It was named after Woodstock in Oxfordshire, England, as a homage to both Blenheim Palace and its owner, George Spencer, 4th Duke of Marlborough.

[7] The Woodstock Railroad opened to White River Junction on September 29, 1875, carrying freight and tourists.

Woodstock has the 20th highest per-capita income of Vermont towns as reported by the United States Census, and a high percentage of homes owned by non-residents.

The town's central square, called the Green, is bordered by restored late Georgian, Federal Style, and Greek Revival houses.

The seasonal presence of wealthy second-home owners from cities such as Boston and New York has contributed to the town's economic vitality and livelihood, while at the same time diminished its accessibility to native Vermonters.

[10] In his City Life: Urban Expectations in a New World, Canadian author and architect Witold Rybczynski extensively analyzes the layout of the town and the informal and unwritten rules which determined it.

According to Rybczynski: The overall plan seems to have been dictated by the site: a narrow, flat valley hemmed in by the sweeping curve of the Ottauqueechee River on one side and a small creek on the other.

The green was laid out lengthwise on the narrow peninsula between the river and the creek, allowing for many plots to have rear gardens running down to the riverbank.

The pride of place, on the green, is shared by private homes on one side, and the courthouse and the Eagle Hotel on the other.

If Parisian planning in the grand manner can be likened to carefully scored symphonic music, the New England town is like ... very restrained jazz.

Rybczynsk points out that there is no zoning in Woodstock, and "buildings with different functions sat—and still sit today—side by side on the same streets", with practical exceptions such as the slaughterhouse and the gasworks.

[citation needed] In the late 1960s they tore down the landmark Woodstock Inn, a Victorian treasure reconstructed in 1892 from the old Eagle Hotel, which served as a center point for the town, and built a charming neo-colonial edifice farther back from the street.

[13] Woodstock was named "The Prettiest Small Town in America" by the Ladies Home Journal magazine,[14] and in 2011, North and South Park Street and one block of Elm Street won an award for great streetscape by the American Planning Association's "Great Places in America" program.

It is bordered by the town of Pomfret to the north, Hartford to the northeast, Hartland to the east, Reading to the south, and Bridgewater to the west.

Vermont Translines operates a daily intercity bus route between Rutland and Lebanon, stopping in Woodstock along the way.

[25][26] F. H. Gillingham & Sons, a general store located in its original building at 16 Elm Street, is another local tourist attraction.

The park preserves the site where Frederick Billings established a managed forest and a progressive dairy farm.