Brewster is a part of the Lakes Region League as a part of the New England Prep School Association. Brewster has a rich and deep history of hockey dating back almost 200 years. 2020 will mark Brewster's 200th graduation. The hockey program's main goal is to develop players to reach their full potential. Brewster graduates have gone on to play at the junior and collegiate level, both at the Division I and Division III levels.