I have done this ride a few times and it is wicked hilly, but load of fun on nice back country road.
I usually take the commuter rail to Westborough, MA, and then ride about 100 miles or so following the Adventure Cycling Atlantic route (
http://www.adventurecycling.org/rout...anticcoast.cfm). That route goes right through Westborough train station and drops you off at BDL.
If you have a GPS (I use Garmin Edge 705), you can download the route map from the web site and just follow your GPS.