High Quality Content by WIKIPEDIA articles! Route 8 is the portion of the multistate New England Route 8 within the state of Connecticut. It is a 67.34-mile (108.37 km) state highway running north–south from Bridgeport, through Waterbury, all the way to the Massachusetts state line where it continues as Route 8. Most of the highway is a 4-lane freeway but the northernmost 8.8 miles (14.2 km) is a 2-lane surface road.