Sunday 1/8/17 decided to go SnowShoeing with a friend at Diamond Hill. The Town did a wonderful job marking the trails, there are now "marked trails" at Diamond Hill. We ended up on the pink trail till it just seemed to end, looked like it was the back of someone's yard, we weren't sure if we were on private property so we turned around and went back. We did about 4.16 miles on the trails, lots of good hills to get the heart pumping. Would like to explore more. I would believe the trails back there would lead to Joe's Rock in Wretham?
I agree with several earlier reviews that the trails are not very well marked in many places. Still, it's pretty tough to really get lost -- and the diversity of terrain (and difficulty levels) and natural beauty still make this a well-deserved repeat hike! Overall, perhaps, a "moderate" rating may be appropriate: but there are many -- many! -- sections that are very challenging, both up and down. I strongly advise bringing good trekking-hiking poles with you, and plan to take periodic breaks along the way. (I also don't recommend hiking this when the temperatures are in the mid-90's with high humidity. . . learn from my dumb mistake!)