Previous to the disputes of boundaries with New York and New Hampshire, North Bennington was held under a title known as Walloomskoick, patent by Joseph Haviland.  In 1739 he built a grist mill on Paren Creek and ground grain for General Stark and his troops. 

In January of 1749 New Hampshire Governor Benning Wentworth chartered Bennington, the first town grant in Vermont.

Bennington was the first settlement in Vermont, west of the Green Mountains.  In June, 1761, the first settlers, about twenty people, came from Massachusetts.  About thirty to forty more arrived later that year, including Samuel Robinson and Joseph Safford.  Safford Street carries his name.  By the end of four years, fifteen hundred people settled on the “Hill”, now known as Old Bennington.

Each household was self sufficient, providing their own food, clothing and shelter.  They ground their corn by hand and built their houses with hand hewn logs.  A grist mill to grind the grain and a saw mill to produce lumber would make life much, much easier.

On March 31, 1762, a town meeting was held.  The attendees voted to give fire acres of land and forty dollars to anyone  who would built a grist mill, no later than August first of that same year.  Also, at the same meeting, a like sum was offered to build a saw mill on the east side of Bennington and a similar one of the west side, now known as Bennington Falls or Papermill Village, no later than September first.  The Walloomsac River has the greatest water power at Papermill Village.  Samuel Robinson and Joseph Safford built a grist mill (the first grist mill in Vermont) on the east side of the Walloomsac River, the present location of the junction of Beech and Main Streets, and a saw mill on the west side of the river, which is the present junction of Main and Morgan Streets.  They built a dam, later called Benton Pond.  Safford Mills continued into the 1800’s.  Their fee for services, grinding grain at the grist mill was three quarts of grain for every bushel processed.  Safford Mills was the first of many mills to be constructed on the Walloomsac River.

Prior to 1800, the valley, East Village, had two roads, North and South Streets and Main Street from Bennington Centre (Old Bennington) to Safford Mills.  East of Safford Mills was wilderness.  In 1804, East Main Street was extended to Furnace Grove, which is just west of the Bennington/Woodford Town Line.

In 1800 there were no more than twenty houses in what later became the Village of Bennington.  Early in the 1800’s the valley began to increase in population and prosperity.  Water wheels were needed to operate the blast furnaces.  In 1785, Eldad Dewey built a gristmill and dam creating Dewey Pond, later known as Depot Pond.  At this same time, Captain John Norton settled in Bennington and purcshasesd a farm south of town,  He built the first pottery kiln.  The clay was dug on the property, or from near by, to make the Redware pottery.  Production continued until 1984.

George Keith built the first forge, to make cut nails, near the present Benmont Street bridge, which operated into the 1800’s

In 1811, there was a foundry on North Street.  Later, the site was sold to Henry W. Putnam and became a grist mill. 

Furnace Brook had several blast furnaces.  One was in the Lyons District, built by Moses Sage from Sage City, now the Village of North Bennington, built about 1800.

Between 1810 and 1820, there appeared a blacksmith shop on Maine Street, along with a tannery and distillery.

Bennington had three public schools in 1765.  Later, the Union Academy was constructed on the site in front of the Village Cemetery on Main Steet.  Prior to 1870 there were five district schools in Bennington.  A town meeting held in April 1870, voted to consolidate and build one centrally located school.  The new school opened on School Street in 1875.

In the very early years of Bennington, after the settlers had cleared and cultivated the land, built comfortable dwellings and out souses, built roads and bridges, demonstrating a thriving and prosperous community, the Kind of England and his agents took a hard look at the Benning Wentworth Charter, thinking that this land and territory belonged to others, other than the folks that were in residence.  As a result of this fuss, the Green Mountain Boys were formed to protect the rights of citizens of the town and they established their headquarters in Bennington at the Catamount Tavern.  This gave the town some early importance.

In 1777, Bennington had a large store of supplies that the English felt they should come to Bennington and remove, to satisfy their own needs.  General stark and the Green Mountain Boys successfully fought off the English, keeping the stores in Bennington.

To commemorate this victory the Bennington Battle Monument was erected, and dedicated by President Benjamin Harrison in 1891.