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.