VT 8 begins at the Massachusetts state line in the town of Stamford. The highway continues south as Route 8 toward North Adams. 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. VT 8 and VT 100 enter the town of Readsboro just before reaching the source of the river. The highways curve east to the headwaters of the West Branch of the Deerfield River at Heartwellville. There, VT 100 continues southeast along that river. VT 8 turns north along an unnamed tributary of the river, which the highway follows to its source at the Readsboro–Searsburg town line. The highway continues north to the town center of Searsburg, where it reaches its northern terminus at VT 9 (Molly Stark Highway) between Bennington to the west and Brattleboro to the east.