1913 Scripps-Booth Bi-Autogo
"The Bi-Autogo was the world's first large, experimental, two-wheeled automobile. It was… powered by the first automotive V-8 engine built in Detroit." The large drive wheel is barely visible at the rear. The small wheels can be lowered when the machine is at rest or to provide stability at low speeds.
The Owls Head Transportation Museum in Maine www.ohtm.org/edu_col.html