Whereabouts are you in CT? I'm the Secretary/Treasurer of JT4x4 and like Billy said we do have a few private lands that we wheel. We also know of some legal dirt roads that seem to be the last roads plowed during winter that we run when we get snow. They are just dirt roads, but in snow and icy conditions they can be entertaining. Look us up.
There are NO legal trails unless you belong to a club(northeastjeep, JT, Jonfund),
There are some trails that are "Gray area" on certain days in central CT. however I'm not going to pulically annouce where they are..
Go to your local town hall or post office and get a mail a map. There are dirt roads that turn into trails and back into dirt all over the place. Legally noone can say no because they're technically still town roads if they're on the map.