There is also a lot where the trail crosses Route 23 to the east of Great Barrington (probably a bit further from town, though), as the trail itself kind of circles around town and doesn't go too close to it (not like it does farther north where it goes right through towns like Dalton and Cheshire).
I also thought the trail crossed 7 to the north of Kellogg, then ran parallel to the stream along the fields down to it before walking along the road (Kellogg) itself for a bit then crossing another road and back into the woods?