Woodstock

Right off the bat, Woodstock looks different from most of the quaint villages in southern Vermont [1]. 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 [2] and Connecticut [3]. In 1793, Captain Israel Richardson built a tavern on the town green to serve the traffic from the stagecoach that passed through from Boston [4] to Canada. That site is now occupied by the Woodstock Inn [5], 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 [6]. Woodstock is also a good place to get in touch with Vermont’s [1] agricultural side, with a farm museum and cheese-maker [7] in town.