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.

During 1826, Quartus Clapp built a grist mill adjoining his sawmill.

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.

When David Scott owned the land Folsomdale is located on, the name of Scottsville was given to it.

The first Bennington town meeting was held in home of David Farnham.

On January 23, 1875, a meeting was held in Cowlesville with the purpose of dividing the Township into two towns.

The board, with a vote of ten to five, approved the resolution to create a new town on February 25, 1875.

When the request was sent to the Legislature of New York State, there was some error in proceedings and the proposal died in Albany.

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 boasted of six covered bridges to span the Cayuga Creek.

It was the last structure of its kind that existed in New York State west of the Finger Lakes.

The Ellis-Chesbro Bridge was the location of scenes shot for MGM's motion picture "The Great Waltz".

Frances Folsom was married to President Grover Cleveland, June 2, 1886, at the White House in Washington, D.C.

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.

New York State Route 77 and NYS 354 (Clinton Street) pass through the town.

New York State Route 98 crosses the southeastern corner of the town.

As of the 2000 United States Census[5] there were 3,349 people, 1,208 households, and 966 families in the town.