2. Yesler Way

This street was created to serve Henry Yesler's sawmill on Elliott Bay, and was therefore originally called Mill Street. Legend has it that logs were once dragged down it from First Hill, giving it the nickname "Skid Road," although there is little hard evidence of such activity. Early in Seattle's history, Yesler Way became a moral divide separating a southern vice district of saloons and brothels from "respectable" areas on the north. The Rev. Mark Matthews, a crusading reformer and prohibitionist, popularized the phrase Skid Road in the 1920s to dramatize the sinful ways and traps south of Yesler.

Yesler Way also divided the pioneer claims of Arthur Denny and Carson Boren on the north and David "Doc" Maynard on the south. When Denny and Maynard sat down to draw up the first plats for Seattle in May 1853, they could not agree on the orientation of the street grid. Denny later grumbled that Maynard, "stimulated with liquor," had decided he was "not only monarch of all he surveyed, but of what Boren and I surveyed, too." Their spat survives in the tangled intersections along Yesler Way.