The trophy was given by Annette Hollis Brewster, Marion Brewster, Horatio H. Brewster, Jr. and James H. Brewster in 1965 to commemorate Mr. Brewster, Sr.'s great interest in the New Bedford Yacht Club and his love of sailing. The large oval silver tray is embellished with the Brewster house flag and the New Bedford Yacht Club burgee. In 1996, it was amended to be awarded to a race held on the New Bedford Yacht Club annual cruise. Starting in 1998 the Horatio H. Brewster Memorial Trophy has been awarded to the overall winner of the Family Regatta. The event consists of two pursuit races. First, from Padanaram Harbor to Cuttyhunk Island - to be held on Saturday, June 13th, with a 10:00 AM start. The fleet will return from Cuttyhunk to Padanaram with a race on Sunday, June 14th, starting at 1:00 PM. Every entrant that starts and finishes the race will receive an NBYC souvenir Prizes are awarded for 1st, 2nd, 3rd and 4th place for each of the two races. The overall winner will be awarded the Horatio H. Brewster Trophy.