Settled shortly before the Revolution, Middletown grew dramatically after the Erie railroad arrived here in 1843. Industries grew and retail stores were concentrated on North Street, James Street, and East and West Main Streets. Further growth occurred with the opening of the State Hospital in the 1870s and the establishment of extensive railroad facilities for the New York, Ontario, and Western Railway.
Although there have been many changes over the years, a large number of Victorian and early twentieth-century homes and buildings remain, including factories and commercial structures. A walk through Middletown's downtown reveals many interesting store buildings. On South Street is the Paramount Theatre which opened in 1930 and was built by the Elias Nielsen Construction Company of Middletown. It was designed by well-known theatre architect George L. Rapp (1878 to 1941) of Chicago. Many fine homes are located along Highland Avenue, the oldest of which dates to about 1838. Middletown is also known for its many fine churches, several of which are downtown. Middletown is also home to Hillside Cemetery at the end of Mulberry Street which was designed by Calvert Vaux, the same architect who designed Central Park in New York City.
Here is a brief mention of some the interesting structures that may be found in Middletown:
- Webb Horton Mansion, 115 South Street: Built 1901 to 1907 at a reported cost of one-million dollars for industrialist Webb Horton (1826 to 1908), the home features magnificent craftsmanship and a large Tiffany Studios stained-glass window. It was designed by Middletown architect Frank J. Lindsey (1854 to 1930) and built by Mitchell and Stever of Binghamton. The architectural style has been described as Queen Anne/Chateauesque. In 1950, the former Horton estate became the site of Orange County Community College.
- Webb Horton Memorial Presbyterian Church, 50-58 East Main Street: Erected by Eugene Horton to honor the memory of his father, this church was built on the site of an older church which was demolished in 1912. The present building was dedicated in 1914. Built by the Miller-Reed Co., the church was designed in the Romanesque style by Thomas Hastings (1860 to 1929) of the firm Carrere and Hastings. They were probably best known for designing the famous New York Public Library building on Fifth Avenue in New York City. Carrere and Hastings were among the leading architects of New York City, second only to McKim, Mead, and White.
- Clemson Brothers Saw Works, 22 Cottage Street: The saw business in Middletown was started by Elisha P. Wheeler and Edward M. Madden in 1853 on the corner of Center and King Streets with saw maker Josiah J. Bakewell. The business grew and a large factory was built in 1856 on the corner of Railroad Avenue and Cottage Street. Mr. Bakewell was succeeded by William Clemson in 1860 who gained control of the company after the deaths of Mr. Wheeler and Mr. Madden. In 1879, his son George N Clemson (1854 to 1930) who once lived in a mansion where the YMCA is on Highland Avenue, formed a partnership with his brother Richard W Clemson (1858 to 1923). In 1889, they began construction of an attractive factory building on Cottage Street which was completed in early 1890. The architect was John A. Remer of New York City, the masons were Malone and Hadden of Middletown, and the carpenter was Peter F. Miller, also of Middletown.
- Hiland H. Hunt house, 26 Courtland Street: Mr. Hunt (1818 to 1902) was a partner in the Matthews and Hunt carpet bag factory which was located on the corner of North and Roberts Streets in the building long occupied by Ayres and Galloway Hardware. The factory was an early contributor to Middletown's economic prosperity. Mr. Hunt's house was completed in 1857 and was designed in the Italian Villa style by architect Gervase Wheeler (born about 1824, died 1889). The house is important because of Mr. Hunt, but also because of its architect. Mr. Wheeler was a contributor to the books by Andrew Jackson Downing of Newburgh who was one of America's most influential architects. Mr. Wheeler also wrote two books of his own and was an early developer of the Stick-style of architecture which helped give rise to the Queen Anne style. Mr. Wheeler also designed Middletown's original firehouses located on King Street (torn down) and John Street (greatly altered), and the Exchange Building at 44-46 North Street which was demolished in 1968.
- Central Fire House, 81 East Main Street: An earlier two-bay firehouse on the site was demolished in 1928 to build the present structure completed in 1929. The Excelsior and Eagle Companies moved to the new house from the old King Street fire station joining the Monhagens and McQuoids. The building was designed by Middletown architect Robert R. Graham (1891 to 1943) in a Colonial Revival style and built by Middletown contractor Neilson Kinnear (born about 1884, died 1957). Despite some additions, the station retains an attractive appearance.
- William T. Hulse house, 113 West Main Street: This house was built in 1883 for Mr. Hulse who ran a furniture store with J. R. Van Duzer. Born 1842, he died at his home in 1887. Designed by Middletown architect Cornelius J. Sloat (1834 to 1898), it was built by Middletown contractor William W Carpenter (1836 to 1905). While so many homes have been ruined by vinyl or aluminum siding and other alterations, this house maintains a fine original appearance.
- Former Middletown High School, 112 Grand Avenue: Called "Twin Towers" for many years, the former high school opened in 1940 and was built as a Public Works Administration project. The building was designed by Robert R. Graham who also designed Central Fire House. Mr. Graham, who was well-known and respected as a school architect, described his design as "Modern Gothic."
- John Morris Cash house, 59-61 Wickham Avenue: John Morris Cash (1802 to 1846) purchased land from the Wickham estate in 1842 and built a house about the same time. The Greek Revival-styled house was built by John Kirby Moore (1811 to 1900) who was an architect and builder. The house at 34 East Avenue, also in the Greek Revival style, was another house built by Mr. Moore. The Cash House was placed on the National Register of Historic Places in 2017.
- Iseman Building, 44-46 James Street: A number of Victorian-era store buildings in Middletown have remained much as they were when originally built. One fine example of this is the Iseman Building on James Street built in 1889 for John E Iseman. Mr. Iseman (1835 to 1921), a baker by trade, has the distinction of being the last village president and first mayor of Middletown in 1888. Peter F. Miller (1835 to 1919) was the contractor and the building was probably designed by Cornelius J. Sloat (1834 to 1898) who served as an alderman and designed a number of buildings in downtown Middletown.
- Edwin Welling Van Duzer Memorial Home, 25 East Avenue: Another well-preserved example of Victorian architecture, this nice Queen Anne-styled house was built for Mr. Van Duzer (1860 to 1916) in 1887 as a gift from his father J. R. Van Duzer, a Middletown furniture dealer. The house was constructed by the Lindsey Brothers and designed by Frank J. Lindsey. In 1939, Harriett Decker Van Duzer, Edwin's widow, donated the house to the Historical Society of Middletown and the Wallkill Precinct, Inc. who continue to operate the house as a museum and research center.
This represents just a small selection of some of the fine homes and buildings in the City of Middletown. Whether walking through the downtown business district or in residential areas, there are many interesting structures to be seen.