During the winter of 1776, in one of the most incredible logistical feats of the Revolutionary War, Henry Knox and his teamsters transported cannons from Fort Ticonderoga through the sparsely populated Berkshires to Boston to help drive British forces from the city. This history documents Knox's precise route--dubbed the Henry Knox Trail--and chronicles the evolution of an ordinary Indian path into a fur corridor, a settlement trail, and eventually a war road. In the process, it reveals the deeper story of the colonial fur trade, Indian raids, early settlers, taverns, militia movements during the French and Indian Wars, and General Jeffery Amherst's Pioneers, who widened the forest path for their march into New York colony in 1758, and for Knox's reverse trip nearly two decades later. By recounting the growth of this important but under appreciated thoroughfare, this study offers critical insight into a vital Revolutionary supply route.