Middlesex is one of the top boarding schools in the US. Founded in 1901 and located in Concord, MA, Middlesex has about 350 boarding and day students. In addition to a very rigorous curriculum, the school has a great arts program and strong sports teams, especially for a smaller school. Middlesex is a member of the ISL; its rival is St. George's. Graduates go on to some of the best colleges and universities. Middlesex has some pretty famous alumni, like Steve Carrell and Bill Richardson. The school has become much more geographically diverse in recent years, and the student body now comes from all over the country and the world. The kids are really preppy, but it's still a tight-knit community where everyone works hard and knows when to kick back and relax.
The Middlesex School boys lacrosse team has won the ISL championship 7 times in 10 years.
by pudgey006 August 12, 2010
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a preppy prep school in concord massachusetts where rich kids pretend they're not rich and poor kids pretend they're rich. alot of drug use and alot of joking about being gay, which 60% of the school most likely is. 90% of the school owns ralph lauren polo shirts in at least 6 colors. the person wearing the brightest colors wins "best dressed".
hey that kid's wearing a pink shirt and lime green pants and light blue shoes, and pretending to anally rape his friend, he must go to middlesex school.
by dadada1234 December 22, 2005
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a place where you can not only find drugs and STDs, but a place where there are no real gangsters, fat chicks blocking the hallways, and the bathrooms always smell like smoke from the hard-asses when they really need a bog.
Student1: Hey, new kid, what school did you come from?

NewKid: Nowhere, just a place called Middlesex High School.

Student1: Haha! what a doof!
by Fresh_4694 January 25, 2009
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A school where when there is a snow storm and we only get a delay opening. A place where the bathrooms get locked because of people smoking in them. Where people think they’re ghetto and shit. And act all tuff. This place just ain’t it. Where the hallways smell like body odor and piss. Where people don’t know how to flush🙄
Girl: “ what school do you go to
Guy: “ Don’t laugh, but I got to Middlesex High School”
Girl: “...”
by Lmaooooo461 February 12, 2019
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