Middletown High School serves 9th through 12th grade students in the Enlarged City School District of Middletown, which covers that city as well as adjacent portions of the towns of Wallkill and Wawayanda in Orange County, New York, United States.

The Middletown Middies football team shares a historic rivalry with the Port Jervis High School Red Raiders, named the Erie Bell game after the trophy, which is an old railroad bell from the Port Jervis-Middletown line.

The Middies returned to the playoffs in 2015–2016, making the state finals and losing to Aquinas Institute.

The boys 4x400 meter relay team won a national championship in 2011.

Middletown's tennis program is regarded as one of the best in New York state among public high schools.