Western Massachusetts hilltown drive - Chester and Middlefield

In the sparsely populated areas between Pittsfield and Northampton, Massachusetts lie the hilltowns. Chances are you might not have a reason to pass through them, but they sure are pretty. Today, we're driving through Chester and then turn north to drive into Middlefield. Our directions didn't tell us about the bridge that was out, so we had to take a long-way-around over (very pothole-y) dirt roads to get to where we were going. Recorded on November 2, 2025. Thank you for watching, liking, and subscribing!