Route 14 begins at a junction with Route 66 (Main Street) in Willimantic, initially as Main Street which changes to Brick Top Road after . The road runs through Windham Center and briefly overlaps Route 203 as North Road, shifting to Scotland Road as it heads into the town of Scotland. In Scotland, Route 14 is known as Huntington Road and Palmer Road. It also overlaps Route 97 for 0.68 miles (1.09 km) from the eastern section of town to the center of it.