Chesapeake Bay Region Calendar of Events: October – December

Chesapeake Bay Region Calendar of Events: October – December

October – December, 2024 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 3 – 6, 2024 – 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 5 & 6, 2024 – Crawlin’ Crab Half Marathon & 5K – Featuring a flat, fast course and a fun celebration afterward. Hampton, VA.

October 10 – 14, 2024 – 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

November 1 – 3, 2024 – 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 8 – 10, 2024 – 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.

November 23, 2024 – Norfolk’s Grand Illumination Parade – The Grand Illumination Parade is a Norfolk tradition that has been going on for years on the Saturday before Thanksgiving. The parade travels through the streets of downtown Norfolk and ends along Waterside Drive. Norfolk, VA.

November 23, 2024 – Coliseum Central Whimsical Winter Wonderland – Hampton Coliseum is transformed into a festive wonderland with fun for the whole family. This free event features stage shows by aerialists, jugglers and illusionists in addition to roaming entertainers and stilt walkers. There will be ample opportunities for photos in the various photo booths and holiday-themed areas. In addition, there will be face painting, balloon and glitter tattoo artists. Hampton, VA.

Norfolk 23 – 24, 2024 – 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.