The Whitaker Ranch was established by Dugald R. and John Whitaker. Raised in
the region around Shropshire, England, the two brothers left their green and rain-kissed lands for the high and windy plains of Wyoming in 1892. In 1895, the brothers bought two separate ranches on Horse Creek north and west of Cheyenne and tried their hand in the cattle business. Dugald became a widely respected cattleman was president of the Wyoming Stock Growers Association for three terms.

Dugald met and married Elizabeth Smith of Cheyenne, daughter of the nation's first county librarian here in Cheyenne. Together they raised two daughters, Elizabeth and Mary. Elizabeth worked alongside her mother and father. While doing so, she married attorney Robert Caldwell of Cheyenne. Both took on the responsibility of keeping the family ranch going. It was Elizabeth who first got the Whitaker family involved with Cheyenne Frontier Days. A good friend of Margaret Boice, Elizabeth helped run a branding float operated by the"Cow Belles:' Along with Margaret Boice, Mary Carpenter, Ann Dinneen and others, Elizabeth helped found the W-HEELS in 1925 and continued to help with the parades through the 1940s. Her husband, Robert, was also involved with the parades, being the principal driver of the Dr. Crook cart which still rolls in the parade today. By circumstance of their parents being so involved with the parades, the Caldwell's two daughters, also named Elizabeth and Mary, came to participate in CFD as well. Mary recalls: "One day I rode through the parade with my father in the Dr. Crook carriage, and they put a sign on it - 'Up for Adoption: I cried all the way through the parade. I thought they were going to put me up for adoption:' - Wyoming Tribune Eagle, May 29, 2005. They didn't and Mary and her sister continued to be involved for many years.

In 1959, while she was away at college, Mary received a call that she had been selected as the 1960 Lady-in-Waiting. She became Miss Frontier in 1961 . Two years later, she married Ed Weppner who had also been deeply involved in CFD since he was a young man. From the age of seventeen, Ed had been responsible for picking up carriages from people's homes for use in the parade. He also organized the trucks to haul the Dazee Bristol floats in the parades and served as an outrider. The involvement of the Weppners continues today with Mary volunteering for the CFD Western Art Show and Sale and as a "Textile Lady" working with parade costumes and other garments at the Old West Museum, which she helped found in 1978. She became a W-HEEL like her mother in 1979. Ed served on the CFD racing committee for several years and was instrumental in running the Chuck Wagon Races in the 1980s and 1990s. In 1983 he became the Contract Acts Chairman, serving through 1986. During that time, he hired Reba McIntire to perform at CFD for the first time and brought many other top acts. He became a HEEL in 1973 and has been the manager of the Whitaker Ranch since 1976. The three Weppner children also became involved in CFD with Rob working with Contract Acts and the horse races in the arena for twenty-two years. He too became a HEEL in 2001 .
Ginny Weppner served as a Dandy from 1980 to 1983 as did Tricia from 1989 to 1991. Tricia's involvement followed in her mother's footsteps when she was picked to be Lady-In-Waiting in 1993, and Miss Frontier in 1994.
Mary's sister Beth continued working with the parades. She enjoyed riding horses in the parade both on a side saddle and with a split skirt. She served as an outrider and assisted in not only coordinating the carriages and their use in the parades, but also lent a hand in their preservation as well. To thank the drivers, she took on the responsibility of running the annual luncheon in their honor. In 1967, Pete McNiff married into the family and brought a great deal of dedication to the event as well. He worked on the Parade and Indian Committees and in 1981 was named Publicity Chairman. One of his favorite activities during the celebration was to drive the Whitaker family's maroon Jeepster in the parade. This vehicle had the singular honor of driving Miss Wyoming in the parades. While not driving the car, Pete announced the parades and has recently been seen as the Master of Ceremonies for the Coronation Ball. The McNiff children have also followed their parents into CFD. John drives the Jeepster while Wann served as a Dandy from 1993 to 1995 and rides in the parade's sidesaddle and split skirt like her mother. Niffy too rode like her mother and served as a Dandy from 1986 to 1988. She also served as Miss Frontier in 1991. Her husband Chris, not to be left out, drives the Jeepster and her son gets to tag along.

Four generations of the Whitaker Ranch families have dedicated their service to Cheyenne Frontier Days and the tradition seems destined to continue. The families are all dedicated to the preservation of the ranching heritage of our region and have become familiar faces at the "Daddy of ‘Em All.'