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Though it's a modest, quiet route now, Route 199 does have a more colorful history.

CT 199 History

From 1932, when Connecticut renumbered all its state highways, to 1935, when US 44 was designated, today's US 44 was divided among two state routes:

During those few years, 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:

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.