I love running the hills around my little home town. Although the 40-mile rail-to-trail bike path gem cuts right through town (across my back-yard line) and there are quiet residential streets to run on, there are plenty of hills too.
I have a 2.5 mile route to a distant schoolyard that takes me up a half-mile hill on its front leg, which means it's downhill coming back as I'm tiring. I try to do each leg in under ten minutes to keep up a sub-8 pace, or at least I did before I got injured.
But the best hill in the region is half a mile from my front door, Highland Avenue, a half-mile long steady climb in one direction and a tenth of a mile precipitous climb on its other side. It has a steep side spur that, coupled with the steep climb on Highland, makes for a quarter mile "track" that enables you to run what I call boomerangs--a heavy unrelenting hill workout that absolutely saps you if you do twenty of them.
Next to Highland is the next-best hill in town, Oak Street, a fabulous incline that leads up into a dead-end where an elementary school is that also offers two sets of stairs to run on, and its end point--the furthest distance out from my front door before you have to turn back, is exactly one mile. It's also my alma mater, I went there as a kindergartner in the fifties.