Marblehead Yacht Club holds two regattas each summer: the Downeast Challenge and the Clemson Chase Race.  Please consider joining us in one of our races.  If you have any questions, please feel free to contact Eliot Shanabrook, chairman of the Regatta Committee at

Downeast Challenge
Marblehead to Portland
July 29-30, 2022

Downeast Challenge is an exciting 90 mile long distance overnight sailboat race from Marblehead to Portland, ME. Crewed and Shorthanded boats welcome. Rising Tide Brewing and Rumson's Rum sponsor the skippers meeting and Award party. Go for the party - enjoy the race. Rum, Beer, Trophies! Register at

Clemson Chase Race
August 28, 2022


This is a fun, low key event for captains who have little or no racing experience, as well as the seasoned racer. You will be given your own individual starting time based on your boat’s handicap. The slowest handicap boats go first and the faster boats go later. The object is for slower boats to get to the finish line before faster boats. Trophies, Beer, Caps! Register at