Sherry Schaefer is a Greenville, Illinois, native and grew up around tractors and equipment. Her grandfather, Ervin Schaefer, was an Oliver tractor dealer and her father, Oliver “Ollie” Schaefer, is a used Oliver tractor and equipment dealer in Greenville, Illinois. The Schaefer family also owned and operated a national tractor pulling sled service for more than 25 years beginning in the late 1960s. In 1993, Schaefer became the editor of the Hart-Parr Oliver Collector’s magazine. Schaefer began her own bi-monthly Oliver publication in 2004 and started Heritage Iron magazine in 2008.

Schaefer has authored numerous books, and has provided her expertise to dozens of other tractor-related books. In 2003, Schaefer assisted the Smithsonian Institution with the restoration of the oldest mass-production gasoline tractor in existence. Schaefer is a past vice-president of Farm Rescue and currently serves as vice-president of the Greenville Airport Authority. As an instrument-rated pilot, she is able to utilize her other passion, aviation, into her business by flying herself to many of her interviews and tractor events.