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. This includes events for Maryland’s Eastern Shore, Eastern Shore of Virginia, Southern Maryland, and Virginia’s Northern Neck, Middle Peninsula, and Hampton Roads. The calendar includes a wide variety of events including festivals, boat races, boat shows, fishing tournaments, exhibitions, seminars, and workshops.
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. Find the closest hotels.
October 3 – 5, 2025 – Mid-Atlantic Small Craft Festival – Annual celebration of small boats, featuring sailing skiffs, rowing shells, kayaks, canoes, paddle boats, prams, and more. Held at the Chesapeake Bay Maritime Museum. St. Michaels, Maryland.
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. Find the closest hotels.
October 25, 2025 – Chesapeake Bay Maritime Museum OysterFest – This popular annual festival features oysters served a variety of ways, along with other local fare, craft beer, and spirits, plus fun for the whole family with live music, an oyster stew competition, a full schedule of demonstrations and presentations, children’s activities, and more. St. Michaels, Maryland.
October 31 – November 2, 2025 – Schooner Sultana Downrigging Weekend Festival – Tall Ships, tours, music, lectures, exhibits, family activities, regional food and more. Held at Chestertown Marina. Chestertown, MD.
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. Best Easton area hotels near the Waterfowl Festival.
November 15, 2025 – Reedville Fishermen’s Museum Oyster Roast – This popular annual event is held on the grounds of the Reedville Fishermen’s Museum. Reedville, Virginia.
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.