Well you have NH, VT, Maine, Mass, RI and CT all around you so there is never a shortage of places to go for a days ride. By day I guess you are thinking 300-400 mile rides? (backroads not highway). If so then there are plenty of choices - get "Motorcycling in New England" from Whitehorse Press or look at old issues online of RoadRunner magazine to give you a few ideas.
A few classics such as taking Rt 60 to the Ouabbain reservoir via Barre (stopping for lunch/coffee at the cafe on the corner), loop the reservoir and come back via Rt 9 heading North or South to avoid Worcester (never ever drive through here on a weekend). Another would be Rt 119 (if you have time) all the way to Brattelboro, NH (taking Rt 2 back to get home if in a hurry) then up Rt 100 to Woodstock for example then take Rt 4 east to NH and come down Rt 124S or Rt63S for some scenic roads. Plenty more when you look at any map.
Andy (also in Boston and work in Waltham and ride most days to work).
(beer night once a month in the Greater Boston area)