Good point, however locale and time certainly have something to do with it. I live in central Connecticut, somewhat scenic, some nice area's, places to camp etc. but nothing that would really make me so inclined to go out and spend the night as opposed to just going out for a nice ride, especially if I have to fork out $20 to camp for a night. The same is probably true of you in Boston, likely more-so. To take advantage of some of the nicer places to camp in the region (Berkshires, Vt, etc.) do require a bit of planning.
Of course I can't speak from personal experience, which is probably my problem right there. In the spring I'll have to just go out and give it a try on some Friday/Saturday, if of course, this snow ever melts