You could start by taking the commuter train to Worcester from Boston(off peak). Get the Rubels bike maps for the entire state. You could ride through Worcester to Sturbridge (rt 20) to Springfield and North on Rt 5 to Northhampton to Rt. 9 into the Berkshires. if you plan to come into Springfield let me know via e-mail and you could camp in my yard. I could ride with you up to NHampton. I rode from worcester to Spfld 2x, rolling to hilly & flat.
Ed