Pioneer Rancher of the Upper Crooked River
By Steve Lent, Crook County Historian
Thomas Jefferson “Jeff” Stewart was born on August 10, 1868, in Corvallis, Oregon. Just a few months later, his parents, John and Mariah Hobbs Stewart, moved the family south to Days Creek in Douglas County. They remained there until 1883, when they set their sights eastward and relocated to the high desert of Central Oregon. Settling near the confluence of the north and south forks of the Crooked River—between present-day Post and Paulina—they established a ranch that would become the center of their lives for years to come.
The Stewarts worked the land and raised cattle along the fertile riverbanks until 1899, when John and Mariah returned to Douglas County with their younger children. Jeff, however, stayed behind to run the ranch. In 1902, his brothers Ed and Al joined him. Together, the three transformed the ranch into a successful cattle operation. Despite being paralyzed from the waist down, Ed ran the local telephone switchboard—linking Post to Paulina—and remained an active part of the team.
The Stewart ranch was ideally placed near a dependable water source, and Jeff became one of the region’s most prominent cattlemen. He frequently joined neighboring ranchers on long cattle drives to the railhead in Ontario, a grueling but vital journey for the business.
More than just a working ranch, the Stewart homestead became a familiar stop for travelers making their way between the Upper Country and Prineville. Jeff lived in the large, two-story house built by his parents and remained there for the rest of his life. He never married, devoting his years instead to the land and the life he’d built on it.
Jeff was also active in the International Order of Odd Fellows in Prineville, reflecting his strong ties to the community. In mid-September of 1941, he suffered a heart attack and was rushed to Stevens Hospital in Prineville, where he died on September 17 at the age of 73. He was buried at the I.O.O.F. Cemetery, now part of Juniper Haven Cemetery in Prineville.
After his death, Ed and Al sold the ranch. In time, the property became the headquarters for the Les Schwab Ranch, carrying forward the legacy of a pioneer family that helped shape the Upper Crooked River region.