Route 14 runs  a total of 51 miles, from Route 66 in Windham to US 6 in Providence, RI.  24.3 of those miles are in Connecticut.

Route 14 is one of those highways that really does follow an old Indian path.  Settlers in the area were pleased to find a "remarkably straight" Indian trail in Windham County, leading from Canterbury to Narragansett Bay. This trail soon served as the main street for villages in its path and was extended to Windham, then became known simply as the "Great Road."

On January 26, 1999, part of Route 14 was designated a state scenic road