2011 Great Places in America: Streets-Downtown Woodstock Streetscape, Woodstock, Vermont. Downtown Woodstock's four principal streets bring together scenic mountain skylines, early 19th century New England architecture, and 250 years of history. Elm Street has some of the oldest properties in Woodstock including the Dana House and F.H. Gillingham & Sons general store. The Green, Woodstock's community front yard is the location of the weekly farmers market.