Bennington: First Town, First Republic, Fourteenth State


Bennington is Vermonts first town, chartered in 1749 by the colonial Governor of New Hampshire, Benning Wentworth, for whom the town was named. Bennington played a vital role in both the founding of the republic of Vermont and the Battle of Bennington in 1777. Bennington was also home to Ethan Allen and the birthplace of the Green Mountain Boys.

Vermont's constitution was the first on the American continent... a full decade before the U.S. constitution was written. It was also the first constitution to outlaw adult slavery. 

Today Bennington is a classic Vermont hometown. It has a population of between 15,000-16,000 and is the states sixth largest city. Close to metropolitan areas, the town has a historic downtown, hospital, and diverse economy with numerous annual events and festivals. Craft beer, a distillery, the Bennington Museum, the Battle Monument, hiking trails and three covered bridges await visitors.

First town
In 1749, Bennington was the first town chartered in Vermont by New Hampshire Governor Benning Wentworth. Actual settlement would take 12 more years. In the interim, a few tenant farmers working the land for their New York landlords, did live in the Pownal area. And a few families receiving title under the New York Patents, moved mostly into the Shaftsbury and Arlington area.

Puritan origins
On June 21, 1761, a group of 22 Congregational Separatists from Hardwick, Massachusetts arrived in Bennington to form a faith-based community, complete with a town government and schools. Led by Samuel Robinson, the settlers built a meeting house and called its first minister, the Rev. Jedidiah Dewey from Westfield, Massachusetts in 1763.

Robinson and Dewey were young men inspired by the Great Awakening led by Jonathan Edwards of Northampton, Massachusetts in the 1730s. Both Robinson and Dewey broke away from the Old Light congregations and formed New Light congregations in Hardwick and Westfield respectively. Robinson acquired the deeds to the lands originally created by Wentworth and sold them to his followers and other settlers from Massachusetts and Connecticut. Dewey led his faith community through the years of the Battle of Bennington.

God of the Hills
Conflicts between the settlers claiming title from New York and New Hampshire respectively led to the New Yorkers bringing ejectment proceedings in the New York courts in 1770. The settlers under the New Hampshire Grants engaged Ethan Allen to organize the defense of their titles. Allen hired an attorney from New Haven Connecticut. Not surprisingly, the New York Courts and prosecutors, who had apparent conflicts of interests, prevailed. Allen then formed the Green Mountain Boys, declaring “the Gods of the Valley are not the Gods of the Hills.” The Green Mountain Boys enforced New Hampshire grant claims and ejected those with competing grants from New York. Things came to a head in 1771 with the Stand-off at Breakenridge Farm on the Walloomsac River with the first armed confrontation between the New York colonial authorities and the settlers of what would become Vermont. While bloodless, the encounter showed that the grantees from New Hampshire were determined to enforce their claims. While violence was used during these years such as whippings and the burning of New York settler cabins, nobody was killed. The role of the Green Mountain Boys was soon to change from enforcement of land titles to an actual fighting force as the beginning of the Revolutionary War opened a new chapter in Vermont's story.

Capture of Ft. Ticonderoga
After the confrontations in Concord and Lexington in April of 1775, Ethan Allen organized a force of Green Mountain Boys to capture Ft. Ticonderoga on May 10, 1775. Support came from the political leaders in Connecticut. Benedict Arnold arrived on May 9 with word of support from the Massachusetts Bay Colony. 83 Green Mountain Boys crossed Lake Champlain before dawn and surprised the garrison, taking the fort without firing a shot. The cannons captured would be hauled across the Berkshires to Boston by a former bookseller, Colonel Henry Knox. The alignment of the cannon along Dorchester Heights led to the evacuation of Boston by the British on March 17, 1776.

The Boys join the Continental Army
Within months of the capture of Ft. Ticonderoga, the Continental Congress asked General Schuyler of New York to form a regiment of the Green Mountain Boys to serve in the Northern Department of the Continental Army. The Boys responded and served in the winter campaigns of 1775 and 1776 in Canada. In the spring of 1777, General John Burgoyne led a military expedition of about 7,500 men from Montreal down the Champlain Valley, headed for Albany, New York.

