Most of present-day Middletown is located in what was a large tract of land known as the Minisink Angle which was surveyed, divided into lots, and eventually sold to settlers. Middletown was settled between about 1760 and 1770 by the Green, Moore, Wickham, Everett, and Wells families who settled along East Main Street and Highland Avenue. Stacy Beakes (the elder) settled in the vicinity of Eisenhower Drive in 1771. East and West Main Streets were once part of the old Minisink Road which ran east through Mechanicstown and Phillipsburg and on to Goshen, and west through Mount Hope. The oldest house in Middletown is believed to be the Nathaniel and Jerusha Wickham Wells house at 315 East Main Street built 1775. At the time of its settlement, Middletown was in Ulster County with the Orange County line just to the south. In his will, John Green left land to build a church and the First Congregational Church was built 1786 on the site of the present structure on East Main Street. A graveyard was established on the grounds as well.
Precisely when and why the locality was named Middletown is uncertain, although there are a number of theories. One idea is that it was about halfway between the Hudson and Delaware Rivers. Another is that it was between other settlements, and one historian suggests it may have been named after Middletown, Connecticut. A more recent idea involves the settlement's location in a line of signal fires used during the Revolutionary War, giving a new significance to why Beacon Street was so named.
A private school was established 1791 on the site of 15 South Street next to the Paramount Theatre. The boundary line between Orange and Ulster Counties was changed in 1798 to its present location and Middletown became part of Orange County. Middletown was also part of the Town of Wallkill which was formed from the old Wallkill Precinct. The first library was established here in 1801 and a tannery about 1805. The tannery, considered Middletown's first industry, would eventually move and erect the large factory buildings on Fulton Street between Wawayanda Avenue and Mulberry Street. In 1809, the Montgomery Turnpike was chartered running through Middletown to Montgomery, and, in 1810, Dr. David Hanford became the hamlet's first physician.
During the War of 1812, the local militia company known as the Wallkill Republican Blues under the command of Stacy Beakes served briefly in 1813, mostly doing guard duty. Also in 1813 a public school was established, meeting in the former private school on South Street, moving to a new building on the corner of North and Depot Streets in 1818. A post office was established October 22, 1816, with Stacy Beakes as postmaster. This was kept in his store on the north corner of West Main and North Streets. The post office itself, a wooden cabinet with compartments for mail, survives and may be seen at the Historical Society at 25 East Avenue. From June 23, 1829, to September 10, 1849, the name of the post office was known as South Middletown to avoid confusion with another Middletown, now known as Middlehope, just north of Newburgh.
In 1821, Middletown purchased its first piece of fire-fighting equipment known as the "Bread Tray," because of its resemblance to one. The first brick structure, a house that stood at 37 South Street, was built 1836 to 1837. The first brick business block was built for Lewis Vail and still stands at 2 West Main Street. This was built about 1837 or 1838. The hamlet's first bank was chartered in 1839 and the first newspaper published in 1841 although it didn't last long. Wallkill Academy, a private school and Middletown's first institution of higher learning, was opened in 1842. Torn down 1896, the Academy's bell survives and may be seen at Thrall Library. The Academy stood where the present Academy Avenue School stands on the corner of Little Avenue.
Orange County Furnace, a foundry and manufacturer of metal products, opened 1843 on Center Street. Founded by Elisha Pearl Wheeler and others, the company soon became an important industry in Middletown. After the initial settlement and establishment of the First Congregational Church, the most significant event in the history of Middletown was the arrival of the New York and Erie Railroad in 1843. The road reached Goshen in 1841 and could proceed no further due to lack of funds. The Middletown Association was formed and raised the money to lay the track to Middletown, the first train reaching here May 26, 1843. Middletown remained terminus of the line until the road opened to Otisville November 1, 1846. From 1838 to 1848 Middletown's population more than tripled.
