Driving directions between Bridgeport, CT and Pittsfield, MA. Estimated driving time is , with an average speed of about 48 miles per hour. If you want more accurate directions from your actual position or to a certain place or street, you may search street or place names directly.
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Find the directions listed below in order to go from Bridgeport, CT to Pittsfield, MA by car. You can click each direction to see them in the map.
CT 8 $north, James H. Darcey Memorial Highway
103.3 mi2 hours 7 mins
| Head north on Ellis Lane | 100 feet | |
| Turn right onto George Street | 300 feet | |
| Turn right onto Main Street | 200 feet | |
| Keep left onto Main Street | 500 feet | |
| Make a sharp left | 400 feet | |
| Take the ramp towards CT 8: Trumbull | 0.3 mi | |
| Merge left onto CT 8 N | 2.0 mi | |
| Keep right onto CT 8 N | 54.8 mi | |
| Turn right onto South Main Street (US 44) | 0.3 mi | |
| Turn right onto Park Place (CT 8 N) | 900 feet | |
| Go straight onto North Main Street (CT 8) | 1.7 mi | |
| Continue onto Colebrook River Road (CT 8) | 6.7 mi | |
| Continue onto South Main Street (MA 8) | 8.0 mi | |
| Continue onto South Main Road (MA 8) | 8.6 mi | |
| Continue onto Otis Road (MA 8) | 1.1 mi | |
| Turn left onto Jacobs Ladder Road (US 20) | 2.6 mi | |
| Continue onto Cape Street (US 20) | 3.1 mi | |
| Continue onto Chapel Street (US 20) | 0.5 mi | |
| Continue onto Water Street (US 20) | 0.7 mi | |
| Continue onto Housatonic Street (US 20) | 0.7 mi | |
| Continue onto Park Street (US 20) | 600 feet | |
| Turn right onto Main Street (US 20) | 0.4 mi | |
| Make a slight left onto West Center Street (US 20) | 1,000 feet | |
| Continue onto Laurel Street (US 20) | 1.2 mi | |
| Continue onto Lee Road (US 20) | 1.2 mi | |
| Continue onto Veterans Memorial Highway (US 7) | 2.1 mi | |
| Continue onto Pittsfield Road (US 7) | 2.0 mi | |
| Turn right onto Holmes Road | 3.5 mi | |
| Keep left onto Holmes Road | 100 feet | |
| Go straight onto Elm Street | 0.6 mi | |
| Go straight onto Fourth Street | 0.2 mi | |
| Turn left onto Lanckton Court | 100 feet | |
| You have arrived at your destination, straight ahead |