Commodore Roscoe E. Sherbrooke was a lifelong sailor and devoted member of the Cohasset Yacht Club. Upon his death, a group of his friends donated a binnacle in his memory to be raced for in a single-handed race. The race committee has the prerogative to choose the format each year, whether the racing shall be in one-design or handicap boats.
2021: H12: Peter Pearce – Sweet Pea
2020: 210: Sean Sweeney – Mac Lir