Middletown was incorporated as a village in 1848 with Stacy Beakes as the first village president. The Whig Press, Middletown's first true local newspaper, was first published by Jonathan Hasbrouck November 26, 1851. Matthews and Hunt began the manufacture of carpet bags and other products in 1853 in the building long occupied by Ayres and Galloway Hardware at the corner of North and Roberts Streets. Another business started the same year would soon become a significant contributor to Middletown's prosperity. Wheeler, Madden and Bakewell, saw makers, would eventually be owned by the Clemson family with products distributed world-wide. The modern fire department was organized in 1859, the original companies being Excelsior, Eagle, and Phoenix.
Many from Middletown volunteered to serve in the Civil War as members of the Wallkill Guards, the Tenth Legion, and the Orange Blossoms, among others. When the Wallkill Guards left Middletown on May 3, 1861, they were presented with a silk flag by the ladies of the village. When they returned in June of 1863, they returned the battle-scarred flag. The flag was eventually placed in the Middletown Library then on North Street, moved to Thrall Library Building when it opened on Orchard Street, and finally to the Historical Society in 1941 where it remains on display. Three Middletown Civil War Veterans received the Congressional Medal of Honor and are buried in Hillside Cemetery, these being Sgt. Thomas D. Collins, Pvt. Nathan M. Hallock, and Capt. Lewis S Wisner. Capt. Wisner's great-great-grandfather served in the Second Continental Congress and was present when the Lee-Adams resolution for independence was passed July 2, 1776. The "Declaration of Independence" was not signed by Mr. Wisner as he returned home to manufacture gun powder in nearby Phillipsburg.
After the Civil War, several railroads were built through Middletown. The first of these, the Middletown, Unionville, and Water Gap was completed in December 1867, and operates today as the Middletown and New Jersey. The New York and Oswego Midland, which later became the New York, Ontario and Western (O&W), was completed in 1873, with Middletown's Elisha P. Wheeler driving the ceremonial last spike. Middletown later became the site of a large railroad yard and shop facilities for the line which was abandoned in 1957. The Middletown and Crawford, running from Middletown to Pine Bush, was opened in late 1871. It was later purchased by the Erie, inherited by Conrail, and abandoned in 1978. An attempt by Middletown and New Jersey to purchase the line was not successful and the rails were ripped up.
In 1863, operation of the tannery was moved from Canal Street to Fulton Street by Lewis Moore. He sold the business to the Howell-Hinchman Co. in 1866 who enlarged the operation considerably. The building was further expanded after it was acquired by the Horton family. Operations ended about 1937. The large factory building at 9-29 Canal Street some still refer to as the Borden's Building began as a much smaller structure erected by the Orange County Milk Association in 1869. This was sold to the Anglo-Swiss Condensed Milk Co. (Nestles) in 1882 who much enlarged the plant, and to Borden's in 1902 who made their own additions to the building.
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. The three original buildings for patients were the Main Building, completed in 1874, Pavilion I opened in 1876, and Pavilion II completed in 1881. The Main Building and Pavilion I were demolished in 1980 while the abandoned Pavilion II was damaged by fire in 2015 and torn down. The psychiatric center closed in 2006, although a small number of patients are cared for in the Schmitz Building operated by Rockland Psychiatric Center. Several buildings at the former psychiatric center have been converted to other purposes and remain in use.
Telephone service began in 1881. Middletown was incorporated as a city June 29, 1888, with John E Iseman as the last village president and first mayor. The event was celebrated on Independence Day with fireworks and other festivities at Academy Avenue Park. This had been the site of two cemeteries which had been converted to a park in the mid-1880s. Electric lights were first used in Middletown in 1889. The power plant was located at 164-168 West Main Street. Thrall Hospital opened May 10, 1892 at 21-23 Grove Street. Dr. Julia E Bradner was behind the efforts to establish a hospital and Mrs. S Maretta Thrall donated the land and funding to build the hospital. The hospital closed when Horton Hospital opened in 1929. Mrs. Thrall also gave the land to the city that became Thrall Park, completed in 1894 and named in her honor.