Burgoyne’s plan was to join up with forces under the leadership of General Howe coming up the Hudson River and General St. Leger coming from Lake Ontario. The combined forces would cut off the rebels in New England, dividing them from the other colonies. Howe decided to attack Philadelphia instead. St. Leger was turned back at Ft. Stanwix.

The Battle of Bennington
Progress was slowed by the terrain and local militia sympathetic to the rebels. Running short of supplies, Burgoyne sent Colonel Frederick Baum off toward Bennington where there was known to be a rebel storehouse. Cattle and horses, a key resource, were also said to be available. Rebel defenses were thought to be minimal. 

What General Burgoyne did not know was that Ira Allen had written to the New Hampshire government asking for help. And General John Stark had responded by raising a militia of 1400 men who marched to Manchester, where he met Seth Warner and the Green Mountain Boys. By August 9th, Stark and Warner had marched to Bennington, setting up campaign headquarters in the Catamount Tavern.

On the 14th, Stark’s men encountered Baum’s men a few miles northwest of town. Baum’s forces entrenched in place and sent for reinforcements. Stark’s forces withdrew and consolidated on a hillside a mile to the east. It rained on the 15th. The Battle of Bennington commenced on the 16th at 3:00. It lasted until dark.

The results were a total victory for Stark and the Green Mountain Boys. The British lost 907 soldiers at Bennington. It gave a huge morale boost to the rebels who had never before beaten a standing European Army in open battle. The troops confronting Burgoyne at Stillwater more than doubled in a month. And in two months, the numbers doubled again. Burgoyne surrendered his entire remaining forces at Saratoga, in what has been termed the turning point of the Revolution. Arguably, Bennington was the turning point of the turning point of the American Revolutionary War.

In spite of the importance of the Battle of Bennington and the continued participation in the Continental Army, efforts to join the Continental Congress were rejected. This led to a Declaration of Independence and a Constitution, establishing Vermont as an independent republic. The Republic continued until 1791, when Vermont was finally admitted to the union as the 14th State.

Industrial Revolution
As industry grew, activity began to shift downhill from the original village (now known as "Old Bennington") along the Walloomsac River which provided power to operate mills and machinery. Government offices and business soon followed, leaving Old Bennington behind as a quiet residential community.

The Bennington Trolley System
Until the 1890s, the only way to get around was to walk or use a horse.  Some enterprising folks would travel a route with a horse-drawn wagon and pick up travelers for a fee. Companies were formed to upgrade these routes and to make schedules more dependable.  Rails were laid along raised level beds to allow horses to pull heavier loads.  In 1898, the trolley took over these rail systems for shorter trips.  

The trolley motor was powered with current from an overhead uninsulated wire. Sparks flew and steel wheels screeched as the car ran along the rails. As the system grew, Bennington grew.  Workers from farther away could commute to work in the mills.  Shoppers along the rail lines could come to town, allowing businesses to flourish. The town could expand along these routes beyond easy walking distance.

For the next 29 years, the trolley extended its service.  The first route up to Woodford and the Glastonbury hotel and dance hall lasted only a couple years before it washed out in a flood and was never reopened. Routes to North Bennington and to Hoosick Falls were more sustainable.  The system connected to the Berkshire Trolley Line in June 1907, allowing travel to Williamstown, North Adams, Adams, Pittsfield, and all the way to Connecticut.  Parks were built along the way with concessions, ponds, and even swan boats. Up to 30,000 people rode these trolleys every day.

By 1918, automobiles were becoming more popular, Roads became smoother. Tires became softer, quieter, and more comfortable. Ridership on the trolleys decreased.  When the flood of 1927 washed out several sections of track, these were never repaired.  By 1930, the tracks and poles were all removed. Only the raised beds of the old trolley lines remain.

More information and resources:
Bennington Museum
Bennington250.org - Regional planning website for the 2025-2027 250th anniversaries