Fall is for Festivals
Pumpkin patches, waterfront views, and small-town charm, fall in love with Annapolis & Anne Arundel County this season. Explore can't-miss events and festive happenings all autumn long.
Annapolis Boat Shows
Annapolis Powerboat Show: October 2-5, 2025. Annapolis Sailboat Show: October 9-12, 2025. Each year, Annapolis City Dock, lovingly known as “Ego Alley” transforms into a boater’s paradise as the Annapolis Powerboat Show and Annapolis Sailboat Show, presented by West Marine, cruise into town.
Great Annapolis Pumpkins
October 2025. You never know when these 1,000-pound pumpkins will pop up in downtown Annapolis, but they are hard to miss once they do! Sponsored by Visit Annapolis & Anne Arundel County and coordinated through the Downtown Annapolis Partnership, these gigantic gourds make for the perfect fall...
