Picturesque village

Chester, Vermont 2020

Chester is a large city located in the southern part of Windsor County in the US state of Vermont. The Williams River runs through the city and serves as a retreat for anglers, children, and everyone else, aiming to cool off on hot summer days. The city is located on the hills of the Green Mountains which offer fun summer and winter activities. Incredibly picturesque, Chester is popular with tourists, especially in the summer, with its historic Stone Village and historic Chester Village neighborhood.

Geography and climate of Chester

Aerial view of fall colors in Chester, Vermont.

Chester covers a total area of ​​144.9 km², of which only 0.7 km² is covered by water and 144.2 km² is covered by land. The city is surrounded by Baltimore to the north, Springfield to the east, Grafton to the south and Weston to the west, minutes from Okemo Mountain and Mount Snow and just 45 minutes from Manchester.

Chester’s climate is humid continental, with hot, humid summers and freezing, snowy winters, with cloudy skies all year round. The temperature generally varies between -12°C and 26°C and is hardly lower than -21°C nor higher than 30°C. For tourists, the best time to visit Chester for warm weather recreation is between June and September.

Brief History of Chester

The Chester Depot Station Depot, Chester, Vermont
The Chester Depot Station Depot, Chester, Vermont. Editorial Credit: Bob LoCicero /

In 1754, the town was originally incorporated as Flamstead by New Hampshire Governor Benning Wentworth. Charter standards were not met and the town was renamed New Flamstead in 1761. Later, in 1766, a license was issued by New York to rename the town Chester after George Augustus Frederick – the Earl of Chester and the eldest son of King George III. Subsequently, Chester’s governmental authority reverted to the 1761 charter by an act of the Vermont Legislature, despite retaining the name “Chester” in place.

Chester’s population and economy

Christmas decorations adorn an inn in Chester, Vermont
Christmas decorations adorn an inn in Chester, Vermont. Editorial credit: James Kirkikis /

According to the last US census, Chester has a population of 3,005. 90.32% of these residents were born in the United States, with 51.22% being born in Vermont. The town has no immigrants and all residents are US citizens. Chester’s economy relies on manufacturing and retail as a strong sector in its structure, followed by construction and healthcare services. From another perspective, the average annual income of a Chester resident is $33,293, subject to 6.0% sales tax and 6.8% income tax.

Top Attractions in Chester

Stone Village Historic District

The Stone House bed and breakfast in the Stone Village in North Chester, Vermont
The Stone House bed and breakfast in the Stone Village in North Chester, Vermont. Editorial Credit: Bob LoCicero /

The Stone Village Historic District is home to a special collection of stone buildings dating back to the 19th century. The district is dotted with a remarkable collection of buildings constructed using a particular technique of cut stone brought to the region by Scottish masons. The neighborhood was listed on the National Register of Historic Places in 1974. Due to the rarity of this building style in the United States, the neighborhood attracts many visitors eager to explore the buildings, including homes, a school, a church, and some commercial buildings.

Okemo State Forest

Okemo State Forest covers 7,466 acres in Andover, Mount Holly and Weston, and in Vermont in Windsor and Rutland counties. Okemo Mountain Resort is located in the forest operated by the Vermont Department of Forests, Parks and Recreation. The forest hosts activities such as hiking, biking, skiing and hunting. Parts of the forest allow primitive camping. Additionally, the Okemo State Forest is home to the 798-acre Terrible Mountain Natural Area.

Located near the Green Mountains, Chester was the main hub of commercial activity in southern Vermont in the 19th century. Fortunately, many historic buildings, including Yosemite’s fire station and Chester Depot train station, have survived. Charming Victorian houses, decorated with domes and iconic stone houses, are well preserved with care and can be found all around the streets of the town. While many things have developed in the city, other backbones of local culture remain, such as maple sugaring season, which welcomes spring in a tasty way.