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WRRV (92.7 FM) is a commercial radio station licensed to Middletown, New York and serving Orange County, including parts of the mid Hudson Valley and Catskills Mountains. The station is owned by Townsquare Media and broadcasts an alternative rock radio format. WRRV's programming is simulcast on 96.9 WRRB Arlington, New York which serves the Mid-Hudson Valley, north of WRRV's signal. WRRV has an effective radiated power (ERP) of 6,000 watts. Its transmitter tower is on the northwest edge of Middletown, off Monhegan Avenue. The studios and offices are in Poughkeepsie, on Pendell Road.

Middletown State Homeopathic Hospital (also known as Middletown State Hospital or Middletown Psychiatric Center) was a hospital for the treatment of mental disorders located in Middletown, New York. It opened on April 20, 1874, and was the first purely homeopathic hospital for mental disorders in the United States. The hospital, which served "mentally ill patients from Orange, Sullivan and Ulster Counties". employed a number of new techniques for the treatment of mental disorders, most notably the use of baseball as a therapy. It closed in 2006.

Oliver Avenue Bridge was a historic railroad bridge located at Middletown in Orange County, New York. It was built in 1895 by the Havana Bridge Works. It was a single span, metal trough Pratt truss structure measuring 20 feet wide and 105 feet long. The bridge has been demolished. It was listed on the National Register of Historic Places in 1984.

J. W. Chorley Elementary School was a modernist architecture school building in Middletown, New York designed by American architect Paul Rudolph while he was serving as Dean of the Yale School of Architecture. The school was torn down in November 2012.The school was built from 1964 - 1969 and included an open floor plan. It featured a "progressive" design and was built on a 27-acre campus. It was the only building he designed to serve children. The weblog inhabitat ran a feature on the destruction of Rudolph's work including Chorley Elementary and Rudolph's Sarasota High School building. In 2010, the Preservation League in New York named John W. Chorley Elementary School to its 2010 Seven to Save list of threatened properties. In 2010 the Center for Architecture held an event examining the school and plans to replace it with a parking lot. The Library of Congress has an architectural drawing of the school in its collection.The building included clerestory windows for natural light.The school was demolished in November, 2012.Rudolph's oeuvre of work fell out of favor along with many works described as Brutalist architecture in the 1970s. But in the new millennium interest in his work, conservation, and restoration have brought renewed interest and vigor to preservation efforts seeking to maintain his remaining works.

SUNY Orange (Orange County Community College) is a public community college with two campuses, one in Middletown, New York and one in Newburgh, New York. It is part of the State University of New York (SUNY) system and offers almost 40 associate degrees and certificate programs. SUNY Orange is accredited by Middle States Commission on Higher Education. The college employs an open enrollment policy to all applicants who are graduates of an accredited high school or recipients of a state high school equivalency diploma.

The Paramount Theatre is a historic theater located at 17 South Street in Middletown, New York, United States. It was built in 1930 in an Art Deco style, a twin to the Paramount Theater in Peekskill, across the Hudson River. It was included in the National Register of Historic Places in 2002. Paramount-Publix Corporation (now Paramount Pictures) built and opened the building on June 12, 1930 with a celebration that included a parade at noon, a musical performance by the Paramount Symphony Orchestra, and the first movie, The Big Pond, starring Maurice Chevalier and Claudette Colbert at 6 p.m. The feature film was preceded by a newsreel, a short film about Middletown and its citizens and a welcome film starring Buddy Rogers.Paramount-Publix sold the theater after the U.S. Supreme Court's 1948 United States v. Paramount Pictures, Inc. decision, which required the movie studios to divest themselves of their theater chains. ABC, a successor corporation, owned the Paramount until 1973 when it sold it to Hallmark Releasing. After several other owners, it closed five years later. In 1979, the city took title when back taxes went unpaid.Two years later, the Arts Council of Orange County bought the building and renovated it into a performing arts center. An apron was added to the stage, and a pavilion on the back of the building provided dressing room space. It was reopened in 1985. The building was added to the National Register of Historic Places in 2002. The theatre hosts a variety acts and events, as well as art exhibits, lectures, civic fundraisers, dance recitals, business receptions, school theatre series, performing arts summer camp and some film features. The New York Theater Organ Society installed the Wurlitzer organ from the Clairidge Theater in Montclair, New Jersey. The Paramount's organ's original keyboard is now part of the organ at the Orpheum Theater in Phoenix, Arizona.

