Middletown High School

It has been expanded at least four times since then.

• Name — Middletown High School • Address — 30 Gardner Ext Ave • City — Middletown, Orange County, New York • Zipcode — 12302 • Website — https: mhs.middletowncityschools.org/ • District — Enlarged City School District of Middletown • Principal — William Donohue • Staff — 140 • Fundingtype — Public • Schooltype — high school • Grades — 9-12 • Language — English • Communities — * Middletown • Town of Wallkill (part) • Town of Wawayanda (part) • Feeder Schools — Twin Towers Middle School, Monhagen Middle School • Mascot — Bear • Team Name — Middie Bears • Colors — Blue and white Bluewhite • Rivals — Port Jervis High School, Newburgh Free Academy, Pine Bush High School • Enrollment — 2,551 (2023-2024)

Enrollment at Middletown High School was 2,551 students As of 2024. The student body was made up of 1,565 Hispanic students, 594 black students, 247 white students, 52 Asian students, and 85 students of two or more races. The school is classified as an inner city district and high poverty district, with every student registered for free lunch. Middletown had 193 full-time teachers, with a student-teacher ratio of 13 to 1. Average class size at Middletown was roughly 24.

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 game is an alternating home-and-away series and started in 1897. Middletown leads the series 72-58-7 as of 2015, and has won three of the last four games. Beginning in 2014, the game is on the list of U.S. Marines Great American Rivalry games. Middletown's boys basketball team is highly regarded in the state, and during the 2011–2012 school year the team went to the final four of the state playoffs. The Middies returned to the playoffs in 2015–2016, making the state finals and losing to Aquinas Institute. The team has a rivalry with the Newburgh Free Academy Goldbacks from nearby Newburgh. Middletown's track and field team is nationally recognized and has produced a number of successful college athletes and state and national qualifiers. 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.

• Aaron Tveit – actor • Mike Avilés – baseball player • M. Paul Friedberg – landscape architect • Benjamin A. Gilman – former U.S. Congressman and Chairman of the United States House Committee on Foreign Affairs • Kendrick Ray – basketball player for Maccabi Tel Aviv • Joseph J. Romm – scientist • Omari Spellman – NBA player for the Atlanta Hawks, attended for ninth grade