Snake Alley; Burlington, IA
San Francisco, Schmam Francisco. If you're looking for steep and winding roads (and the bicycle ride of your life), head to Snake Alley. Ripley's Believe It or Not, noting the road's sharp turns and slope, dubbed Snake Alley "The Crookedest Street In The World," ahead of San Francisco's famed Lombard Street. The alley — developed in 1894 by German immigrants — has a total of five half-curves and two quarter-curves spanning a 275-foot distance. Ironically, the street was intended to provide "a more direct link" between businesses and shops, according to the road's website. However, Snake Alley, once considered "a triumph in practical engineering," proved to be impractical for horse carriages. The town abandoned plans for more roads with the same design, making Snake Alley one of a kind (at least in Burlington).