Chester Today

The village of Chester is located in southern end of a region known as the “Heart of Vermont.” New York, Boston, and Hartford are all within a comfortable driving distance, yet we are far enough North to get a good snowfall for all wintertime activities.

Life in Chester centers around the Village Green. The Chester House Inn is located on the North side of the Green. Also located on and near the Green are restaurants, a country store, art galleries, clothing shops, gift shops, book stores, a teddy bear shop, a quilt shop, a cafe, a leather shop and the Chester Historical Society.

In the summer and fall, activities on the green include craft fairs, art shows, children playing and bicyclists resting aching muscles after a long bike ride. Of course you can sit in a rocker on our front porch and watch village life pass by on any day. And on Memorial Day and on Alumni Day (in June), you’ll have a front row seat for the parade.

The Chester of Yesterday

In 1764 the original charter was granted by New Hampshire to the town of Flamstead. The first town meeting was held in 1765 after which a 1766 New York State charter claimed the town, now renamed “Chester.”

One of the first colonial Declarations of Independence was adopted at a Chester town meeting on November 10, 1774 – twenty months before the Continental Congress in Philadelphia. Vermonters fought in the Revolution, insisting on Statehood of their own rather than becoming part of New Hampshire or New York. We remained an independent republic until 1789.

Many stagecoach inns were operated in Chester, with a stage line from Boston to Montreal intersecting here with a line from Hanover to Albany. In 1849, the railroad from Boston to Lake Champlain was completed and Chester became a commercial and shipping hub.

Chester is located at the convergence of three branches of the Williams River and offered fertile soil for farming to the early settlers. Farming, transportation and industry brought prosperity to Chester which helped build the many Colonial and Victorian homes along main street. Early in the 20th century, industry moved East, but Chester nonetheless retains to this day the elegance and charm of a Colonial New England village in the rural countryside.