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.

VT 253 turns north on the bridge's right-of-way, passing some homes before reaching the Beecher Falls–East Hereford Border Crossing.