Great Hill Mountain Loop is a 3.7 mile loop trail located near Cobalt, CT that offers scenic views. The trail is rated as moderate and primarily used for hiking.
If you start on the road with the blue-marked trail head (starts where the tree is marked with two blue streaks with parking for two/three cars across the street) it starts pretty flat and gradually gets steeper and steeper. Once you hit the top (you'll know because there will be an option to go left or right) take a left. We went right and it seemed like it was descending so we turned around and continued in the opposite direction. Soon we were brought to an overlook obstructed by a few trees (as expected in nature). We descended on an un-marked route that took you to a different road than the one we started on. And the area we came out of had two other routes taking you into the woods - all three were unmarked. We used GPS and walked back to the road we started on.
Beautiful trail - I always hike the Shenipiset trail up to the Great Hill Mtn. lookout. Nice quick hike about 3.5 miles (1.5 - 2 hours) up and back w/ some steeper sections, but nothing to strenuous. Well maintained and well marked w/ blue blazes. Beautiful views all along the ridge of the trail and obviously from the lookout - almost like you could dive right into Great Hill Lake.