The original armory building on Highland Avenue on the corner of John Street, was completed in 1892. Two large additions were made to the structure, the first completed in 1901 and the other in 1903. Trolley service in Middletown began in 1894, not only serving the city, but running to Midway Park on the Wallkill River across from the golf club and on to Goshen. Service was discontinued in 1924. In 1896, the Erie demolished the original depot and began construction of the present building now part of Middletown Thrall Library. The new station opened in 1897. Tuthill Cut Glass Company was established in 1899, closing in 1923. Thrall Library on Orchard Street opened in January of 1901 on the site of the old Orchard Street School. Mrs. Thrall had left funds in her will to build the library.
Calbraith Perry Rogers made aviation history in 1911 when he became the first person to cross the United States by plane. He left Long Island September 7, 1911, landing here later that day. It was estimated about 12,000 people saw the landing. Taking off the next morning, he brushed a tree and crashed into a chicken coop in the rear of a house on what is now Sterling Street. Mr. Rogers was not badly injured, but his plane, the "Vin Fiz" was damaged and he didn't leave Middletown until September 21st. He finally reached the Pacific Ocean in California December 10, 1911.
City Hall on James Street was completed in December of 1911. The Elizabeth A. Horton Memorial Hospital on Prospect Avenue opened March 12, 1929, and Central Fire House on East Main Street was completed in May of the same year replacing a smaller truck house that had been built in 1873. The Paramount Theatre on South Street opened June 12, 1930. The Paramount closed in 1978 but the badly deteriorated building was purchased and restored by the Arts Council of Orange County and reopened in 1985. 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. The park originally opened as Columbia Park, which was privately owned, in 1894. Orange County Community College opened 1950 in the former mansion of Webb Horton on South Street. This magnificent home was built 1901 to 1907, designed by Middletown architect Frank J. Lindsey.
In 1955, the Common Council began discussion of an Urban Renewal Program. This involved acquisition of properties within a certain area, demolition of existing structures, and redevelopment of the property. The city began buying and demolishing properties in 1958 with the program continuing a number of years. Housing on Fulton Street was torn down and the land used for other purposes. The buildings on the east side of James Street were torn down and the present James Street parking lot created. There were many other changes as well, but these were among the most significant. While many problems were addressed, the city planners also made some poor decisions such as the destruction of buildings of historical importance and the senseless elimination of commercial structures that should have remained on the tax rolls.
When the original Orange Plaza opened on Route 211 in 1972, most of Middletown's long-time retailers eventually moved from downtown or closed. In 1978, the New York State Department of Transportation announced plans to upgrade the rail line from Port Jervis through Orange County. A choice had to made between the old Erie main line through Middletown, or the newer Graham line which went around the city. As in the past, Middletown campaigned for the elimination of the railroad through town which, it was hoped, would allow redevelopment of the former railroad land. When the rail line through Middletown was abandoned in 1983, it did not bring about the changes planners predicted.
One positive aspect was the building of a new library which included restoration of the former Erie station at James and Depot Streets. The new Middletown Thrall Library opened February 12, 1995. Horton Hospital merged with Arden Hill Hospital of Goshen in 2002 and became Orange Regional Medical Center. A new facility was built on East Main Street in the Town of Wallkill and the hospital on Prospect Avenue closed in 2011. Three years later, however, in 2014 Touro College of Osteopathic Medicine opened in the former hospital building, graduating its first class of physicians in 2018.
Although Middletown suffered when most of the downtown shopping district closed down, the city has seen old store and factory buildings redeveloped and reopened. For example, a number of restaurants have opened downtown, and Middletown is now home to two breweries. The abandoned Crawford furniture store on King Street was converted to housing and has the motor vehicle office on the ground floor. The Babco*ck and Fuller hat works at Mill and Harding Streets, built 1873 and abandoned for years, was converted to housing and opened in 2016. Buildings formerly used for patient care at the Middletown Psychiatric Center have been repurposed and are in use.
Those interested in learning more about Middletown's history are invited to stop by the Historical Society of Middletown and the Wallkill Precinct at 25 East Avenue open Wednesdays from 1 to 4 pm.
Peter Laskaris,
Middletown City Historian
