From 1932 to 1935, Route 199 was the number for the portion of US 44 leading west from US 7 into New York state. The rest of today's US 44 was part of the old Route 101.

At the time, today's Route 199 was called Route 131.

In 1935, US 44 was created, and routes 101, 131 and 199 were moved. Route 199 was now 9.30 miles long, as shown from south to north:

• South St., from Roxbury Falls to Route 67
• Overlap with Route 67 to North St.
• North St. and Roxbury Rd. to Route 47 (this segment is today's Route 199)

In 1951, a segment leading from Route 67 (now SR 867 at Bridgewater Center was added, along Hut Hill Road and Minor Bridge Road, connecting to Route 199's south end. The new route, 12.37 miles long, followed a "U" shape south of Route 67, which it intersected twice.

The Roxbury Garnet Mine is one of the industries that led to several Connecticut boom towns in the past that are largely ghost towns now. No state highway serves Roxbury Falls now, and it appears that in the 1950s the state was looking to turn over that portion of Route 199 to the town. The entire route disappeared from the official state map in 1957 and 1959, though it reappeared in 1960 with a different cartographer.

In 1963, all of Route 199 south of Route 67 was turned over to town maintenance.

• Bridgewater Roads
• Route 199 Ends (Photos; Doug Kerr at state-ends.com)
• Route 199 - Google Maps