Began as Colorado Springs Harley-Davidson in 1934 and was located in 3,500 square feet in "Motor City", the local "Auto Row." In that first year they sold approximately 20 motorcycles and a few parts. It changed ownership in 1955 to the Newell family.

Pikes Peak Harley-Davidson, Inc. was purchased from the Newell's in 1986 by the partnership of John and Lynn Cockson and Alan and Connie Bond. They were in a building of approximately 4,000 square feet located on E. Platte and employed 3 of the 4 owners plus 2 others. The business was moved to larger facility of 7,000 square feet. In 1992, the business was again moved to a 2 - story strip mall and is a 14,170 square foot Generation II Designer Store, with an added 2,200 ft. square of storage on a separate lower level. The building was located at Powers and N. Carefree.

In 1995, Herb and Sunny Aston purchased the dealership when they moved to Colorado Springs from Milwaukee, where Herb was Harley-Davidson's Director of Worldwide Training.

In 2001, the business was again moved to a new, much larger building on 7 acres of land on north Nevada, close to the I-25 and Nevada interchange. The building has over 40,000 square feet with an 1800's gold mining theme in the main showroom.