and many more. This is the best place to purchase boating supplies, navigation equipment, fishing gear, clothing, and marine accessories. Come for the show and leave with a lifestyle as you make side-by-side comparisons, talk to industry representatives, and see the latest in boating products and services. It is a long weekend full of boats, exhibits, shopping, drink tastings, and education.