North of Killingworth center, it intersects with Route 81, about 1.9 miles (3.1 km) west of the Chester line.

Upon entering Chester, the road becomes West Main Street, continuing eastward toward the town center.

In Chester Center, the road becomes Water Street, which continues to an intersection with Route 154 (for Deep River and Haddam).

This series of turnpikes was envisioned by its proponents as part of an all-turnpike route between New Haven and Norwich.

The business proved unprofitable, however, and between the years of 1842 and 1847, the various turnpike companies along the Route 148 alignment were dissolved and the roads turned over to the towns.