Eaglebrook School has a rich tradition in snow sports.  Many of our skiiers have gone on to achieve collegiate, national, and international fame.  Today, both alpine skiing and snowboarding is enjoyed at the competitive and recreational levels.  Eaglebrook School owns and operates the on-campus Bob Easton Ski Area on Mount Pocumtuck equipped with the George Macomber Chair Lift, state of the art snowmaking, and a powerful pack-master snow groomer with tillers.  Boys have a wonderful opportunity to learn a sport which will provide a lifetime of enjoyment.  Students have the opportunity to improve their skills and progress onto a competitive team.  Eaglebrook School has hosted the New England Division I Prep School Championships and has students competing in numerous United States Skiing Association and United States Snowboarding Association sanctioned events.

The Eaglebrook School Ski Club was founded in 1923 as the first such club at the lower school level in the United States.  While the Eaglebrook School Ski Club was pioneering the sport for younger boys, America was just beginning to take a rela interest in the sport nationally.

The program has received strong support from both faculty members, alumni, and parents.  Former faculty member Roger Langley, the "father of Eaglebrook School Skiing", was the club's first President.  In 1923 he helped organize the second Winter Carnival in the country (after Dartmouth College).  For many years Roger Langley also served as the President of both the National Ski Association and the United States Eastern Amateur Ski Association.  Former faculty member Bob Easton was responsible for major trail improvements, creating the two ski jumps, and organizing a student trail maintenance program which taught many boys life long outdoor skills and the enjoyment of physical work.  Two-time United States Olympian George Macomber, EBS '41, a current long time member of the Board of Trustees continues to be a strong supporter of the program. 

Today, the Eaglebrook School Snow Sports Program is under the leadership of faculty member Jack Shea who has contributed thirty-five years to the school.  He is a certified member of the Professional Ski Instructors of America Association and the United States Ski Coaches Association.