In the 1920s, the road from the northeast corner of Stonington (at New England Route 17) heading north through North Stonington and Voluntown to the Sterling Hill section of Sterling was designated as State Highway 216. In the 1932 state highway renumbering, State Highway 216 was renumbered to Route 95.[5][6] In 1950, Route 95 was extended east along modern Route 14A up to the Rhode Island state line.[7] In 1958, Interstate 95 was formally designated in Connecticut, and Route 95 was in need of a new designation due to the numbering conflict. The new designation chosen was Route 49.[5] In 1963, as a result of the Route Reclassification Act, Route 14A was created and the north end of Route 49 was relocated to its current terminus.[5]
In early 2003, work on Route 49 and Route 14A Corridor Management Plan was started, funded by the FHWA and ConnDOT. The concerns are speed along Route 49, stone walls, and the surrounding scenery. Since state budget constraints preclude adding more police, one idea was to repaint the fog line so that the lanes are 11 feet (3.4 m) wide.[5] In October 2003, the state turned down a N. Stonington request to lower the speed limit from 45 mph (72 km/h) to 35 and 30 mph (48 km/h).[5]