Brewster crew began in 1989 as a recreational program. Since then, it has evolved into a multi-level competitive program. Because of school size, Brewster primarily races fours. The goal of the program is to develop student athletes into cohesive crews to be competitive in the New England Interscholastic Rowing Association (NEIRA) and U.S. Rowing Association junior team ranks.

Fall crew is a long-distance season with three-mile races judged by time over distance. Crews race with a time interval between them, so there is little opportunity to know how fast you are going relative to another boat unless you get passed or you pass another. It is a grueling, mentally challenging racing season. Brewster races boys' 8's and 4's in the fall, and competes in major regattas such as the Head of the Fish Regatta and the Philadelphia Frostbite Regatta.

Spring crew is a season of 1500-meter sprint regattas, and Brewster races in boys' and girls' 4s. Boats are lined up in lanes to compete bow to bow, and crews know exactly how they're doing in relation to their competitors. It is a fast-paced race season with lots of action and intensity. In the spring, Brewster hosts the Northern New England Championships and competes in major regattas such as the Founder's Day Regatta and the NEIRA Championships.