In 1901, Frederick Winsor opened his school in Concord. Middlesex, named for the Massachusetts county in which it is located, was to be different from the other academies and "church schools" of the day. Mr. Winsor wanted his school to be non-denominational, where students from different religious backgrounds could learn together. From the very beginning, his mission was "to find the promise that lies hidden" in every student.

The design for Middlesex's campus was created by the sons of Frederick Law Olmsted, the greatest landscape architect of the 19th century and the designer of New York's Central Park, Boston's Emerald Necklace and Stanford University. The architect for the main buildings was the noted Boston firm of Peabody & Stearns, and much of the campus that seems so familiar today was built largely by 1925.

One of Winsor's greatest achievements was the creation of the National Scholarship Program, the first of its kind at any secondary school. These scholarships brought students from every corner of the country and made Middlesex a truly national institution. This broad representation has been a hallmark of Middlesex and continues today, with current Middlesex students representing 22 states and 11 foreign countries.

From the School's earliest days, Middlesex enjoyed a close affiliation with Harvard University and, indeed, for many years the majority of Middlesex graduates attended Harvard. Today, Middlesex graduates matriculate at a large number of the country's finest colleges and universities; the largest numbers of graduates of the last four years now attend Brown, Harvard, Cornell, Tufts and Trinity.

Music and drama have always had a central role in the life of the School. For nearly 50 years, Middlesex was renowned for its performances of Gilbert & Sullivan musicals. The youngest boys in the School were cast in the female roles! Today, almost one quarter of the student body sings in one of the choruses; large numbers of students take instrumental lessons and play in musical groups; and the theatrical productions (usually one major drama and one musical each year) are of a quality not usually seen at the high school level.

Athletics, too, have always been a hallmark of Middlesex. In the earliest years, faculty often suited up for games alongside the students! For the better part of six decades, the athletic offerings were simple: nearly all of the boys played football in the fall and ice hockey in the winter, and had a choice of baseball or crew in the spring. Over the years, more sports were added and the roster has grown considerably. Middlesex now fields 24 varsity sports, and has achieved an unusually successful record for a school of its small size. in 2003, Middlesex teams won league championships in football and field hockey, and three Middlesex seniors were honored as Boston Globe All-Scholastic Award winners in their sports (football, field hockey, and girls' soccer).

Among Middlesex's many traditions, one has remained virtually unchanged since the first graduate received his diploma in 1904: every graduate has carved a plaque that permanently adorns a wall of one of the School's main buildings. Students have always been given great latitude in the subject matter of their carvings, and the plaques are full of representations of home states, favorite sports, meaningful experiences, and even rock album covers. But carving a plaque is a graduation requirement and more than a few students over the years have spent the night before Commencement applying the final coat of varnish on their plaques!

In its century-long history, Middlesex has been led, remarkably, by only five individuals, and this longevity in leadership has been a great strength and hallmark. Winsor was followed by Lawrence "Monk" Terry, who served as Headmaster from 1937 to 1964. David Sheldon was a member of the Middlesex faculty when he was tapped to be the third Headmaster. During Sheldon's tenure, the School became coeducational (in 1974) and began admitting students of color. While Deirdre Ling was the fourth Head, Middlesex constructed a number of new facilities, added a non-Western language (Chinese) to the curriculum, wired the entire campus for technology, and exuberantly celebrated the School's centennial. In 2003, Kathleen Carroll Giles became fifth Head of School.

Click here to see an early Middlesex "family tree"