The first tall bike in Portland was probably a mid-1800s High Wheeler. Designed to replace horses, and presenting their riders at a similar height, these penny-farthing bicycles launched an international bicycle boom at a time when Portland was becoming an important West Coast port. Portland patriarch Henry Pittock, a wealthy industrialist and avid bicyclist, was likely among the many upper-class Portlanders to embrace this early style of bicycling.

Even after the diamond-framed "safety bicycle" superseded the high-wheeler, tall bikes had their uses. At the dawn of the 20th century, lamplighters were using purpose-built tall bikes on their rounds in some cities, lighting and extinguishing gas lanterns high above the street. Throughout the century, bicycle shops used tall bikes as rolling advertisements, and circuses embraced them for acrobatic shows and parades. In 1964, Popular Mechanics Magazine published plans for a tall bike that required no welding, launching a mini-boom of "upside-down" tall bikes built by home tinkers.