Middletown can be reached from New York City by bus and is located near the intersection of Interstate 84 and NY 17 (the future Interstate 86). State routes 17M and 211 run right through the city, and US 6 parallels I-84 to the south.

The Middletown-Town of Walkill station on Metro-North Railroad's Port Jervis line is located nearby in the Town of Walkill, and provides rail service to Port Jervis, other communities in Orange and Rockland Counties and Bergen County, New Jersey, Hoboken and New York City via a transfer at Secaucus, New Jersey.

As of the census of 2000, there were 25,388 people, 9,466 households, and 5,963 families residing in the city. The population density was 1,907.1/km?(4,939.5/mi?. There were 10,124 housing units at an average density of 760.5/km?(1,969.7/mi?.

There were 9,466 households out of which 34.0% had children under the age of 18 living with them, 40.0% were married couples living together, and 37.0% were non-families. 30.0% of all households were made up of individuals and 12.3% had someone living independently who was 65 years of age or older. The average household size was 2.62 and the average family size was 3.27.

In the city the population was spread out with 27.8% under the age of 18, 9.4% from 18 to 24, 31.0% from 25 to 44, 19.9% from 45 to 64, and 12.0% who were 65 years of age or older. The median age was 33 years. For every 100 females there were 93.4 males. For every 100 females age 18 and over, there were 90.1 males.

In the past 10 years the Middletown public school system has moved away from numerous neighborhood schools and combined more students into fewer Magnet schools. There are four elementary schools, each covering various grade levels from Kindergarten through fifth grade. Maple Hill Elementary is currently housing grades two through five. Truman Moon Elementary is currently Kindergarten and First Grade. Mechanicstown Elementary is grades two through five. Chorley Elementary houses Kindergarten and First grades. In 2005, the Middletown School District implemented a full day Kindergarten program at the request of the Middletown voters. There are two Middle schools in the District, Twin Towers Middle School and Monhagen Middle School. Middletown High School is the only building for High School and includes grades nine through twelve. There are also a number of Catholic schools.

Middletown High School offers many programs in addition to the basic educational classes found in most schools. The Middletown High School has a large and active sports program including Football, Baseball, Basketball, Tennis, Swimming, Track and Field, Soccer, Field Hockey, and various other athletic programs, as well as various other after school academic and social programs and activities. The High School also offers a Naval Junior Reserve Officer Training Corps program.

• Slate Hill
• Pine Bush
• Circleville
• Otisville
• Port Jervis
• Monroe
• Mount Hope
• Wawayanda
• Minisink
• Town of Wallkill
• Newburgh

• Samuel Beakes
• Bartley Campbell (died in Middletown)
• Linda Fite
• Benjamin A. Gilman
• Loren Grey
• Michael Jantze
• Cage Kennylz (grew up mostly in Middletown)
• Shane McDermott
• Matt Morris
• Mike Remlinger
• Joseph J. Romm
• Bill Schindler
• Kurt Seligmann (died in Middletown)
• Silas Stringham
• Launt Thompson (died in Middletown)
• Spencer Tunick
• Jimmy Weinert