Windsor-1-1 Vermont Representative District, 2002–2012

Chester is a town in Windsor County, Vermont, United States. The population was 3,005 at the 2020 census.

The Williams River is a 27.0-mile (43.5 km) river in the US state of Vermont. It is a tributary of the Connecticut River. Its watershed covers 117 square miles; land use is about 80% forested and 4% agricultural, and the upper river supports wild brook trout and brown trout. The river was named for John Williams of Deerfield, Massachusetts. He preached the first Christian sermon in what would become Vermont near the mouth of the river on March 5, 1704. His text was from Lamentations 1:18: "Hear now, all peoples, And behold my sorrow; My virgins and my young men Have gone into captivity." A historical marker was placed near the site of the sermon in 1912 (see photo). At the time, he and part of his congregation were captives of the French, the Mohawk and the Abenaki after the Deerfield Raid, being marched from Deerfield, MA to Quebec, Canada.The Williams River rises in the northern part of the town of Andover and flows east through a corner of Ludlow and into Chester, where it turns southeast. The river then flows in a narrow valley near Vermont Route 103 between rolling hills into the town of Rockingham, where it joins the Connecticut River at Herricks Cove. Its major tributaries (from upriver to downriver) include Wheaton Brook, Lovejoy Brook, and Bear Brook in Andover and Ludlow. In Chester, it is joined by the Middle Branch Williams River, which starts in Windham; the tributaries of the Middle Branch include Lyman Brook, Andover Branch, and South Branch Williams River. Named tributaries in Rockingham include Wright Brook, Stearns Brook, Wiley Hill Brook, and Divoll Brook (flowing north), and Skunk Hollow Brook, Petty Brook, Brockways Mills Brook, Lillie Brook, Locke Brook, and O'Brien Brook (flowing south). The lower part of Petty Brook (in Bartonsville) was the mainstem of the river until a flood in 1869 changed its course. The Williams River watershed lies south of the Black River watershed, which includes most of Springfield, and north of the Saxtons River watershed. In Rockingham it is crossed by the Bartonsville Covered Bridge that was washed away in Hurricane Irene in August 2011, rebuilt in 2012, and reopened in January 2013, as well as the Worrall Covered Bridge, the only 19th century covered bridge left in town. Below those bridges, it flows over Sokoki Falls, named for the local band of the Abenaki, and through Brockways Mills Gorge. The river is a target for prospectors who can be seen panning for placer gold, south of the Town of Ludlow, near the site of the Rio Tinto open-pit talc mine.

The Jeffrey House is a historic house on North Street in Chester, Vermont. Built in 1797, it is one of Vermont's small number of surviving Georgian style houses. It was built by the son of one of the area's early settlers, and originally served as a tavern. It was listed on the National Register of Historic Places in 1974.

The Chester Village Historic District encompasses the historic southern portion of the main village of Chester, Vermont, US. Essentially a linear stretch of Main Street (Vermont Route 11), this area includes some of the village's oldest (late 18th century) buildings and has an architectural history spanning into the early 20th century. The district was listed on the National Register of Historic Places in 1985.

The Stone Village Historic District encompasses a distinctive collection of stone buildings on Vermont Route 103 in Chester, Vermont. Dating to the first half of the 19th century are a remarkable concentration of buildings constructed in a regionally distinctive snecked ashlar technique brought to the area by Scottish masons. The district was listed on the National Register of Historic Places in 1974.

Proctor Piper State Forest covers 1,513 acres (6.12 km2) in Cavendish, Vermont in Windsor County. The forest is managed by the Vermont Department of Forests, Parks, and Recreation. Activities in the forest include hunting and snowmobiling.

Chester is a census-designated place (CDP) in Windsor County, Vermont, United States. The population was 1,005 at the 2010 census. The CDP is a statistical area encompassing three distinct places: the urbanized center of the town of Chester; a locale known as Chester Depot, which is separated from the town center by the tracks of the former Rutland Railroad; and the village of North Chester. For many years, the Steamtown rail collection ran train excursions on these tracks between Chester Depot and Bellows Falls before relocating to Pennsylvania. Today, Vermont Rail System operates freight trains along the line, and the depot is still visited by passengers riding the Green Mountain Flyer, also operated by VTR. Chester Depot is known for the Stone Village, a street with several stone houses built in similar style. Stone was an uncommon building material in rural Vermont.

The Fire District No. 2 Firehouse, also known locally as the Yosemite Engine House, is a historic fire station at 716 Depot Street in Chester, Vermont. Built in 1879, it is architecturally distinctive in the state as the only period fire station with two towers, which also distinctively exhibit Second Empire styling. Now owned by the town, it was listed on the National Register of Historic Places in 2020.

The Augustus and Laura Blaisdell House is a historic house at 517 Depot Street in Chester, Vermont. Built in 1868 for a local businessman, it is a fine local example of transitional Greek Revival-Italianate architecture. It has historically served both commercial and residential functions, and now contains apartments. It was listed on the National Register of Historic Places in 2014.

Williams River State Forest covers 108 acres (0.44 km2) in Chester in Windham County, Vermont. The forest is managed by the Vermont Department of Forests, Parks, and Recreation.Activities in the forest include hiking, snowshoeing, hunting and wildlife viewing. The south branch of Williams River (Vermont) flows along the edge of the forest.

Andover is a town in Windsor County, Vermont, United States. The population was 568 at the 2020 census.

The Greenwood House, now the Gingerbread Apartments, is a historic house on Vermont Route 103 in Chester, Vermont. Built about 1850 and restyled about 1900, it is an architecturally distinctive blend of Greek Revival and Late Victorian styles. It was listed on the National Register of Historic Places in 1985.