Arlington has a lot of private ways that are in similar states of disrepair (hey, that's part of the area's charm). The kids like it when I take one of them as shortcut to our house; as the vehicle rocks back and forth, they cry out “whoahoo ! whaohoo ! whoah !”
There's also a fairly old segment of a street close the geographic middle of town; it's only about a hundred feet in length, but while you're on it it's like driving up the side of mountain, and yet you're in the middle of a town which has very little open space.
I can remember when my mom would take us to some swimming hole in her early-60s model Chevy sedan, and it was like magic once the woods enclosed the vehicle and the adventure of the bumpy road began.