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Founded in 1802, it was probably named for its location about midway between Dayton (approximately 20 miles [32 km] north) and Cincinnati.
A post office was established October 22, 1816, with Stacy Beakes as postmaster.
In 1821, Middletown purchased its first piece of fire-fighting equipment known as the “Bread Tray,” because of its resemblance to one.
Wallkill Academy, a private school and Middletown’s first institution of higher learning, was opened in 1842.
The Middletown Association was formed and raised the money to lay the track to Middletown, the first train reaching here May 26, 1843.
Orange County Furnace, a foundry and manufacturer of metal products, opened 1843 on Center Street.
Middletown remained terminus of the line until the road opened to Otisville November 1, 1846.
Middletown was incorporated as a village in 1848 with Stacy Beakes as the first village president.
63. (9) David D. Field, D.D. Centennial Address, with Historical Sketches of Cromwell, Portland, Chatham, Middle-Haddam, Middletown and its Parishes (Middletown, Conn.: William B. Casey, 1853) pg.
Matthews & Hunt began the manufacture of carpet bags and other products in 1853 in the building long occupied by Ayres & Galloway Hardware at the corner of North and Roberts Streets.
When the Wallkill Guards left Middletown on May 3, 1861, they were presented with a silk flag by the ladies of the village.
He sold the business to the Howell-Hinchman Co. in 1866 who enlarged the operation considerably.
The Middletown & Crawford, running from Middletown to Pine Bush, was opened in late 1871.
Another significant event in Middletown’s history was the opening of the State Homeopathic Hospital for the Insane, later known as Middletown Psychiatric Center, in 1874.
(1) Henry Whittemore, History of Middlesex County: The Town & City of Middletown (New York, N.Y.: Beers Co., 1884) pg.
Middletown was incorporated as a city June 29, 1888, with John E. Iseman as the last village president and first mayor.
Thrall Hospital opened May 10, 1892 at 21-23 Grove Street.
The new station opened in 1897.
George M. Verity built a mill (1900) that produced sheet steel by the continuous rolling process.
Thrall Library on Orchard Street opened in January of 1901 on the site of the old Orchard Street School.
The hospital closed when Horton Hospital opened in 1929.
Radio station WALL began broadcasting from Middletown August 2, 1942.
Fancher-Davidge Park at the end of Lake Avenue was formally dedicated by the city on July 4, 1943.
Orange County Community College opened 1950 in the former mansion of Webb Horton on South Street.
The city began buying and demolishing properties in 1958 with the program continuing a number of years.
In 1978, the New York State Department of Transportation announced plans to upgrade the rail line from Port Jervis through Orange County.
Middletown later became the site of a large railroad yard and shop facilities for the line which was abandoned in 1957. It was later purchased by the Erie, inherited by Conrail, and abandoned in 1978.
48. (14) R.W. Bacon "More insights from Hannah McKinney's research: 'Who Counts in the Community?'" The Middler, Fall 2006 (Newburyport, Mass.: Society of Middletown First Settlers Descendants, 2006) pg.
A new facility was built on East Main Street in the Town of Wallkill and the hospital on Prospect Avenue closed in 2011.
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