His father was CEO of Utah Construction Company, his mother is a strong supporter of the arts and a member of the Chairman's Council of the San Francisco Opera.

He obtained his first full-size military vehicle in 1975, a World War II era M3 Scout Car.

He worked for Hewlett Packard for five years as a manufacturing engineer before focusing solely on building his museum and restoration facility.

Littlefield served on the boards of the General George Patton Museum, the Cate School, the Coyote Point Museum for Environmental Education, the Hoover Institution, the California Academy of Sciences, and the Filoli Center.

[4] The American Heritage Museum at the Collings Foundation headquarters in Stow, Massachusetts, had its grand opening in May 2019 and displays over 85 vehicles of the Littlefield collection.