The Town of Woodstock was originally settled in 1686 as New Roxbury by thirteen men (the Goers) from Roxbury, Massachusetts and became the first town in present day Windham County. Thirty families followed the Connecticut path west from Boston and settled in Wabbaquasset. The first homesteads were set up on Plaine Hill and the Westward Hill. Located on the conjunction of three Indian trails, the area was frequented by traders and was situated on the "great road from Hartford to Boston, and on the road from Providence to Albany." Woodstock has thrived since the early days and has played its part in history.  The Commons served as assembly sites for troops during the American Revolution, The War of 1812, and the Civil War. Roseland Cottage hosted Presidential visits in the nineteenth century. Please visit the Woodstock Historical Society Welcome Center next time you are in town and learn more about the fascinating history of our early New England town.