During the 1960s and 1970s, Coach Jackman Stewart made Berkshire one of the premier soccer programs in New England. As a fitting tribute to his remarkable career at Berkshire, the New England Prep School Soccer Association has named the New England Class A Championship Trophy, the Stewart Cup, in his honor. The proud winning tradition and passion for the game of soccer that Jackman Stewart cultivated in his players has remained a trademark of Berkshire Soccer over the years and continues today. Berkshire annually competes at the championship level, winning the Class A title in five of the past seven years, in 2012, 2013, 2014, 2016, and 2018 while earning the No. 1 ranking among the nation's prep schools.
All of the coaches in the program remain committed to the development of each player and the success of each of the three teams in the boys program. With daily training sessions, a competitive match schedule, and an overall commitment to excellence, Berkshire has been able to remain a leader in the New England Prep School Soccer Association.
In preparation for each season, Berkshire takes a preseason trip, during which the players not only get a full soccer experience but also a valuable cultural experience. In recent years, the team has taken trips to Costa Rica, England, Germany, South Africa, Spain, Sweden, Zambia and to various locations throughout the United States.
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