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.  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 – December 2023

September 30 – October 1, 2023 – Chesapeake Film Festival – Events are held at the Avalon Theater, Academy Art Museum, and Ebenezer Theater in Easton, MD.

October 5 – 8, 2023 – 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, Maryland.

October 7, 2023 – Taste of Cambridge – Cook-off contests, local spirits tastings, a Kid’s Zone, community performances, a vendors market, and live music in downtown Cambridge. Cambridge, Maryland.

October 7, 2023 – A Taste of Chesapeake City – A variety of the best foods Chesapeake City has to offer. Held at the North Side Chesapeake City Fire Department. There will be live music plus food (and drink) and craft vendors. The event is free to attend. Chesapeake City, Maryland.

October 12 – 15, 2023 – 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, Maryland.

October 14, 2023 – Baltimore Running Festival – Runners have a variety of distances to choose from. Courses for 5K, 10K, Half Marathon, and Marathon wind through the Inner Harbor waterfront area, historic Federal Hill, and charming Fells Point. Baltimore, Maryland

October 27 – 29 – Schooner Sultana Downrigging Weekend Tall Ship and Bluegrass 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 10 – 12, 2023 – 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 12, 2023 – Chesapeake Bay Bridge Run/Walk – This 10K course crosses the eastbound span of the Chesapeake Bay Bridge from Anne Arundel County to Kent Island. There’s a big post race party for participating runners/walkers. Annapolis – Kent Island, Maryland.

November 18 – December 24, 2023 – Baltimore Christmas Market at Inner Harbor – Indoor/outdoor market in the style of traditional German Christkindl Markets. Outdoor vendors in wooden booths located around the Walter Sondheim Fountain and along the Inner Harbor Promenade will sell traditional European food, sweets, and drinks, international holiday gifts, ornaments, jewelry, and high-quality arts and crafts. A heated festival tent will houses more vendors, a food court, and an event space. Baltimore, Maryland.

November 25 – 28, 2023 – 38th Annual Easton Festival of Trees – This annual event features festively decorated Christmas trees on display and for sale, plus entertainment performed by local artists, groups and musicians, and gift items available for purchase. Held in The Gold Room of The Tidewater Inn. Easton, Maryland.

December 1 & 2, 2023 – Dickens of a Christmas 2023 – This two day event invites visitors to step back in time to the 1840’s London of Charles Dicken’s Christmas Carol. There will be carriage rides, entertainment, home tour, food, book talks, merchandise, and more. Attendees are encouraged to “dress like the Dickens”. Chestertown, Maryland.

December 9, 2023 – Chesapeake City Candlelight House Tours – 6:00pm to 9:00pm. Check in begins at Franklin Hall. Chesapeake City, Maryland.

December 9, 2023 – 41st Eastport Yacht Club Lights Parade – Watch lighted boats parade along Spa Creek and Annapolis Harbor. 6:00 p.m. to 8:00 p.m. Popular viewing locations include Spa Creek Bridge, Naval Academy Seawall, City Dock, and any street in downtown Annapolis that ends at the water. Annapolis, Maryland