In our rural area, there are a number of places that show up on the town maps as 'roads' but they are nothing more than a cow path thru a field on a farm. Somewhere along the way when the maps were translated to the GPS realm, some of them weren't removed. So if you come to visit us, there are a couple places where blindly following the GPS could put you in the middle of a field surrounded by cows.
And a bit further up north, near my friends house, is the famous Smugglers Notch on Mt. Mansfield. There's a road, which closes for the winter. It's very narrow and at one point, its exactly one car wide with rocks on both sides. There have been a number of instances this year where trucks have gotten stuck because they have to follow the optimized time/distance route that their GPS system tells them to go, and that system tells them to use the Notch, despite all the 'no trucks allowed' signs, and unfortunately, some don't pay attention when they should.