Marblehead Yacht Club holds several regattas each summer including the Clemson Chase Race and the Downeast Challenge.  During the Covid-summer of 2020 we started the Bakers Island Time Trial to allow boats to race in a covid-friendly setting (by themselves sailing whenever they like).  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

Clemson Chase Race
August 29, 2021
Downeast Challenge
Marblehead to Boothbay
July 30-31, 2021


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

Downeast Challenge is an exciting 100 mile long distance overnight sailboat race from Marblehead to Boothbay Harbor, 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

Bakers Island Time Trial
June 1 - Labor Day, 2021

The Bakers Light Time Trial is a self-timed ‘Round the Island’ style distance race. Boats sail a predetermined course, at their convenience, and record their own start and finish times which will be posted on Regattaman.  It can be run at any time during the specified period…you pick the day, wind, tide conditions, crew and beer. Register at