Running northeast past Bishop Donnelly Park, the route passes the nearby middle school and enters a rural section of the town of Torrington.

Now a triplex through Winchester, the routes make up the four lane South Main Street, passing through downtown.

After a fork with nearby Spencer Street, Route 183 and US 44 condense down to two lanes and leave downtown Winchester.

A two-lane rural area outside of Winchester, Coe Street soon becomes Colebrook Road and meanders to the northwest on a far-distance parallel with US 44.

Entering the town of Colebrook, Route 183 reaches a junction with Millbrook Road, where it turns northeast.