Woodstock is the shire town (county seat) of Windsor County, Vermont, United States. As of the 2020 census, the town population was 3,005. It includes the villages of Woodstock, South Woodstock, Taftsville, and West Woodstock.

Chartered by New Hampshire Governor Benning Wentworth on July 10, 1761, the town was a New Hampshire grant to David Page and 61 others. It was named after Woodstock in Oxfordshire, England, as a homage to both Blenheim Palace and its owner, George Spencer, 4th Duke of Marlborough. The town was first settled in 1768 by James Sanderson and his family. In 1776, Joab Hoisington built a gristmill, followed by a sawmill, on the south branch of the Ottauquechee River. The town was incorporated in 1837.

Although the Revolution slowed settlement, Woodstock developed rapidly once the war ended in 1783. The Vermont General Assembly met here in 1807 before moving the next year to the new capital at Montpelier. Waterfalls in the Ottauquechee River provided water power to operate mills. Factories made scythes and axes, carding machines, and woolens. There was a machine shop and gunsmith shop. Manufacturers also produced furniture, wooden wares, window sashes and blinds. Carriages, horse harnesses, saddles, luggage trunks and leather goods were also manufactured. By 1859, the population was 3,041. The Woodstock Railroad opened to White River Junction on September 29, 1875, carrying freight and tourists. The Woodstock Inn opened in 1892.

The Industrial Revolution helped the town grow prosperous. The economy is now largely driven by tourism. 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 cost of real estate in the district adjoining the Green is among the highest in the state. 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.

The town maintains a free (paid for through taxation) community wi-fi internet service that covers most of the village of Woodstock, dubbed “Wireless Woodstock”.

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 author goes on to explicate some of the informal rules, such as that buildings stand close to the sidewalk, in the case of businesses, or ten to fourteen feet behind for homes; that plots are generally deep and narrow, keeping street frontages roughly equivalent; commercial buildings stand side by side, with only important buildings with a public function—the library or courthouse, for instance—being free-standing objects. 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.