By valley you mean Housatonic and not CT river valley right?
I'm in Trumbull - would be into meeting up with fellow jeepers for whatever... there is the meetups on Friday nights at heavenly donuts that I never went to. They have a facebook group in case you weren't aware of that.
If you are looking to start a club it may be much easier to join an already established club. CT has numerous clubs that belong to larger offroad associations that promote legal wheeling. By joining an already established club you gain access to a large amount of trails and large events put on by the associations!
NEA4wd associated CT clubs
Central CT 4 Wheelers
East Coast Offroad Jeepers Of Connecticut
Northeast Jeep Organization
NOVA4x4 associated CT clubs
Eastern 4 Wheelers
East Coast Off-Road Jeepers of Connecticut
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