Right off the bat, Woodstock looks different from most of the quaint villages in southern Vermont . The scale is grander, the houses more stately, and the downtown buildings more self-important. That’s partly because shortly after the town was founded in 1765, it became the shire town for the county surrounding it, drawing a professional class of lawyers, doctors, teachers, and businesspeople who brought wealth and culture with them.
Today, Woodstock embodies both country-cute and upscale refinement, with an unparalleled village green surrounded by Victorian homes and a collection of upscale shops and galleries.
Almost from its beginnings the town has been a favorite tourist destination with visitors from Massachusetts  and Connecticut . In 1793, Captain Israel Richardson built a tavern on the town green to serve the traffic from the stagecoach that passed through from Boston  to Canada. That site is now occupied by the Woodstock Inn , which was founded in the 19th century to serve the growing tourist traffic from the railroad.
In 1934, the first rope tow was installed on a pasture at the north end of Woodstock, ushering in a new era of winter sports for the moneyed set. That area survives as the modest ski area Suicide Six . Woodstock is also a good place to get in touch with Vermont’s  agricultural side, with a farm museum and cheese-maker  in town.