Brewster's alpine ski team competes in District II of NEPSAC. Students also have the option of competing on the U.S. Ski Association (USSA) level. During the season, Brewster competes in the Lakes Region against many of the top District I independent schools in Northern New England. The ski program strives to be as competitive as possible and on an individual level, the program aims to help individual skiers develop their skills and tactics to their highest level. A number of Brewster students have gone on or will go on to race at the college level, including at Division I schools.

Brewster offers the following competitive alpine skiing:

• Independent school competition at the varsity and junior varsity level
• Optional USSA-level competition