In 1802, the land of Bennington was part of the Town of Batavia, Genesee County.  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 schoolhouse 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. 

     In 1808, the land was taken from the Town of Batavia, to officially form the Town of Sheldon.  Finally, on March 6, 1818, the land of Bennington was taken from Sheldon to form the Town of Bennington. 
     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 Cowlesville. 
     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 1930's, town meetings were held in the Macabee Hall 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, with several small businesses located throughout the town.  Today, farming continues, as well as several business, although most residents work outside of the town boundaries in Buffalo, Batavia, Attica and other nearby communities.

The Town had several small schools. The last school to close its doors was District #17, located in Cowlesville. 
 

Covered Bridges

The town of Bennington boasted of six covered bridges, five to span the Cayuga Creek and one located in Bennington Center, during the late 1800's and into the 1900's.. 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".  On June 1, 2022 a newly constructed covered bridge was opened on Schoellkopf Road.  This was at the site of a previous covered bridge - the Mosier Bridge.  That bridge had been removed in the early 1900's and replaced with an iron bridge which served residents until 2022.    The new bridge was dedicated on June 9, 2022 and named the Cannon Covered Bridge in honor of Sgt. Charles Cannon, killed in action in World War II.
 

Famous Residents

Francis Folsom, the grand-daughter 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 1990 Wyoming County Dairy Princess was from the Town of Bennington. 

​

Churches

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 1800's. 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 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 1900's.

​

​

Bennington Historical Society

The Town of Bennington Historical Society was created in the 1970's as part of the American Bicentennial celebration.  In those early years, members renovated the former Cowlesville Library building, located at 211 Clinton Street, into the new Town Historical Museum and began collecting local artifacts for the museum's display.  In the years that followed, several hundred donations and purchases have been made to fill the museum with a look at Bennington's history through the 19th, 20th and 21st centuries.  The museum grounds include flower beds, a gazebo, a memorial walkway (bricks available to purchase) and several artifacts, including the original grist stones from Quartus Clapp's mill.  The grounds were dedicated as Memorial Park during the 1975 Bicentennial, and are the site of several seasonal events, including a summer concert and Society fundraisers such as a hot dog sale and strawberry shortcake social

​

Bennington Historical Museum hours of operation are:

• Third Sunday of the month, April through November from 1pm - 3pm.

• Tours can be arranged by appointment.

• The museum is also open from 10AM - 4pm during the Cowlesville Flea Market (the second Sunday in July each year).

​

The Bennington Historical Society can be contacted by phone at 585-813-1082.  2023 Officers are President Edith Grant, Vice President Edward Spencer, Treasurer June Spencer and Secretary Ellen Grant.  The Society meets monthly on the fourth Tuesday from April to November, at 7 p.m.  Special programs and presentations are held throughout the year, either at the museum or Town Hall, and are posted at the Town Hall and the Message Board at the Museum.