In 2019, U.S. News & World Report ranked Medfield as the 20th best High School in Massachusetts and number 610 nationally.

Medfield's first schoolhouse was built in 1666 on the south-east corner of North Street and Janes Avenue.

This building housed students in all grades living in the center part of town and was enlarged several times over the years.

In 1879 it was named the Ralph Wheelock School and was in continuous operation until it was destroyed by fire in the early morning of March 21, 1940.

In 1957, the town accepted a gift of land on Pound Street from the Amos Clark Kingsbury family, a Medfield native, war hero and public school alum.

[7] In 2019, 94% of the high school's students earned "proficient" or higher on the Science Massachusetts Comprehensive Assessment System (MCAS).

[8] Medfield High School also prides itself on offering a wide range of honors and accelerated courses, which include 17 AP classes.

They compete in the Tri-Valley League (TVL), which includes Westwood, Hopkinton, Ashland, Holliston, Millis, Dover-Sherborn, Norton, Medway, Norwood, Dedham, and Bellingham.

In 2008, a synthetic turf baseball field was installed thanks to funding from Curt Schilling (a resident of Medfield) and donations from the Boston Red Sox, next to the middle school.