Here are links to sites that provide maps, weather and traffic reports, cycling rules and regulations, rules for riding safely in traffic, and alert you to opportunities for fun on a bike outside the scope of Get Up'N Go.
First and foremost, the state's regulations and requirements regarding the use of bicycles, embodied in M.G.L. Chapter 85, section 11B.
Then there's John Allen's classic manual for surviving in traffic.
And, of course, the sure way to acquire driving directions, MapQuest.
For making decisions about the weather we rely first on NOAA's (National Oceanic and Atmospheric Administration) Doppler radar images; these are very handy for predicting whether precipitation's likely to happen when and where we'll be walking or riding. The Weather Channel offers hour-by-hour and town-by-town forecasts, useful but, because they're invariably couched in terms of the probability of precipitation (it might rain or it might not), not as helpful as knowing that it's raining right now in Fitchburg and the front will reach Weston in half an hour, something easily divined from NOAA's radar data.
Before driving to a starting location involving a major suburban highway, we always check with SmarTraveler to see whether there are traffic delays.
We have a Groton-Westford-based sister organization, AdventuRides, staffed by a couple who stepped up to the plate when Get Up'N Go handed off its far western suburban rides in favor of augmenting those closer to Boston. Check them out if you live on the western fringes of our territory or can afford a longer than half hour drive to the start. AdventuRides offers terrific country riding.
If the road is your thing and you're looking for organized "touring" rides up to a hundred miles or more, visit the Charles River Wheelmen, the area's largest cycling-related group and one devoted specifically to low-octane road rides. From time-to-time the CRW also offers weekend rides based on various New England inns. We're members and will happily get you started with CRW if you need a nudge.
Boston has many strong bicycle racing clubs offering weekly training rides. These heavy duty events are outside (far outside!) Get Up'N's scope, but we're active members of one of them, The Northeast Bicycle Club, known for its efforts to prepare new riders for the rigors of road racing. Think you might want to give racing a try? Let us know. Maybe we can help.