Grover Sassaman first attended Harley-Davidson® Factory School in 1939, where he began his lasting relationship with the Harley-Davidson® Company. He was signed as a dealer in Indiana by Arthur Davidson, and later was relocated to Lakeland Florida in 1947 under the name of Sassaman's Motorcycle Co. In 1957, the Company moved again to Second Street in Macon, Georgia. Grover's sons- Greg and Gary Sassaman grew up in the business, and have been involved with the brand ever since. From 1974-1978, Greg Sassaman raced professionally for the Harley-Davidson® Factory Dirt Track and Road Race Teams, earning National wins and championships.

The business made its final move to its current location on Mercer University Dr. in 1973. When Greg left the pro racing circuit and came to work with his father in the late '70s, Greg didn't immediately step into a management role. He worked as a technician in the service department and in parts. Eventually he took over the reins from his father, and his brother came to work for the company. One of the biggest projects for Harley-Davidson® of Macon has been the remodeling overhaul of the dealership. The previous site from '73 was a cramped 12,000 square feet. The new building was built literally on top of the old building in 2002. The dealership remained open through the entire year of construction. The new showroom is almost four times as large as the old showroom - and business continues to grow today.