Hillman Herbert Cooper 38" “Kangaroo” 1886
The “Roo” was one of the first successful commercial designs using a chain drive to gear up the drive wheel. Using a 38 inch diameter driving wheel geared-up to 54 inches, this H.H.C. "Kangaroo" dates to 1885. Many builders offered this type of machine commonly referred to as a ”dwarf safety”. A rider would avoid a major spill due to a lower center of gravity, the rider being closer to the road.
Below is an image of the Wakefield Bicycle Club, Wakefield Massachusetts. The member at the center holds a "Kangaroo".