125 Years of Middlesex

A new century, a new school: In 1901, on the Concord farm given to him by his father-in-law—abolitionist and Civil War   General Charles Jackson Paine—29-year-old Frederick Winsor founded Middlesex School, enlisting the Olmsted Brothers landscape architectural firm to design its campus. With the support of venerable Bostonians like General Paine, Major Henry L. Higginson, Colonel Norwood P. Hallowell, and Harvard Dean LeBaron Briggs, Headmaster Winsor set out with a mission to “send out into the community young men who are imbued with the true spirit of democracy.” This fall marks 125 years since that auspicious beginning, which Middlesex will officially celebrate on September 26, 2026.