I'm in Rochester, NY (Bicycling Magazine's #50 best cycling city, I'll have you know
) and I pretty much ride everywhere withing a 60 mile radius of the city.
There's a lot of different road routes in this area and I usually plan out my longer rides using veloroutes.org the before.
One thing about Rochester is that it's relatively flat and you need to go pretty far Southeast before you get to any significant climbs. This summer I plan to take a trip up to the Burlington, VT area to tackle some real mountains!