Your best bet is to join a club. There is Jonfund And Northeast Jeep Organization in CT.
One of the first lessons I learned about wheeling is there are no legal places in CT, therefore I quickly accepted the fact I will be driving a distance to go Jeepin. If you join a club, there is some private property you can wheel on with the club. I have wheeled with the NH crew at ExporingNH.com, leaving my house at 5:00 am, wheel all day, then drive back. They have plenty of class VI roads. Getting a hotel room is always an option, or during the warm weather some people camp out.
There is Rausch creek in PA and some trails in Mass. Also there is an offroad park in Maine and another new one opening this year. One is suppose to open in New York also, not too far from CT.
I lurk on JK-forum in the New England section and have wheeled with them too.
I joined a Jeep club in Maine, as my famliy has property there. Awesome trails there and plenty of them.
The expense of traveling to wheel is part of the hobby.