VT 8 connects the southeastern Bennington County towns of Stamford, Readsboro, and Searsburg.

The state line is also the southern terminus of VT 100; the two routes head north along two-lane Main Road parallel to the North Branch of the Hoosic River through the town center of Stamford.

The highways curve east to the headwaters of the West Branch of the Deerfield River at Heartwellville.

VT 8 turns north along an unnamed tributary of the river, which the highway follows to its source at the Readsboro–Searsburg town line.

Much of Route 8 follows the course of the 1920s era New England Interstate Route 8, a part of the New England road marking system that ran from Bridgeport, Connecticut, through Pittsfield, Massachusetts, to Wilmington, Vermont.