Located around the confluence of three branches of the Williams River, the area that is now Chester, Vermont offered fertile farmland to eighteenth century settlers.

What we now call Chester was chartered in 1761 by the Governor of New Hampshire, under the name "New Flamstead." The first wave of farmers arrived in 1764, and in 1766 the town's name was changed to Chester. The town of Chester was forward thinking and adopted its own Declaration of Independence in November 1774 -- twenty months before the Continental Congress in Philadelphia. Vermonters fought unexpectedly well during the American Revolution. The Green Mountain Boys caused General Johhny Burgoynne's Hessian expedition under Lt. Col. Baum, sent to pacify the area and recruit Tories, to virtually disappear from the face of the earth during the battle of Bennington. At Bennington, the British lost 200 dead and 700 captured in the battle compared to only 70 total American casualties.  The total victory over the British force was a very impressive achievement and dealt a significant blow to Burgoyne's army.  At Saratoga, the British only had about 4,400 left, so Bennington helped make the surrender at Saratoga possible. Bennington was the first indication that Burgoyne was in deep trouble, and his surrender two months later made American independence possible. A small group of Vermonters set the stage for one of the turning points in human history.

Having caught the spirit of independence, Vermonters  demanded statehood of their own.  At the time the area was a territorial dispute between New Hampshire or New York. Vermonter's settled the dispute by declaring then maintaining an independent republic until 1789. That republic's constitution is still in effect and is the oldest such constitution in the world.

One thing that sets Chester apart from other places is the "Stone Village".  The Stone Village consists of 10 buildings, including a church, former schoolhouse, and several private residences. Built in the 1830's and 1840's by itinerant masons with stone from the nearby hills, these buildings are beautiful example of 'snecked ashlar' or glimmer stone masonry. Ten out of the original ten stone buildings originally built on North Street is still occupied and in beautiful condition.

In the middle of the nineteenth century the railroad linking Boston and Burlington came to town, and Chester became a transportation hub for surrounding area. As in other areas the railroad brought with it  a new prosperity, which is still evident. All you have to do is walk or drive through town and you will see many fine examples of various styles of Victorian homes. These late-19th century homes and buildings on Main Street are now part of a historic district in the National Register of Historic Places, while the older stone houses along North Street comprise a unique "Stone Village."

It was at this time that the town set up the Town Farm on what is now Vt. Rte. 10 on the edge of the township, midway between Chester, Ludlow, and Springfield. In the nineteenth and well into the twentieth century, the Town Farm served many different functions. It was a working farm that offered property owners in economic hard times an alternative way to pay their air share of the town's tax burden. Itinerant or migrant people could always find work, bed and board at the far. And the farm served as an alternative to incarceration for petty offenders. Today, the Old Town Farm Inn is sadly no longer a working farm, the bulk of the land having been sold off by short sighted former owners.

By the beginning of the twentieth century, the industrial revolution had taken over most of the north eastern United States. As the century progressed, local factories and shops worked around the clock and night to meet wartime demands. Yet even through wartime economic booms and economic depressions, Chester managed to retained the elegance and charm of Victorian village and rural countryside. This ambiance today draws visitors from around the world.

Perhaps what separates Vermont in general, and Chester in particular from the rest of the country is that we have kept a sense of community. Chester is more than where we reside, it is where we live. Our schools are excellent with tremendous community involvement and support.  Missing in town are the strip malls and general sprawl that afflict most of the country. People know one another here, talk to one another and friendships here span generations. 

Yes we have it pretty good here by any standards. Which is why Chester's people are almost always smilingo active.