Deerfield Academy was founded in 1797 when Massachusetts Governor Samuel Adams granted a charter to found a school in the town of Deerfield. It began to educate students in 1799. The academy quickly established itself as one of the finest schools in the new republic, drawing boys from prominent families across New England. The school produced influential men that occupied many congressional and gubernatorial seats in New England. By the end of the 19th century, the shifting trends in industrialization had left rural Deerfield behind. The economic hardships of the times impoverished local farmers and drove them away to the wealthy cities. The board of trustees was considering closing the Academy, as only nine students remained. These were the school's darkest times. With little support from local farmers and a dire economic situation, the 100-year-old school was on the brink of collapse.

In the early twentieth century, Deerfield's fortunes rose with the appointment of Frank Boyden as Headmaster. He quickly reorganized the school and provided it with a sound financial basis. He recruited students actively from local farms and towns, promising parents that their boys would be successful. Boyden had great confidence in the value of athletics as a component of education. He often played on varsity squads that lacked players. He attracted and trained many teachers who would become masters and keep long loyalties to the academy. The prestige enjoyed by the school today is a direct result of the foundations he laid over seven decades, including training scores of men as teachers and headmasters in their own right. After 66 years of service, Frank Boyden retired in 1968.