VT 23, maintained locally its entire length rather than by the state of Vermont, runs northwest past some homes as a two-lane road on the western side of Middlebury.

Paralleling the Otter Creek, leaving downtown Middlebury near a junction with Pulp Mill Bridge Road.

[5] Now in the rural sections of Weybridge again, VT 23 makes a gradual curve to the southwest near the junction with Drake Road, the route returns to a parallel with the Otter Creek.

Continuing along the creek, the route and the waterway make a big turn to the north, crossing through rural Addison County.

VT 23 turns away from the creek for a short distance, returning to sides at Thompson Hill Road.