The biggest problem you will run into in New England is that people are reluctant to share with those they dont know. Too many yahoos who trash the trails, litter and damager the land are causing trails to be closed left and right up here (and there are not that many to begin with).
I would say join a club but most of the clubs I've seen up here are Jeep oriented and they dont seem interested in 'easy' trails. Not sure how they expect to get more people interested in their 'sport'. Seems to me the more people they can organize and get involved the better things could be for them.
Try here
www.neow.org it's not a club but someone should be able to direct you to a club in your area. Be aware, some of the people on that board are a little abrasive and it would be better if you dont just flat out ask 'where are the trails'. It might be better if you explain your situation and what you are looking for. Also DO NOT mention any 'illegal' wheeling (or power line wheeling either) as they will jump all over you for it and will be less likely to help.
Most boards don't post trail information to keep the idiots away and keep the trails open.
I know it's not really much help. Just know most boards are not as friendly as this one.