1816: The Walking Machine
The German Baron Karl von Drais de Sauerbrun invented a walking machine that helped him scoot around the royal gardens faster. It basically was a scooter with a seat. It featured in-line wheels mounted in a frame and had no pedals or cranks. He patented the wooden machine as the Draisienne and it became known as the hobby horse.
1855: The Boneshaker
The origins and exact timing of the next generation of two-wheeled riding machines aren’t clear. The Frenchman Pierre Michaux reportedly had the idea to attach an axle to the front wheel of a walking machine, so the wheels could be turned by the rider’s feet. The machine was dubbed the Velocipede but most people called it the Boneshaker.
1870: The High Wheel
People soon realized the bigger the front wheel on the Velocipede, the faster the ride. The High Wheel bicycle was born. Bicycles cost an average worker six months’ pay. That, combined with the danger, made High Wheels mainly a plaything for rich men.
1885: Rover Safety Bicycle
John Kemp Starley, an English inventor, scaled down the front wheel and added a chain-driven rear wheel. This made the bicycle safer and faster, and the design, along with the invention of the pneumatic tire, brought down the cost and launched the bike craze.
Sources: Pedaling History, Owls Head Transportation Museum, Modern World