The Hamlets of Woodstock

A hamlet is defined as “a small settlement, generally one smaller than a village.” In Woodstock, there are five hamlets as well as the Village of Woodstock. The hamlets are: Prosper, West Woodstock, South Woodstock, Taftsville, and Willow Vale.

Hamlets were usually centered around a mill or some other type of industry, and they often had their own stores, churches, grange halls, and meeting houses.

The following provides a brief overview of each of Woodstock’s hamlets as well as the Village of Woodstock.

Prosper, formerly named English’s Mills, was so named because of the prosperous nature of that community. The mill was located at the junction of Austin Road and Rt. 12 on Prosper Brook, sometimes called Barnard Brook. Mr. English employed a large mill crew, the Prosper school educated its children, and farmers along Barnard Brook did well. It was a stop on the way to Barnard, on the Woodstock-Royalton turnpike. There has always been a unique community spirit in the area known as Prosper.

West Woodstock had at one point had its own store, school and post office. It was anchored by Daniels Machine Company, a large manufacturing facility which sat adjacent to the site of the current Woodstock Farmer’s Market. There was a dam here on the river, and a mill pond to generate water power for the factory. There has also been many bridges spanning the river at this location. This area was an important road intersection that connected multiple Woodstock neighborhoods and communities.

A part of West Woodstock was referred to as “The Flats” before being renamed. The renaming of this hamlet was quite controversial at the time as people stated that they were firmly in the center of the town, and the only thing they were west of was the Village.  It was suggested that the bustling hamlet be named Centerville, which never happened.

South Woodstock, once called the South Parish or South Village, has its main section listed as a National Register Historic District. This hamlet has always felt like a separate town with its own schools, academy, stores, tavern, hotels and manufacturing mills along the Kedron Brook. It continues to maintain its own post office today. Farming on Fletcher Hill and Long Hill, especially during the sheep boom, was very successful.

Taftsville, also listed as a National Register Historic District, was anchored by the large iron manufacturing facility on the river, operated by the Taft Family. There were also mills on Happy Valley Brook, a brick yard, stores, a church, and - in the late 1800s - a railway station. The valley straddling Happy Valley Brook also has a successful farming community.

Taftsville is named for the first settler of the village, Stephen Taft, who arrived from Massachusetts around 1793, although there seems to have been some agricultural enterprises in the vicinity earlier. He soon built a power dam on the Ottauquechee River, and a factory on the south riverbank to make axes, scythes, and other edge tools necessary in this period of expanding agriculture. His brother Daniel Taft arrived as an apprentice in 1794 and later set up his own business. Meanwhile, Stephen Taft built a sawmill on the north riverbank. Later came a plow and stove factory, a gristmill, a shingle mill, a chair factory, a brickyard, a blacksmith shop, a tannery, and a slaughterhouse.

Willow Vale is situated about one mile north of the Village, and its entrance was about where the Pomfret and Barnard roads meet at what has been called “Thompson’s garage.” The area extended out towards South Pomfret along the Pomfret Road and also along Rt. 12 towards Prosper. The “Vale” has always contained many beautiful meadow farms and fine residences. At one time it was noted for its fine flocks of Merino sheep and later dairy operations. Its inhabitants were described as “enterprising, hard-working people, noted for their industry and frugality.” The name of the Vale derives from the shrubbery that dominated the Barnard Brook. Over the years, the identity of Willow Vale has merged with Prosper, and there are only a few locals living in this area who remember the previous name.

Village of Woodstock, listed as a National Register Historic District, was organized on the first Monday in January 1837 and provided for the election of five trustees as the governing board of the village. Originally, this section of town was called the North Village or “the Green.” It began in 1772 with the family of Joab Hoisington and grew to about 1,500 in the mid-1880s. The original limits of this portion of town were laid out in 1819 in an effort “to restrain certain animals from running at large within the villages of this State.” Over a century and a half, the village has become firmly established as the commercial, economic and political hub of the town.

Prosper Homemakers’ Meeting

View of West Woodstock

Historically known as The Flats

Kedron Tavern &

Holt’s Cash Store

South Woodstock

The Center of Taftsville

A view of the bridge, mills, railroad depot, houses and other buildings.

The County Courthouse in the village, built in 1855.