The 1970s were a troubled time for the American economy. Inflation was high, companies were unstable, and the unemployment rate at the end of the decade was the highest recorded since the Great Depression. The closing of the Winchester area's largest John Deere dealership left long time service manager, Doyle Whittington, in the ranks of the unemployed. Unable to wait the months that it would take for a new dealership to open in the area, Doyle decided to strike out on his own in July 1980. New Safemark tire dealer - 1985

The early days were difficult. Starting with but nothing experience and reputation, Doyle began by repairing the dealership's former customers' equipment in his own driveway. Working alone on the repair side meant that his wife, Jean would be needed as bookkeeper. The two worked together at their home for several months until Doyle's Equipment Service was officially formed, and operation was moved into an old service station on US 522 one mile north of Winchester. The two continued to grow the business, hiring mechanics to assist with repairs and counting on word-of-mouth advertising to bring in new customers.

The company had found its stride by 1984 and a larger repair facility was needed. In October of that year, Doyle's Equipment moved to its current location on Commercial Street in Winchester. With a larger building that included a showroom that once displayed Oldsmobiles, Doyle was ready to expand into sales. In the fall of 1984, Doyle's Equipment began carrying Toro brand lawn care equipment. It was then that Doyle's began their longstanding tradition of offering the best quality products backed by first class service. The Wheel Horse line of garden tractors was added in 1989, and Lawn-Boy walk power mowers were added in 1994. Maruyama commercial handheld equipment was picked up in 2000.

The company has continued to grow on its reputation of friendly service, dependable know-how, and reasonable prices.