Middletown is a city in Orange County, New York. It lies in New York's Hudson Valley region, near the Wallkill River and the foothills of the Shawangunk Mountains. Middletown is situated between Port Jervis and Newburgh, New York. The zip code is 10940, and 10941 in some cases.

Middletown grew up with the Erie Railroad and the New York, Ontario and Western Railway (among others) and attracted a number of employers, such as shoe, lawnmower blade, and furniture factories, but most of these businesses had closed by the 1960s. The closing of a large Ford Motor Company plant in Mahwah, New Jersey, and the downsizing of IBM operations in the area were a blow to the economy of Middletown and surrounding communities in the 1970s.

However, quite a few New York City police officers, firefighters and other workers moved up to the area, especially beginning in the 1970s, to purchase houses that were much less expensive than those nearer the city. These long-distance commuters have helped bolster the economy of the area. The only railroad left in town is the Middletown and New Jersey Railway.

The downtown area has a number of historic churches, and Highland Avenue has a number of large Victorian houses. Many of these are occupied by medical doctors and their families, with a section devoted to the doctor's office. Some of the largest Victorians are now used as nursing homes. There are some prosperous neighborhoods, such as Presidential Heights, but there are many less prosperous neighborhoods. The surrounding countryside was devoted partly to small dairy farms, but this has waned since the 1980s.

Middletown is the main business address for Mediacom Communications Corp and its related entities, a cable and other pay TV company. Their headquarters building is actually located outside the city in the Town of Wallkill.

Shopping in the area includes the Galleria at Crystal Run, a mall just East of Middletown, and a long retail strip along Route 211 on the East side of town. The city also has movie theaters, the historic Paramount Theatre, a local arts council, bowling alleys, WALL and WOSR radio stations, Thrall Library, and good choices for hiking, biking, and country drives nearby. There is also active participation in Boy Scouts of America and Girl Scouts of the USA, Lions Club, Elks Club, Kiwanis, Rotary Club and other service clubs. The Rotary Club runs an annual Horse Show at Fancher Davidge Park each fall.

Orange County Community College is located in Middletown (and includes the beautiful Webb Horton House, more commonly known as Morrison Hall), as is Horton Memorial Hospital and the Middletown Psychiatric Center (a major employer). The local newspaper is called the Times Herald-Record, the first cold press offset daily in the country. Middletown is also home to the Orange County Fair each summer. The Highland Lakes State Park is the nearest State Park. Another historic place in Middletown is the Hillside Cemetery, which was designed by Calvert Vaux, who co-designed New York City's Central Park w/ Frederick Olmsted.

Retail businesses in Middletown are often referenced in the phone calls of The Jerky Boys, including the Route 211 Taco Bell in "Civil War Memorabilia" (Part 2) from The Jerky Boys 3, the Middletown Motel and International Golf Discount in "What's Wrong With This World" from 2000's The Jerky Tapes.