The Tailwind is the third in a series of high-wing aircraft designed by Sylvester J. "Steve" Wittman (1904–1995), a well-known air racing pilot and race plane designer, who also played an important role in the emergence of homebuilt aircraft with the Wittman Tailwind and other designs in the United States.
The first, the Wittman Buttercup two-seater, and later the Wittman Big X four-seater, which was bought by Cessna to use its spring steel landing gear.
The Tailwind also inspired the last iteration, the O and O Special.
A model of the 1965 Wittman Tailwind may be found in the Sun 'n Fun Museum.

Wittman developed the C-85 powered "Flying Carpet" in 1953, later renaming it to the "Tailwind".
In 1953, the Tailwind became the first aircraft covered under the FAA's Experimental category to be certified to carry a passenger.
While crude looking by modern standards, it outperformed many similar factory-built planes, and only with the advent of composite construction were new designs able to achieve similar speed per horsepower and range.

Steve Wittman and his wife were killed April 27, 1995 when their "O&O Special", a similar, larger and one-of-a-kind aircraft crashed.
The propeller and some fabric covering from this "O&O Special" is on display in the Wittman hangar located on the Pioneer Airport, Oshkosh, Wisconsin.

Aircraft Spruce & Specialty Co of Corona, California acquired the rights to the Tailwind in January 1996 and became the exclusive distributor for plans and materials.
The Tailwind is the third in a series of high-wing aircraft designed by Sylvester J. "Steve" Wittman (1904–1995), a well-known air racing pilot and race plane designer, who also played an important role in the emergence of homebuilt aircraft with the Wittman Tailwind and other designs in the United States. The first, the Wittman Buttercup two-seater, and later the Wittman Big X four-seater, which was bought by Cessna to use its spring steel landing gear. The Tailwind also inspired the last iteration, the O and O Special. A model of the 1965 Wittman Tailwind may be found in the Sun 'n Fun Museum.
Wittman developed the C-85 powered "Flying Carpet" in 1953, later renaming it to the "Tailwind". In 1953, the Tailwind became the first aircraft covered under the FAA's Experimental category to be certified to carry a passenger. While crude looking by modern standards, it outperformed many similar factory-built planes, and only with the advent of composite construction were new designs able to achieve similar speed per horsepower and range.
Steve Wittman and his wife were killed April 27, 1995 when their "O&O Special", a similar, larger and one-of-a-kind aircraft crashed. The propeller and some fabric covering from this "O&O Special" is on display in the Wittman hangar located on the Pioneer Airport, Oshkosh, Wisconsin.
Aircraft Spruce & Specialty Co of Corona, California acquired the rights to the Tailwind in January 1996 and became the exclusive distributor for plans and materials.
Wittman Tailwind