Dale L. Olsen

Dale L Olsen, 91 passed away Tuesday, December 9, 2025 at Ciel Assisted Living Facility in Plainfield, Illinois. Dale was born on September 22, 1934 in Strum, Wisconsin to Chester and Esther (Stomprud) Olsen. He married Charlene Benson on August 5,1955 and together they enjoyed a devoted marriage of over 70 years. 

Dale was a truck driver for nearly 43 years. He surpassed 3.5 million miles and was a Teamsters union member for 35 years. In his early career, he hauled milk from local dairy farms and worked for small companies before joining Chippewa Motor Freight in 1960 where he worked 20 years. He was also a member of the Wisconsin National Guard 32nd Red Arrow Division from 1953-61. 

A job transfer with Chippewa Motor Freight brought Dale and his young family to Lisle, Illinois in 1964, where he and Charlene raised their children. In 1986, he joined Yellow Freight where he worked until his retirement in 1995. Dale and Charlene returned to Strum in 1995 where they lived until 2021. 

Dale had a deep, yet nurturing voice. He loved to sing with Charlene, and in the church choir. Dale served as Board President of the Immanuel Lutheran Church of Strum for several years. His family and friends will miss his vivid storytelling about growing up on a small dairy farm, his travels across the country, and the many memories he had of his children, grandchildren and extended family. He was a selfless man who always showed interest in the lives of those he loved. 

Dale is survived by his wife Charlene. His memory will live on with his children, Cathryn (Bruce) Hawkins, Denise (Steve) Mallory, Steven (Jean) Olsen; grandchildren, Trisha (Rob) Vega, Mike (Leslie) Mallory, Tom Kerrigan, Allyson (Jon) Oltman, Melissa (Joseph) Dassie, and Mitchell Olsen; great-grandchildren Jaxson, Lincoln, Olivia, Nikolas, Jacquelyn, Michael, Jamesyn and Brooklyn; along with numerous nieces and nephews. 

He is preceded in death by his sister, Phyllis Semingson, brother-in-law Howard Semingson; his parents, Chester and Esther; and great-granddaughter Nevada Dassie. 

A joint funeral service will be held at a later date, with Charlene by his side.