Alphabetical City-Jumping (starting at NYC, 100k+ cities)
Start in New York City (with a Y at the end).
Find the closest city with population 100k+ starting with the last letter of New York City.
Next, now take your new city, and find the closest city (to the city you just found) with population 100k+ starting with the last letter of the city you just found.
Continue until you reach a caveat (either a city starting or ending in the same letter, or the repetition of a city in the list.)