and I'm an aficionado of Dover's Strawberry Hill, Pine St, Claybrook and Sherborn's Farm, Forest and Goulding roads. Rubels maps, map my ride and the recently mentioned google and routeloops are on line resources, Charles River Wheelmen
http://www.crw.org/cgi-bin/calendar....thCalendar=yes, Bike Boston
http://www.massbike.org/newsevents/ride-listings/ and pretty much every bike shop have nice routes. For railtrails the State DCR trails folks at the State have nice trails
http://www.mass.gov/dcr/recreate/biking.htm