Chesapeake Bay Region Calendar of Events: October – December
October – December, 2025 Calendar of Events
This is a calendar of events taking place on and around the Chesapeake Bay for the months of October, November, and December.
Return to the Calendar index page to select different months.
October 2 – 5, 2025 – United States Powerboat Show – The largest in-water boat show in the world! This popular boat show happens annual at the Annapolis City Dock, where you will find powerboats of every description, plus boating accessories, lessons, and more. Annapolis, MD
October 4 & 5, 2025 – Crawlin’ Crab Half Marathon & 5K – Featuring a flat, fast course and a fun celebration afterward. Hampton, VA.
October 9 – 12, 2025 – United States Sailboat Show – Annapolis City Dock fills with temporary floating docks lined with sailboats of all types for this annual show. There are also vendors for sailing gear and accessories, services and more. Annapolis, MD
October 31 – November 1, 2025 – Schooner Sultana Downrigging Weekend Festival – One of the largest tall ship gatherings in North America – plus a bluegrass music festival. Tall Ship sails, tours, incredible live bluegrass music, lectures, exhibits, family activities, regional food and more. Held at Chestertown Marina, Chestertown, Maryland.
November 14 – 16, 2025 – Easton Waterfowl Festival – This three-day festival brings thousands of visitors to Easton, Maryland each fall to enjoy wildlife art from renowned master artists, plus a variety of events and vendors, including retriever demonstrations, Dock Dogs competitions, goose and duck calling contests, street musicians, and Eastern Shore cuisine. Events are held at various venues throughout town. Shuttle buses are available to help you get around. Easton, Maryland.
Norfolk 22 – 23, 2025 – Norfolk Harbor Race Weekend – 5K, 10K, and Half Marathon events with courses that travel through Norfolk’s downtown, thriving art community, historic neighborhoods, and Old Dominion University’s campus. Norfolk, VA.