LOCAL INFO
Dudley is based out of Cambridge, Maryland on the beautiful Choptank River. Wildlife abounds in these waters and waterman still haul crabs and oysters using traditional boats. Dorchester County is the home of Harriet Tubman and there is much history to be learned here. Talbot County to the north was the home of Frederick Douglass. Oxford is a nearby port town founded in 1683 with cobblestone streets and many historic homes.
There are many events scheduled in Cambridge and Oxford in the summer season. Dudley is available to charter for viewing of boat races. Please contact Captain Woody to customize your charter.
2026 EVENTS
Log Canoe Regatta Schedule
Aug 8-9: Tred Avon Yacht Club/Chesapeake Bay Yacht Club Oxford Regatta
Aug 15-16: Cambridge Yacht Club Hicks Trophy Series
Aug 22-23: Tred Avon Yacht Club Heritage Regatta
The Cambridge Classic
May 23 - 24
The oldest active powerboat race in the country happens right here in Dorchester County, Maryland.
July 18-19 (unverified)
The Kent Narrows Racing Association hosts the 8th Annual Thunder on the Choptank.
Two great days of power boat racing.
Thunder on the Choptank
Choptank Heritage Skipjack Race
Sept 26 Choptank Heritage Skipjack Race, Cambridge MD
The annual event honors the competitive skipjack tradition, promotes maritime history, and raises funds for skipjack maintenance and preservation.
