Obligatory Tom7 recommendation: [How I ran the length of every street in Pittsburgh: PAC TOM](https://www.youtube.com/watch?v=1c8i5SABqwU).
In this "expert mode running" video the protagonist, Tom Murphy VII, of computer science comedy YouTube fame, runs 3661 miles across 269 runs in this mammoth 16 year project to run every street in Pittsburgh, thus "completing" it Pac Man style.
If you are not familiar with Tom7 and his whimsy, I cannot recommend enough that you check his videos out.