It was started by James Norris (Dick) Randall and his wife Dora after they purchased squatters rights on a small cabin along Cedar Creek in the Absaroka Mountains.

Randall courted wealthy eastern clients (the Dudes) and by 1912 they came to the OTO to experience a "genuine" western ranch lifestyle.

The property grew to meet the needs of guests and by the 1920s included an impressive lodge (1921), cabins, barns, post office, and outbuildings.

[2] After its 1939 closing the property was sold to John Paul and Jessie Shields, who owned for more than 30 years and worked it as cattle and horse ranch.

In 2004 the site was listed on the National Register of Historic Places, and buildings are currently undergoing renovations with labor provided by volunteer groups including Passport in Time, Elderhostel and Amizade.