While still a very young man, Cass Simpson, left Portland because of his health and went to the Condon, Oregon area where he worked in the sheep business for local sheep men. He later joined into the sheep business with Giles Parman, who later would become his father-in-law. Parman and Simpson ran their sheep in the upper Hay Creek and Snipton Canyon area, trailing them to summer range on the Strawberry Mountains, south of John Day and Prairie City.

In about 1902, Cass Andrew Simpson and Sarah Helena Parman were married. They spent the first summer of their married life tending sheep on Strawberry Mountain. Later they owned and operated a steam laundry and a feed and fuel business in Condon, but in 1905 they traded these business for a ranch in Kahler Basin, just eight miles north of Spray in Wheeler County, where they lived until 1935. In 1981, the ranch was owned by former governor Robert Straub.

To this union were born nine children.
Gilbert married Ada Anderson of Spray;
Kenneth married Barbara Quint of Condon;
Ted married Rose Straube of Waterman Flat;
Jack married Nova Hedin of Portland;
Mildred married Charles Whyte of Condon;
Virginia married Fred Low of Spray;
Rebecca married Willard Navarre of Portland;
Alice married Andy Bellomo of Pendleton.
Margery June died at age 10, in Portland, at the home of Ruth Simpson Haley, Cass's sister.

At the time these early pioneers came to Gilliam County, there was no town of Condon, but a good spring called "Summit Spring" which was vital to this area and caused people to settle here, forming the town.

The water from the spring was piped into a large trough which not only served the town people, but was used to water freight teams as they passed through this area hauling from Fossil to Mayville to Condon and Arlington. (Written by Alice Simpson Bellomo and Gilbert Simpson, 1981)

Home in 1910: Condon, Gilliam, OR (Apr 15)
Cass A Simpson, 35, NE, Married 8 years, Proprietor Steam Laundry
Ellen Simpson, 34, KS, Children 4 total & 4 living
Gilbert Simpson, 5, OR
Kenmon Simpson, 3, OR
Theodore Simpson, 2, OR
Byron Simpson, 4/12th, OR

WWI Draft Registration: 12 Sep 1918
Name: Simpson, Cass Andrew
Birth Date: 29 Mar 1875
Age: 43
Residence: Winlock, Wheeler, OR
Nearest Relative: Sadie Helen Simpson
Occupation: Farmer Stockraiser
Medium Height, Slender Build, Blue Eyes & Black Hair

Home in 1920, Spray, Wheeler, OR (Jan 1)
Cass A Simpson, 44, NE, Owns farm
Helen Simpson, 44, KS
Gilbert Simpson, 14, OR
Kenneth Simpson, 12, OR
Teddy Simpson, 11, OR
Jack Simpson, 10, OR
Mildred Simpson, 7, OR
Virginia Simpson, 6, OR
Rebecca Simpson, 3 & 1/12th, OR
Alice Simpson, 1 & 1/12th, OR

Home in 1930: Spray, Wheeler, OR (Apr 1)
Cass A Simpson, 55, NE, Age first married 26, Stock Farmer
Helen S Simpson, 54, KS, Age first married 25
Gilbert P Simpson, 35, OR
Kenneth P Simpson, 23, OR
Theodore L Simpson, 21, OR
Jack R Simpson, 19, OR
Mildred L Simpson, 17, OR
Virginia R Simpson, 16, OR
Rebecca E Simpson, 13, OR
Alice H Simpson, 12, OR
June M Simpson, 9, OR