A close second in the "Confusing to Newcomers" street awards would be Braddock and West Braddock roads. Braddock is west of West Braddock, and the two do not connect. But I get it, NoVA! Joke's on me! Good one!
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You: Guy fishing in sewage-infested 4 Mile Run yesterday by the Rt. 1 underpasses. I stopped to make sure you had heard about the sewage spill and the notice to avoid the water. You said you had, and that everything was fine because you were wearing latex gloves.
Me: Thoroughly grossed out, but at least able to ride on with a clear conscience.
If you want missed connections, you can't do much better than this. My old realtor lived on 26th St N and it took me half an hour to find her house for the first time. Click that link and see how many roads, places, or streets named 25th you can find that don't connect to each other.
I'm from Charlotte. I have no sympathy for street naming wusses. One of the main intersections is Providence-Providence-Queens-and-Queens -- where you change streets if you go straight. And don't get me started with the Sharons this map doesn't do them justice(Sharon Rd, Sharon Ln, Sharon Rd West, Sharon View, all of which are major roads that you have to turn at least once to stay on).
I used to live on 12th St. S.http://goo.gl/maps/TF0LL The 12th St. S that intersects with Columbus St. Not the one that connects with S. Frederick. And continuing West...not the one that connects with Quincy or S. Glebe or Courthouse Rd. or S. Queen or S. Hayes or S. Eades. Between Rte. 7 and the Potomac you could hit a dozen 12th St. Souths that I didn't live on.
I could not get food delivered.