It lies in New York's Hudson Valley region, near the Wallkill River and the foothills of the Shawangunk Mountains.

It grew in the 19th and early 20th centuries as a stop on several lower New York State railroads, attracting several small manufacturing businesses.

Many residents also work at the Galleria at Crystal Run, Walmart, Media Communications Corp, and Garnet Health in the nearby Town of Wallkill.

Middletown grew through the 19th century, stimulated by construction of the Erie Railroad and the New York, Ontario and Western Railway[5] (among others).

The Webb Horton mansion and adjoining 18 acres were donated to establish Orange County Community College in 1950.

[7] In the 1970s, the economy of Middletown and surrounding communities suffered additional blows due to the closing of a large Ford Motor Company plant in Mahwah, New Jersey, and the downsizing of IBM operations in the area.

The population has continued to grow into the 21st century, while the economy has shifted largely to service and retail, with a regional medical center a major employer in the area.

Also in the Town of Wallkill, the Galleria at Crystal Run opened in the early 1990s, and in 2001 a Wal-Mart Supercenter replaced the Orange Plaza mall.

Highland Avenue is lined with large Victorian houses, some of the largest of which are now used as nursing homes.

Middletown is the main business address for the newspaper Times Herald-Record and its owner, Local Media Group.

[10] Mediacom Communications Corp, a cable and other pay TV company, is headquartered outside the city in the Town of Wallkill.

[11] The downtown area, particularly North and Main streets, has a variety of ethnic eateries and various small boutiques and thrift shops.

The city has the single-screen, 1,100-seat Paramount Theatre, which also offers stage shows and concerts, a local arts council, a bowling alley, WALL and WOSR radio stations, Thrall Library and the Van Duzer Historical Society museum downtown.

The Rotary Club runs a Horse Show at Fancher Davidge Park each fall.

The J. W. Chorley Elementary School, designed by the American architect Paul Rudolph, was built in the 1960s and demolished in 2013.

[13] ORMC was completed in 2011, merging the faculties of the former Horton Medical Center and Arden Hill Hospital.

The Middletown-Town of Wallkill station on Metro-North Railroad's Port Jervis line is located nearby, in the Town of Wallkill, 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.

A fire chief and three assistants are elected every three years by members of the city's engine companies.

A corporation counsel, commissioners of public works and of assessment and taxation, a city clerk, registrar and a treasurer and any other officers required are appointed annually by the mayor and confirmed by the common council.

Its campus includes the historic Webb Horton House (pictured), more commonly known as Morrison Hall.

Adelphi University offers a Hudson Valley Center located on the SUNY Orange campus.

[26] Touro College of Osteopathic Medicine opened a Middletown Campus, in 2014, located in the former Horton Hospital.