Windsor-5 Vermont Representative District, 2002–2012

Windsor County is a county located in the U.S. state of Vermont. As of the 2020 census, the population was 57,753. The shire town (county seat) is the town of Woodstock. The county's largest municipality is the town of Hartford.

Top Acres Farm, known historically as the Fletcher–Fullerton Farm, is a farm property at 1390 Fletcher Schoolhouse Road in Woodstock, Vermont. Developed as a farm in the early 19th century, it was in continuous agricultural use by just two families for nearly two centuries. It was listed on the National Register of Historic Places in 2004.

Jenne Farm is a farm located in Reading, Vermont, United States. It is one of the most photographed farms in the world, especially in autumn. The farm has appeared in magazine covers, photography books and several Budweiser television advertisements; it has also served as a setting in the films Forrest Gump and Funny Farm. Photographs of the farm have appeared on posters, postcards and wall calendars.Despite its fame, the private farm is located along a dirt road and is not heavily promoted. The only sign indicating its presence is a tiny board along Vermont Route 106 advertising maple syrup.The farm became noted for photogenic scenery around 1955, when a photography school in South Woodstock discovered it. Later, it appeared as an entry in a Life photography contest, on the cover of Yankee magazine and in Vermont Life.As a result of being overrun by tourists trespassing on the farm, the town has closed the road leading to the farm to non-local traffic.

The Owen Moon Farm is a historic country estate on Morgan Hill Road in South Woodstock, Vermont. Set on a steeply sloped 8-acre (3.2 ha) parcel are its main house, an 1816 brick building, a barn, and a 1930s bungaloid guest house. The hilly terrain is heavily landscaped, forming an important visual component of the estate, and serving to afford it privacy from the nearby public roads. It was listed on the National Register of Historic Places in 1983, primarily for the well-preserved Federal period architecture of the main house.

The Woodstock Warren Through Truss Bridge was a historic iron bridge that carried Bridges Road (Town Highway 24) across the Ottauquechee River in western Woodstock, Vermont. The bridge was built in 1925, and was a rare example of the state of a double-intersection Warren through truss. The bridge was swept away by flooding caused by Hurricane Irene in 2011; it was listed on the National Register of Historic Places in 1992.

The Lincoln Covered Bridge is a historic covered bridge, just south of U.S. Route 4 in West Woodstock, Vermont. Built in 1877, it is one of the only known examples of a wooden Pratt truss bridge in the United States. It was listed on the National Register of Historic Places in 1973.

The Bridgewater Woolen Mill, now more commonly the Bridgewater Mill Mall, is a historic textile mill complex on United States Route 4 in Bridgewater and Woodstock, Vermont. With an textile processing history dating from 1828 to 1975, it was one of the state's longest-lived textile operations, and was a mainstay of the local economy during that period. It has since been repurposed into a shopping center. It was listed on the National Register of Historic Places in 1976.

South Woodstock is an unincorporated village and census-designated place (CDP) in the town of Woodstock in Windsor County, Vermont, United States. Its elevation is 1,040 feet (320 m), and it is located at 43°33′56″N 72°31′56″W (43.5656256, -72.5323158), in the Kedron Valley.A post office was established in South Woodstock in 1828; today, its ZIP code is 05071. The ZCTA for ZIP Code 05071 had a population of 456 at the 2000 census. The ZCTA includes large areas outside the village district and includes the entire southern portion of the town of Woodstock. Once a center of sheep husbandry, South Woodstock is split between commercial and residential areas. Beside the post office, public services in the community include a volunteer fire department; moreover, Woodstock maintains a local police department.The South Woodstock Village Historic District was listed on the National Register of Historic Places in 1983. The historic district consists of 44 contributing and 11 non-contributing properties over an area of 360 acres (150 ha), including a significant concentration of brick buildings. The district includes examples of Greek Revival and Federal architecture from before the American Civil War. Notable buildings include an 1825 school that became a Grange Hall, the South Chapel (1839), and the Perkins Academy (1848).

Reading is a town in Windsor County, Vermont, United States. The population was 687 at the 2020 census.

The Wales N. Johnson House is a historic house at 43 Senior Lane in Woodstock, Vermont. Built in 1889-90 by the owner of a local sawmill, it is a high quality example of vernacular Queen Anne architecture. Now serving as the Jackson House Inn, it was listed on the National Register of Historic Places in 1995.

Saddlebow Farm is a historic farm property at 2477 Gold Coast Road in Bridgewater, Vermont. With a history dating to the 1780s, the property is a fine example of the conversion of agricultural properties to summer and tourist-oriented uses in the 20th century. The 140-acre (57 ha) property was listed on the National Register of Historic Places in 2002.

Woodstock Union High School (WUHS) is a mid-sized public secondary school located in Woodstock, Vermont, United States. As a member of the Windsor Central Unified Union School District, the school serves seven towns: Barnard, Bridgewater, Killington, Plymouth, Pomfret, Reading, and Woodstock. In addition, WUHS receives tuition students from other surrounding towns such as Hartland, Ludlow, Pittsfield, Sharon, Stockbridge, and Weathersfield, among others. The institution is accredited by the New England Association of Schools and Colleges. Woodstock serves approximately 385 High School students and 190 Middle School students.