Connecticut State Route 8 is an freeway in the western part of Connecticut. There is a brief portions of CT St Rt 8, fron Winsted to the Connecticut/Massachusetts State Line, near North Colebrook, that is a two lane highway. CT St Rt 8 runs from Bridgeport to the Connecticut/Massachusetts State Line, near North Colebrook. Info on CT St Rt 8 is broken down by county below. Fairfield County New Haven County Litchfield County