Route 14A was created in the Small Renumbering, circa 1963. Before that, portions of it had the following numbers:

• Canterbury Road and Railroad Avenue, from Route 14 to Route 12 in Plainfield: Route 14 (the earlier alignment)
• Plainfield Pike Road, from Route 12 in Plainfield to Route 49 in Sterling: unposted SR 586
• Plainfield Pike, Sterling: Route 211 (1932-1950); part of Route 95 (1950-1960); then part of Route 49 (to 1963).

Early 2000s: reconstructed in Plainfield

A three-mile section of Route 14A, from I-395 to the Sterling town line, was reconstructed from summer 2002 through spring 2005. The existing narrow, winding road, known as the Plainfield Pike, had blind curves, winding hills, and (to top it off), heavy truck traffic.

After the $6.5 million project, the reconstructed Route 14A is straighter and less hilly, and a uniform 40 feet wide including shoulders.

"Two projects, one fairly interesting, are continuing in Northeastern Connecticut if anyones taking a road trip in the area soon.

"CT 101 just east of CT 169 is having approx. 1 mile widened & straightened. The road was cut into a hillside, so it's taking quite a bit of fill to straighten. But otherwise kinda unremarkable.

"The more interesting construction is CT 14-A from approx. 1 mile east of I-395 to CT 49 is being rebuilt, and there is still a few sections of the old roadway in place for comparison.

"It's kind of a bummer that 14-A is being rebuilt, as that was on my list of where to drive the first weekend I finally own a BMW :) It was a twisty, up and down road that really gave you a ride, and heavily shaded as well...just a fun road to drive on if you're not trying to go anywhere in particular in any given time.

"It's being rebuilt as a more typical modern state highway, straighter, no up-and-down dips, big curve radiuses, and wide shoulders. Lots of fills, some cuts, and temporary gravel sections."

Matt Kivela, post to misc.transport.road, May 5, 2003

• "Route 14A safety improvements begin." Norwich [Conn.] Bulletin, June 12, 2002.
• "Crews begin to unravel Route 14A." Norwich [Conn.] Bulletin, August 5, 2002.

Thanks to Wm. F. Yurasko for several sources.