Jake and Ruth started a riding club known as the Pleasure Riders Motorcycle Club in 1958 which was approved by the American Motorcycle Association. They hosted annual hillclimbs each year for fundraising. The club also hosted field days and road events for pleasure riding. Jake and Ruth were very avid race fans also. When the races were in the area, there was always a group of motorcycles leaving the shop for the race.

Their family consisted of James Robert, Michael Ray, and Barbara Ellen Gutterridge. The Gutterridges were seen frequently in their sidecar outfit riding about the country. Jim worked in the shop as a boy, but went to college at Southern Illinois University. He returned to Danville, Illinois working at Hyster for a short period and then moved away from the area. Barbara married Raymond Wright and lives in the area, but does not continue to work at the shop. Michael, however, could not get away from the family business. He married Beth, and tried working in local factories, but came back to work as Manager of Business in 1973. Beth started working full time in the business in 1996 as the Office Manager, after raising their two wonderful boys and holding down many prominent positions at the Vermilion County Court House and 118 School District in Danville, Illinois.

The new first showroom addition was added to the existing building in 1973, which is the present motorcycle and parts counter area of the current dealership. The new facility allowed more room for the display of motorcycles and accessories. The addition also included a full reality office which Jake owned. Michael purchased the business from Jake and Ruth, and became the sole proprietor in 1979. Ruth continued to work for Michael for many years as a bookkeeper until she retired. The Middlefork Valley Harley Owners Group (H.O.G.) was established in 1988.

Michael and Beth raised two boys, Troy and Roger, in the business. They were avid motorcycle racers, and destroyed many bicycles learning to ride the way they do. Troy went to Southern Illinois University where he played for the Division 1AA Salukis as a punter and place-kicker. He earned two letters and a scholarship. In May 1991, Troy secured a position with Harley-Davidson Motor Company's Service Department in their Juneau Avenue home offices in Milwaukee, Wisconsin. Troy has two children named Courtney Anne and Brooke Lindsay. They are very much interested in supporting the Harley-Davidson tradition because they love motorcycles and can be seen riding all over the country with their dad. Troy was transferred from Milwaukee to the Talladega Test Facility in Alabama, where he tested current and future products. Troy has now transfered to the Florida Evaluation Center in Naples Florida where he continues to test future product for Harley-Davidson Motor Company.

Roger served four years with the U.S. Navy in Norfolk, Virginia as a Machinist Mate aboard the FF-1097 USS Moinester. In 1992, Roger returned home to Danville, Illinois and utilized his military education by working for his father as the Service Foreman in the business. His philosophies have allowed him to be highly respected by customers and individuals within the professional racing community. His Gutterridge Harley-Davidson box truck is a fixture that is known across the country due to his sponsorship of the 883 premier support class on the AMA Grand National Circuit. Roger married Linnette, who is now employed as the Promotions and Event Manager for the dealership. Roger has a son named Tyler, and he and Linnette have had two children name Elizabeth Grace and Jacob Rayce. His children can be seen at the dealership on a regular basis being raised, as he was, around motorcycles.

In November 1998, a new 7,600 square foot addition was added to the existing building and opened for retail in June of 1999. This is the current structure that you see when visiting Gutterridge Harley-Davidson/Buell. The new addition included a state-of-the-art service area complete with full dyno sound room and showroom for clothing, collectibles, and chrome accessories. On August 11, 2001, the local Aldi grocery store and parking lot adjacent to the current dealership was purchased. This gives us space for motorcycle events. Some service operations and storage are housed within this structure.

On June 28, 1994, Jacob and Ruth Gutterridge were killed in an automobile accident in Indiana. Their funeral included a motorcycle procession that consumed most of Vermilion Street leading to their grave site. There were motorcycles and people from as far away as South Carolina, Alabama, and Seattle, Washington. Jake and Ruth rode with many people throughout their days creating a legend. This legend will live on in the Gutterridge Harley-Davidson Family Dealership.