I'm not 100% sure but I think you can sail in the Quabbin Reservoir as long as you stay a certain distance from the dam/dike. Also a possibility is Lake Champlain up on the VT/NY border. That might be a hike for you though. Oh, and people sail the CT river up in Greenfield upriver of the Turners Falls Dam. They even have some buoy lines
so you don't get too close to the dam. Happy sailing!