Kenneth W. Olson

Kenneth Wilber Olson, 96, passed peacefully in his home on March 3, 2026, surrounded by his family. A loving husband, father, grandfather, and great-grandfather, Kenny is now reunited with his wife of nearly sixty years, Judith (Judy) Wood Olson.

Born on November 22, 1929, in Minneapolis, MN, to the late Henry G. and Ruby Johnson Olson, Kenny began his career in the Army as a Motor Pool Sgt. at Camp Rucker. After his military service, he was employed by Thermo King and travelled across the country multiple times. He would often share his knowledge of the routes he used to take and the stories that went with the trip. It was amazing to hear his perfect recollection of a route he drove over sixty-five years earlier. His over the road days ended when he was introduced to Judy by his driving partner in New Orleans, he quickly knew that he would follow her anywhere, and did – right back to Judy’s hometown of Staunton, Virginia, after marrying in 1960 and having their first son in 1961.

In Staunton, Kenny worked as the shop superintendent for Smith’s Transfer Trucking from 1962 until it closed in 1988. In addition to his work with Smith’s, he was well recognized for his expertise and skill in building race car engines. Known as the “fix-it” man, he could be found in his shop working on projects ranging from getting the neighbor’s riding mower up and going, welding car parts, or tuning the go-karts just enough to make things interesting. Many of us benefitted not only from his mechanic work, but also his green thumb, with his garden always overflowing and never a single blade of grass out of place. A member of the American Legion Post 13 for 58 years, Deacon and Trustee at Bethel Presbyterian Church, and the last original founding member of the Staunton rescue squad, Kenny dedicated countless hours towards the community, his neighbors, and his loved ones.

Kenny is survived by his children, Robert K. Olson, David M. Olson (Karen), and Bethany O. Fresh (Larry); his four grandchildren, Matthew E. Olson (Renee), Kevin G. Olson (Marie), Keely G. Fresh (Ethan), and Kenneth W. Olson; his great-grandchild, Russell Olson; his siblings, Roger Olson (Janice) and Judy Weeks, many nephews and nieces, and several special friends gained throughout the years. 

In addition to his beloved wife, Judy, he was preceded in death by a sister, Mariam Johnson.

A figure in the community and loved by all who had the privilege to know him, Kenny leaves a legacy reminding us to always travel far, care deeply, and lend the helping hand.

A memorial service celebrating Kenny’s life will be held at Bethel Presbyterian Church on March 21, 2026, at 2:00 pm, with a reception to follow.

Memorials may be made to Bethel Presbyterian Church, Memorial Fund, 563 Bethel Green Road, Staunton, VA 24401.