Once deemed by Ripley’s Believe It or Not to be the “Crookedest Street In The World,” Iowa’s Snake Alley was created in 1894 by a trio of German immigrants. The steep street was constructed with a purposeful design, meant to mimic the vineyard trails of Europe.

Aside from aesthetic choices, the street also served to connect Burlington’s downtown business district to a residential area on the raised end of Snake Alley.  The street consists of nearly 300 feet of five half-curves and two quarter-curves. The dizzying zig-zag proved too much for the horses that it was initially intended for. Limestone bricks that make up the street’s surface were decidedly placed at an angle, to help the beasts keep a footing.

Speaking of horses in Snake Alley, there is a (likely apocryphal) story that after it was completed, the Burlington fire department would send prospective horses down the road at a full gallop and those that didn’t tumble over themselves, break ankles, or otherwise collapse would be allowed to pull the fire trucks. 

Today, the road is home to an annual bike race and art fair.