According to Google, Poultney is an hour and a half from either ALB, BTV or LEB, but three hours from MHT or BDL, three and a half from BOS, or four and a half from JFK.
With those timings, I'd suggest taking your pick between getting a flight with one change to ALB/BTV or a nonstop flight to BOS. The total journey time is likely to be very similar. (As a rule of thumb, a connection on a transcon generally adds about two hours to the total journey time.)
Unfortunately, I don't think anyone is operating the SJC-BOS 'nerd bird' any more (which is a source of considerable angst to my colleagues!) so for a nonstopper you'd have to go to SFO, where they're fairly plentiful. More likely you'd take one of many possibilities from SJC to ALB. Most airlines will do that with one connection somewhere in the Midwest.