I'll hit a couple points, that have been mentioned above but may have been lost in the fact that we're at 4 pages.
A) There is no public land available in Fairfield Cty for legal wheeling. There may be a couple of old dirt roads that get rutted but if you aren't on a legal town road, you are wheeling on private land and if you don't have the landowner's permission, you are wheeling illegally.
Illegal wheeling hurts us all. It is what the local municipalities look at, what the local residents see and what the greenie environmental groups use as ammo to close more stuff down.
Someone who lives in Fairfield Cty may own land in northwest MA (or southern VTor upstate NY, etc, etc) and when we are trying to work with a town up there to keep a road open, that Frfld Cty person will speak up at a town meeting to discourage the use and will use fear and what they have experienced (the illegal wheeling) to paint a picture of ALL 4 wheel drive enthusiasts as bad. They drag the local residents in and the next thing you know, the road gets shut down. They even complain about our kind of use on private land. Illegal wheeling will be the demise of our ability to use 4WD at all.
That segues into point
B) Joining a club.
There are about 45 clubs throughout southern New England (from NH to Long Island)
You can see some of them here: www.EC4WDA.org/RegionD
Several are here in CT. The oldest and the one with access to many parcels of private land, with permission, is Eastern 4 Wheelers. (www.eastern4wheelers.org
The cost to join a club is about $50 a year. One trespass ticket will cost about $110. Most clubs offer at least one ride a month and all of the EC4WDA clubs have an open invite to attend other clubs rides, so if you can't make your clubs ride, you can go on another. One could be wheeling every weekend. Last year, our region clubs had over 120 events on our schedule.
If you have any questions, please don't hesitate to ask.