Wyoming’s Old Timer’s Association, the predecessor group to the Wyoming Pioneer Association, was created in 1914. Members of the organization, instrumental in helping Wyoming earn statehood, had been meeting in a less formal capacity since 1884.

Colorful characters, numbering 273 and from all across Wyoming, were in Douglas for the 1914 event. Registrants noted their name, the year they arrived in Wyoming, where they lived and their occupation. The earliest came to Wyoming in 1855 and some of the occupations were field musician, U.S. Army bullwhacker, miner, cattle manager of Cheyenne, soldiers, sheep man, cattleman, freighters, driver in C. & B. Stage Line, muleskinners, Capt. Shotgun Messenger C. & B. Stage Line, surveyor, cowpuncher and many more. The Black Hills Stage Line was also represented.

State Fair Commission President Russell Thorp oversaw the meeting and creation of the organization in 1914. According to the Wyoming State Archives, Wyoming Governor Joseph M. Carey spoke to the group from the steps of the Agriculture Hall.

Annual dues were established at a rate of one dollar. Lifetime memberships were available to those who lived in Wyoming prior to 1857 at a rate of $10. Those who became residents after July 10, 1890, the day Wyoming earned statehood, were charged $15 for their annual membership.

They continued to meet every year at the State Fair. The term ‘Old Timers’ has been defined by some as “including only those who personally had a part in bringing the Territory into Statehood.”

Beyond the forming of the Old Timers, the Wyoming State Fairgrounds was bustling with action in 1914. Hereford cattle largely filled the cattle barn and Clydesdales and Percherons were among the exhibits. According to WyomingTalesandTrails.com, H. “Captain Jim” Cook attended the fair with a group of Native Americans from Pine Ridge. Cook was known for his service as a guide on the northern plains and as manager of the WS Ranch, made famous for hiring Butch Cassidy and other members of the Wild Bunch.

On September 15, 1926, at the Princess Theater in downtown Douglas, President John Hunton called to order the first Annual meeting of the Wyoming Pioneer Association. The group was built upon the Old Timers Association. Former Wyoming Governor B.B. Brooks gave an address touching on early days and Fort Fetterman in particular. Elected officers were John Hunton, President; C.F. Mauer, Vice President; L.C. Bishop, Treasurer, and B.B. Brooks, U.C. Kimball, A.R. Merritt, and William Booker as directors.