I'm in Derby. I went up to Nepaug last fall on a scouting mission in my WJ by myself. The trails are simple, like someone said, most can be driven in a Civic. It is good for a first timer or someone looking to put around in the woods.
I did almost get stuck in a mud pit on one of the off-shoot trails. Luckily I didn't get stuck or get in trouble. Since it is about an hour and change for me to get there, I can't say there is anything of interest up there for me now.
One thing I HIGHLY recommend in there (as is true with any forest/woods) is a GPS..Preferably a hand held one that can track your path. I know the factory Mopar GPS has a "Trail" function that lays down a bread crumb trail so you can at least follow your path out. I have a hand held one and still got turned around in there. If I remember correctly, many of the trails do show on the GPS.
I am really on the hunt to make friends with someone with some private land and have also pondered joining a club, but haven't pulled the trigger on that yet. I hear that the powerlines in MA (unlike CT) are considered "public". With that said, I have heard of trails/powerlines just over the NW CT border. Someone please correct me if I am wrong here.
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2010 JK & 2004 WJ