Tourists and newcomers to often complain about the confusingness of getting from one point to another in Seattle. While those who have lived in or visited cities where road plans developed more organically may have little sympathy, the heart of the weirdness of our grid system has an explanation in old time ego politics:

This pattern is the result of a disagreement between David Swinson “Doc” Maynard, whose land claim lay south of Yesler Way, and Arthur A. Denny and Carson D. Boren, whose land claims lay to the north: Maynard favored a grid based on the cardinal directions, while Denny and Boren preferred that their streets follow the Elliott Bay shoreline. Denny and Boren prevailed in what would become the central business district, but it was Maynard’s grid that ended up being extended throughout the city. [wikipedia]

I’m sure this sort of thing is discussed on the underground tour, but sometimes it’s hard to remember where the roving stand-up ends and the information begins. The article also has useful tidbits about where directionals kick in, the mnemonic for the downtown alphabetical streets, and interesting trivia like the fact that Madison is the only street that continues uninterrupted between salt water Puget Sound and freshwater Lake Washington.