A Connecticut blue blaze trail, the Shenipsit Trail is 50 miles long, starting near Somers, on the Massachusetts border, then heading south to Cobalt, CT. The end of this 6.6 mile section is on a gravel side road a few yards north of CT-140, in Ellington.
The Shenipsit Trail is a very similar to Wisconsin’s Ice Age Trail: Green, green and more green. The Ice Age Trail is a bit more up & down, whereas the Shenipsit Trail has the bigger climb, such as it is, 300 ft. up Soapstone Mountain. (A fairly steep 300 ft., as it has an equivalent grade to 1000 ft. in a mile.)
Both cross several paved roads. In the Shenipsit Trail’s case, Gulf Rd. a quarter of the way into the hike, about 1.5 miles south of the starting trailhead on CT-190. Just north of Gulf Rd., the Shenipsit Trail passes a large pond; just south of it is a trailhead for the short climb up Soapstone Mountain. If you hiked out to CT-140, then back to Gulf Rd, you would increase your mileage to 10.2 miles, without need for a shuttle.
There are two towers on Soapstone Mountain’s summit: One an observation deck, which replaced the old fire lookout in the early 70s, and a fenced off commo / radar tower. The observation deck, for that matter, is also fenced off and the bottom flight of stairs removed. You could climb to the 30 ft. or so to the top, but there is no flooring to stand on. The observation deck is covered in graffiti.
Halfway south on Shenipsit Trail is gravel Webster Rd. A quarter mile west on Webster Rd. is the Parker Rd. trailhead. An out & back hike to either CT-190 or CT-140 would get you about the same 7.1 mile hike distance, without need for a shuttle. Parker Rd. is also secluded, so your car is less likely to get broken into. (That said, Tolland County is much nicer than Bridgeport!)
If you hike this Shenipsit Trail section end-to-end and back, or do the same starting at the Parker Rd. trailhead, summiting Soapstone Mountain both ways, it would make for a very healthy 13.2 miles and 1,900 AEG day.
There are some rocky sections, but unlike the Appalachian Trail, the trail never disappears. No worries about ankle breaking or knee blowing.
The trail width varies from single track, to double track, to jeep trail. Old jeep trail in some cases, more recent jeep trail in multiple unfortunate cases south of Webster Rd. Several times between Webster Rd. and CT-140, despite blue blazed trails supposedly being foot traffic only, the surface has been so dug up by OHVs that mud bogs have formed.
There’s also a few creek crossings, but they can all be done dry, as most are no more than trickles. Your shoes will get more wet from dew.