Theodore Roosevelt, Calamity Jane, and Montana’s First Dude Ranch

The 140-year history of dude ranching has a few famous “firsts” and one of them was the O.T.O., the first dude ranch opened in Montana. It doesn’t just have a fascinating history — the ranch itself is history, because it closed decades ago and since the 1990s has been managed by the dedicated staff of the Custer Gallatin National Forest. And now, my friends at the True Ranch Collection are helping to raise funds to assist with restoration efforts. More about that later.

Dick Randall, celebrated in the 1920s brochure above, was one of the many transplants from the Midwest (Iowa, in his case, where he was born in 1866) who came West and realized that he should have been there all along. His brother had moved to Junction City, Montana in 1884 and Dick soon joined him, working at the 7 Bar 7 Ranch. The owners lost their cattle herd during the terrible winter of 1886-1887, known as The Big Die-Up, and Dick needed another line of work.

He and a friend named June Buzzell had a cabin in Gardiner, near the north entrance to Yellowstone, and they started a business trading horses and leading pack trips for hunters coming from back East and Europe. Dick married Dora Roseborough in 1892; their son Lesley, known as Gay, was born the following year, and daughter Helen came along in 1898. When the kids were little, one of the Randall’s neighbors was Calamity Jane, and Gay used to wander over to visit her because she usually had cookies on hand. Calamity’s reputation had followed her from Deadwood, and Dora Randall was not pleased when she heard that Jane had kissed her son. So, she washed out his mouth with soap.

Dick Randall was one of the best-known guides in the area and decided he needed to expand. He bought a larger cabin near Cedar Creek, about 12 miles from Gardiner. He got a good deal on the place because the men who owned it had been robbing the Yellowstone stages and things were getting too hot for them to stick around. Dick and Dora built a barn, added to their cabin, and started hosting visitors who had come to take one of Dick’s celebrated hunting trips. Theodore Roosevelt was one of them; Owen Wister, author of The Virginian, was another.

By 1912 the Randalls’ home was officially a dude ranch, and was soon named for their cattle brand: O.T.O., which was simply a collection of letters that was easy to turn into a brand and read on the side of a steer or a saddle.

Dick Randall believed in giving his dudes a true western experience, and that meant everything from riding, fishing, and camping trips to helping out with chores like branding, milking, and gardening. Dudes also took field trips to the Livingston Rodeo and got to ride in the parade along with the famous Randalls. The O.T.O.’s main lodge had a Victrola and a piano, and the floor was always ready for folks to dance.

By the 1930s the lodge also had something else: furniture made by celebrated artist Thomas Molesworth. The O.T.O.’s architecture was classically western and rustic, with Arts & Crafts period touches and a natural hand-crafted style which was also being embraced in places like Yellowstone National Park. Molesworth, who had studied at the Chicago Art Institute, moved to Cody, Wyoming in 1931 and opened the Shoshone Furniture Company. Many of his early pieces of furniture were sold to ranches and hotels, and in 1934 he was commissioned to make chairs and tables for the O.T.O.

Courtesy Libbey Family and Custer Gallatin National Forest
Courtesy True Ranch Collection

Dick Randall was a dude ranch marketing genius. Not only did he see the value of having interior design elements that appealed to vacationing easterners, he also traveled around the country to promote the O.T.O. In 1924 a filmmaker named Charles Herbert spent time on the ranch filming the dudes in action and created a reel titled, “What the Dudes Do on a Dude Ranch.” Dick took the movie to famed Marshall Field’s in Chicago and Gimbels in Philadelphia and helped the merchandisers use the film to promote their western sportswear.

In 1928 he found out that a movie actor in Los Angeles (I could never find out which one) had commissioned a silver-mounted saddle for himself but then changed his mind about buying it. Dick was in L.A. that winter and he bought the saddle, shipping it by train to Chicago to be exhibited at stores that sold western wear. Dick also knew that dude ranching had a future, and he was one of the founders of the Dude Ranchers’ Association in 1926.

Dora Randall, like many women who co-owned or ran dude ranches, was in charge of managing the guests, the staff, and the kitchen. Next to the wrangler, probably the most important employee was the cook, and ranchers did everything they could to keep the good ones happy. This didn’t always work out, though. The O.T.O. had one cook who was surly and made watery mashed potatoes. Dora tried to explain to him how she wanted the potatoes prepared, but he quit in a huff. She then had to take over in the kitchen and serve meals to 75 dudes until she could hire a new cook.

Courtesy Libbey Family and Custer Gallatin National Forest

Dick and Dora Randall retired in 1934 and sold the O.T.O. to son Gay and former guests Chan and Mary Libbey. They ran the dude ranch through the rest of the decade and Gay wrote books and articles about the ranch. But Depression and changes in the tourism industry made it too hard to keep the ranch going, and the O.T.O. closed to dudes in 1939.

New owners included the Rocky Mountain Elk Foundation and the USDA Forest Service, with the Custer Gallatin National Forest now in charge of preserving the remaining buildings. In October of 2004, the O.T.O. ranch was placed on the National Register of Historic Places. This is good news for the ongoing efforts to save the site. And now there are even more reasons to be hopeful.

This summer, the True Ranch Collection is hosting a series of Pop-Up ranch vacations at the O.T.O. For the first time since the 1930s, dudes will be in residence again, and will enjoy what Dick and Dora Randall created over a century ago. All proceeds from the events will be donated to the Custer Gallatin National Forest to help preserve and restore the O.T.O. to its western glory.

For more information, check out their website:

If you want even more stories from the history of the O.T.O. Ranch, get a copy of Music, Saddles & Flapjacks: Dudes at the OTO Ranch by Roberta Cheney and Clyde Erskine (husband of Helen Randall). It’s a wonderful book.

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