Geographically, the town of Bennington is the largest in Wyoming County, occupying a significant portion of the county's northwest corner.
The Town of Bennington was formed in 1818 from part of the Town of Sheldon. The Town of Bennington officially came into existence on March 6, 1818. The name came from Bennington Vermont.
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"In 1802, the land of Bennington was part of the Town of Batavia, Genesee County. The in 1808, the land was taken from the Town of Batavia, to form the Town of Sheldon. Finally, on March 6, 1818, the land of Bennington was taken from Sheldon to form the Town of Bennington.
In the summer of 1802, John Tolles settled in Bennington. He settled in the area known over the years as Hubbard's Corners, Danley's Corners and the "Beehive".
The first frame barn was erected in the township by Jacob Wright in 1805.
By 1806, over twenty families were located in the town. A tannery, shoe shop and blacksmith shop were erected. By 1807, the first school house was built. A sawmill was also built in the south part of the town near the Sheldon Town line. In 1806, Chauncey Loomis purchased large tracts of land in the third and fourth ranges of the township at the price of one dollar per acre, including all the land now known as Bennington Center. During 1807, a sawmill was built in Bennington Center and the first barn raised was built from lumber produced from the mill. Also in 1807, the road from Bennington to Sheldon was cut out.
Approximately nine years after the Loomis family settled in Bennington, Quartus Clapp set out to purchase his own land further west in the town. He selected a site four miles down Cayuga Creek near a waterfall and built a sawmill in 1816 or 1818. He purchased about a hundred acres, which covered more than half of the valley of the hamlet of Cowlesville. At that time it was known as Clapp's Mills.
During 1826, Quartus Clapp built a grist mill adjoining his saw mill. This grist mill was the first of its kind in this town.
In 1827, Gaius B. Rich came from Attica and established the first store in Clapp's Mills. A young man, Hiram Cowles, clerked in this store in 1831. It was at this store that mail came once a week for the local settlers to pick up. It is believed that Hiram Cowles had a great deal to do in establishing the Post Office at Clapp's Mills, for on March 11, 1831, he was appointed Postmaster. In his honor, the settlement received the name of Cowles villes.
The hamlet of Folsomdale is three miles southwest of Bennington Center. John Fitch came to Folsomdale, built a house, set out an orchard and built a saw and grist mill, about 1823. Little is known about Fitch but his property was purchased in 1825 by David Scott. He began a mercantile and milling business in this area.
When David Scott owned the land Folsomdale is located on, the name of Scottsville was given to it. About 1831, Benjamin Folsom came to Scottsville to manage a store for Mr. Scott. In 1834-1835, Mr. Scott built a tavern. It was later owned and operated by Mr. Folsom and it was after that, the hamlet was named Folsomdale.
The first Bennington town meeting was held in home of David Farnham. The first supervisor, for the town, was George Loomis.
On January 23, 1875, a meeting was held in Cowlesville with the purpose of dividing the Township into two towns. A resolution was drawn up and presented to the Board of Supervisors. The board, with a vote of ten to five, approved the resolution to create a new town on February 25, 1875. The new township was to be "Elmont". When the request was sent to the Legislature of New York State, there was some error in proceedings and the proposal died in Albany.
Until the 1930s, town meetings were probably held in the schoolhouse at Bennington Center. In 1936, during Franklin D. Roosevelt's presidency, the Works Progress Administration, known as W.P.A., provided jobs in building projects for a long-range value. The Town of Bennington had their town hall built. The federal government furnished the cost of labor for the building. The building is still used for the Town meetings. Several other organizations also use it.
Bennington was mainly a farming community. The 1990 Wyoming County Dairy Princess was from the Town of Bennington.
The Town had several small schools. The last school to close its doors was District #17, located in Cowlesville.
The town of Bennington boasted of six covered bridges to span the Cayuga Creek. The last of the six, known as the Ellis-Chesbro covered bridge, was destroyed by fire on March 17, 1966. It was the last structure of its kind that existed in New York State west of the Finger Lakes. At one time, the Ellis-Chesbro Bridge was the location of scenes shot for MGM's motion picture "The Great Waltz".
Francis Folsom, the granddaughter of John B. Folsom, became the First Lady of the United States. She spent much time as a young girl in Folsomdale. Frances Folsom was married to President Grover Cleveland, June 2, 1886 at the White House in Washington, D.C.
The Town of Bennington has had several churches. The first Baptist Church in Bennington Center was erected in 1832, the second in 1857 and that was destroyed by fire in 1886. It was rebuilt in 1887. BY 1925, the membership had diminished to five. The church was sold to the Cowlesville Baptist Society. They dismantled it and rebuilt it as an addition to their church.
The United Church of Christ in Bennington Center was dedicated in 1844. The Sacred Heart Catholic Church was erected at Bennington Center in 1871. The East Bennington Evangelic and United Brethren Church dates back to the early 19th century. The Catholic Church, Our Lady Help of Christians, in East Bennington was built in 1855. The Cowlesville Baptist Church was built in 1872 and an addition was added in 1924 or 1925. Cowlesville also had a Universalist Church which was dedicated in 1845. In 1914, the building was sold to the I.O.O.F. Lodge. It was eventually dismantled. The German Baptist Church was erected in 1869 at Folsomdale. There also was a Free Will Baptist Church in Folsomdale dedicated in 1858. The building was torn down in the early 20th century.