Here is a heatmap of all the cycling I've ever done. For the time being, I've only ever biked in and around Boston, so it's nicely compact. My goal is to hit every neighborhood and major road en route to exploring all of Boston via bike. It's the best way to see the city and all the little nooks and crannies hidden throughout. Next up are Cambridge/Somerville, East Boston, and Jamaica Plain once the weather warms back up. 

You can see that most of biking is restricted to downtown, Back Bay, Brookline, and Brighton (where I live). I often take a longer, alternate route to work through Cambridge in the mornings, and there are some spots that I frequent, like Castle Island, Seaport, and the Emerald Necklace. 

Then there are some of the longer excursions I've taken: the Boston Marathon route out to Hopkinton (and once to a nearby apple orchard a bit further out), up to Salem, up to Pelham (the closest town in New Hampshire), and my first century through Harvard/Acton/Weston to the northwest. This spring/summer I'd to add even more tendrils like these, for example out to Providence, Manchester by the Sea, and maybe Brockton.