During a trip to England, they became interested in statesman and educator William Waynflete, after whom the school is named.

In the early twentieth century, Waynflete adopted a progressive education model emphasizing physical, social, emotional, and intellectual development through hands on learning, as championed by philosopher John Dewey.

[1] Cocurricular activities such as student government and community service are offered in Middle and Upper School.

[12] Waynflete has a three-acre campus made up of historic homes modified for school use, as well as newly constructed buildings.

Waynflete also has a thirty-five-acre[14] off-campus scenic athletic complex named Fore River Fields.