VT 253 begins at an intersection with VT 114 (Gale Street) and VT 102 in the town of Canaan near the New Hampshire state line. VT 253 is a northern continuation of VT 102, which also ends at the intersection with VT 114. VT 253 runs north along Christian Hill, passing the local cemetery near Kingsley Road. The route, a two-lane residential road, leaves downtown Canaan, passing a dam on the Connecticut River, which parallels VT 253. When nearby Power House Road merges in, VT 253 runs alongside the river, crossing a former railroad grade, which parallels along the northern side of the highway. Winding along the riverside across from US 3 in New Hampshire, the route turns away in short spurts from the railroad grade, passing some homes.[3]
In the northern section of Canaan, VT 253 turns eastward along the river and enters Beecher Falls, reaching a four-way junction with a bridge over the Connecticut River. The bridge connects VT 253 and US 3. VT 253 turns north on the bridge's right-of-way, passing some homes before reaching the Beecher Falls–East Hereford Border Crossing. North of the border crossing, VT 253 runs north for a short distance, reaching the Quebec provincial line, where it continues north as Route 253.[3]