In the 1920s, state highway 316 followed the pre-freeway Route 8 between Shelton and Bridgeport. Route 8 existed at the time, but followed present-day Route 110 to Stratford. This section of road became Route 65 in 1932.

The modern Route 316 was commissioned in 1963, from former SR 816, which might date back to 1932.

Where's that confounded bridge

In the 1970s, Route 316 narrowed to a single-lane railroad underpass a short distance south of US 6. After the railroad was abandoned, the state removed the bridge, widened Route 316 to two lanes, and relocated the northern end. Monument Lane is the old alignment, and has been marked as "Old Route 316" on some maps.

The rail bed is now part of the 20-mile Hop River State Park Trail for hiking, horseback and cycling. For years, the Route 316 crossing was a dangerous gap that required climbing down an enbankment, crossing the highway, and climbing back up the other side. A pedestrian bridge over Route 316 opened in 2012, after a decade of delays and lawsuits. (See Doug Kerr's photo of the bridge, or the links below.)