One of Vermont's most scenic and well-preserved villages, Grafton was founded in 1763 and soon grew into a thriving settlement. By 1850, the town was home to a population of 10,000 -- er, 10,000 sheep, that is. It also boasted a hotel that provided shelter for guests on the stagecoach road between Boston and Montreal. A cheese cooperative was organized in 1890, and a soapstone industry flourished for a time. But as the agriculture and commerce shifted west and to the bigger cities, Grafton became a shadow of a town -- by the Depression, many of the buildings here were derelict.
Then something remarkable happened. In 1963, Hall and Dean Mathey of New Jersey created the Windham Foundation. A wealthy relative who had recently died entrusted the two brothers to come up with a worthy cause for her fortune; it took a few years, but they eventually hit on Grafton, where their family had summered. The Matheys began purchasing and restoring the dilapidated center of town, including the old hotel. This foundation eventually came to own some 55 buildings and 2,000 acres around town -- even the cheese cooperative was revived. The village sprung back to life, and it's now teeming with history buffs, antique hounds, and tourists instead of farmers and merchants. The Windham Foundation has taken great care in preserving this gem of a village, even to the point of burying utility lines so as not to mar the village's landscape with wires.
To the north, Chester is less pristine and more lived-in: There are actual grocers, diners, and gas stations here. Yet the downtown area has a pleasant, neighborly feel and some attractive old architecture; you can also find a handful of boutiques and shops along the main road. Chester is a great stop for antiquing, too, with several good dealers in the area. If you're heading north of town along Route 103, be sure to go slowly through the Stone Village, a neighborhood of well-spaced, austere stone homes lining the roadway. Many of these are rumored to have been safe havens on the famous Underground Railroad once upon a time.