The school is 70% boarding students and 30% day students.In 2016-17, boarding students came from 30 states and 15 countries.Most of the campus buildings are located around The Circle, a grassy field at the center of the school.
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Every Wednesday morning, from to , the Middlesex community (the entire student body and faculty and staff) meets in the school chapel for a speech given by a senior on the topic of the senior's choosing.
Most speeches are given by one senior, though 'dual chapels' (chapel speeches given by two seniors) are permitted.
For the class of 2016, the mean Middlesex SAT score was 2100.
AP Art History, AP Studio Art, and AP Music Theory are offered.
A 17,000 square foot space in Middlesex School's Atkins Athletic Center serves as a tennis courts in summer and a hockey rink in winter.