I went North to South on the Metacomet Trail in CT during a supported attempt of the CUT 112 on 6/2/18. Since this is mostly trail, I'm going to propose that the trail ends on Orchard Road, rather than including a 2 mile road section at the end. The second 30 miles of this is pretty rough, even without any massive climbs. It is just consistently technical and unrelenting.
Flagged: Ben unintentionally short-cut a section of the trail just north of Shuttle Meadow Reservoir. It is evident from his GPS that he was having navigation difficulties in that area. He ran a direct route along a gas line, instead of the more meandering Metacomet Trail. His route is roughly 0.7 miles shorter than the Metacomet route, over a ~3 mile section.