Middletown was the main station along the Erie Railroad mainline in the city of Middletown, New York. Located on Depot Street, the station was first opened in 1843 with the construction of the New York, Lake Erie and Western Railroad, which had originally terminated at Goshen. The station was located along the New York Division, which stretched from Pavonia Terminal in Jersey City, New Jersey, to the Sparrowbush station just north of Port Jervis. The building was opened in 1896 to replace one that had been in use since 1843 when the New York and Erie began service to the city. The Romanesque Revival building was designed by George E. Archer, Chief Architect of the New York, Lake Erie and Western Railroad, later the Erie Railroad. The station saw service for trains going from Chicago to Erie's terminal in Jersey City, and later, as part of Erie Lackawanna Railway, service to Hoboken Terminal. The last long distance train along this route was the Atlantic Express and Pacific Express in 1965. The station also saw regular commuter service. The building served as a railroad station until 1983, when rail service was taken over by MTA's Metro-North Railroad. Service on the route of Erie's original Main Line was discontinued in favor of the Graham Line, an Erie-built freight line now used by Norfolk Southern and the Port Jervis Line and was replaced by the Middletown Metro-North station. The station depot was renovated and restored, becoming the Thrall Library in 1995.

Grace Episcopal Church is a historic Episcopal church located at Middletown in Orange County, New York. The original church was built between 1846 and 1847, then enlarged and aggrandized in the Gothic Revival style between 1866 and 1868. A Collegiate Gothic style parish house was added in 1913. The church features an off-set bell tower with stepped buttresses and Gothic arched windows.It was listed on the National Register of Historic Places in 2010.

The Webb Horton House, is an ornate 40-room mansion in Middletown, New York, United States, designed by local architect Frank Lindsey. Built 1902-1906 as a private residence, since the late 1940s it has been part of the campus of SUNY Orange. This building is now known as Morrison Hall, after the last private owner, and houses the college's main administrative offices. A nearby service complex has also been kept and is used for classrooms and other college functions. The mansion is an extravagant combination of styles and materials that has been altered very little during its ownership and use by the college. In 1990 it was listed on the National Register of Historic Places.

The First Congregational Church of Middletown, New York, United States is one of the most visible landmarks of that city's downtown skyline. Its spire rises higher than any other church or structure in the central neighborhoods of the city. Constructed in 1872, this is the third church built by this congregation.The congregation was established in 1785, after the American Revolutionary War, by migrants who came from New England. The first church was built before residents had even named their settlement of houses and farms. It has been argued that the formation of the church at that time marks the beginning of Middletown's existence as a village. For 40 years it was the only church in the area. The current Gothic Revival building was designed by architect Isaac G. Perry and reflects the ambitions of the prosperous residents of the town of that period.

Middletown is the largest city in Orange County, New York, United States. 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. At the 2020 United States census, the city's population was 30,345, reflecting an increase of 2,259 from the 28,086 counted in the 2010 census. The zip code is 10940. Middletown falls within the Poughkeepsie–Newburgh–Middletown Metropolitan Statistical Area, which belongs to the larger New York–Newark–Bridgeport, NY-NJ-CT-PA Combined Statistical Area.Middletown was incorporated as a city in 1888. It grew in the 19th and early 20th centuries as a stop on several lower New York State railroads, attracting several small manufacturing businesses. The surrounding area is partly devoted to small dairy farms. Mediacom Communications Corp, the Galleria at Crystal Run, SUNY Orange, Walmart, Touro College of Osteopathic Medicine and the Times Herald-Record are major employers in Middletown.

Christ Church, more commonly known as the Unitarian Universalist Fellowship or First Universalist Church of Middletown is a historic Universalist church located at Middletown in Orange County, New York. It was built in 1901. It features an offset bell tower and Tiffany glass memorial window. Also located on the property is an earlier frame parish house.It was listed on the National Register of Historic Places in 2008.