Mechanicstown, New York

Orange County Fair Speedway is a 0.625 mi (1.006 km) dirt oval speedway in Middletown, Orange County, New York. The facility holds weekly stock car races and demolition derbies during the summer months. The track was built in 1857 for horse racing at the Orange County Fair and staged its first automobile race on August 16, 1919. The fair began as an agricultural exhibit in 1843 and was permanently located in the Wallkill–Middletown area in 1857. The speedway is located at 239 Wisner Avenue in Middletown on land which was known as The Ogden Tract in the mid-1850s. It was originally a half-mile horse racing track known as the Harry Clay Oval, named after a race horse that was famous at that time. Over the years, the track was widened and lengthened to a true 5/8-mile race track.

Middletown High School serves 9th through 12th grade students in the Enlarged City School District of Middletown, which covers that city as well as adjacent portions of the towns of Wallkill and Wawayanda in Orange County, New York, United States. It is located on Gardner Avenue in a small outlying area of the city, near the county fairgrounds on a small rise south of NY 211. The school, formerly Anthony Veraldi Junior High School, built in 1959, replaced the building now known as Twin Towers Middle School as the district's high school in 1976 after a major expansion. It has been expanded at least four times since then.

Silver Lake is a small lake in Orange County, New York, located adjacent to New York State Route 17 exit 120 northeast of Middletown in Wallkill.

Washington Heights is a census-designated place (CDP) in Orange County, New York, United States. The population was 2,205 at the 2020 census. Washington Heights is a contiguous suburb of City of Middletown. The community is in the Town of Wallkill.

New York, Ontario & Western Railway Company Middletown Station, also known as the O&W Station, is an historic train station located at Middletown in Orange County, New York. It was designed by Bradford Lee Gilbert and built in 1892-1893 by the New York, Ontario and Western Railway. It is a three-story Richardsonian Romanesque-style pressed brick and sandstone building. It measures approximately 237 feet (72 m) long and has towers at the north and south end. Additions and alterations were made to the original building in 1904 and 1920, designed by Middletown architect David H. Canfield. Also on the property is the contributing two-story records storage building, built in 1915. The station closed on September 10, 1953, on the cessation of O&W passenger service. It was listed on the National Register of Historic Places in 2014, three years after the city, which owned it at the time, sold it for $1 to the Middletown Community Health Center (MCHC), which intended to redevelop it for its uses. But financial problems with the MCHC prevented it from raising the estimated $20 million cost of the project, despite winning some state grants. Those issues led to MCHC being bought-out by another health care organization; in 2017, it began negotiating to return it to the city. While Mayor Joe DeStefano says the city is open to offers, it is likely that the building will be demolished.

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.

Middletown–Town of Walkill station, often just referred to as the Middletown station, is a stop on the Metro-North Railroad's Port Jervis Line serving the city of Middletown and the town of Wallkill in Orange County, New York. The station is located in the latter municipality along the former Erie Railroad Graham Line. Two trains end at the station on weekdays, with one of them turning back for service to Hoboken. The station contains an elevated platform for access by passengers in wheelchairs, and expanded paid parking. In a switch from the other stations to receive these amenities, the platform roof at Middletown is green rather than red, platform light poles are brown instead of green and the wheelchair platform is not under the roof. While other Metro-North stations such as Cortlandt and Southeast are named after the towns in which they are located, the station is the only one to include "Town of ..." in its official name, to avoid longstanding confusion with the nearby hamlet in Ulster County. The station replaced the former Erie Railroad station on James Street in Middletown, which maintained service from May 26, 1843 to April 15, 1983. That building now serves as the Thrall Library. Middletown–Town of Walkill station opened on April 18, 1983.

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.

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.

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.

The Galleria at Crystal Run is a shopping center located in the Town of Wallkill, New York. It is the second-largest mall in New York's Hudson Valley region.