Dennis C. Olson

Dennis C. Olson was always a man with a joke to tell and a smile to give.

He was born, some might say on a bicycle, in Milwaukee, Wisconsin on January 5, 1952, to Clifford Olson and Ruthann (Brown). He earned an Associates Degree in Machining/CNC from Milwaukee Area Technical College and worked as a setup man in the heat treating department of Allen-Bradley for 37 years before retiring in 2009.

With his motto of "you rest, you rust," Dennis was an exceptional cyclist. More than 40 years ago, he helped create the inaugural route for the Bike MS: Best Dam Bike Tour and was preparing for this year's ride when he suffered a tragic bicycle accident in Palmrya. He passed away on August 23, 2025, at 73 years old.

Starting from its inception in 1978, he rode SAAGBRAW for many years. He completed several centuries, once riding the Sentinel Century on his high wheel bike, and at least one triple century. As the snazzily dressed, Milwaukee Wheelman with a camera, he regularly participated in the Great Circus Parade, the City of Festivals Parade, and Uecker's Ride for the Arts.

However, cycling and watching the Tour de France were not Dennis' only hobbies. He loved drawing, singing, wood working, and Jeopardy!, was fascinated with space and science fiction movies, and had his own photography business, Ordinary Photos. He was also the man to call if you needed to move. Not only could he pack a vehicle like none other, but it was guaranteed that, if Dennis packed a truck, nothing would break en route.

Extremely proud of his two children, Dennis traveled the country to see his daughter perform in operas and concerts. Meanwhile, he was often the only white haired man cheering on his son at his metal shows. Eager to see the wider world, he explored the Caribbean multiple times and enjoyed a mini European tour in 2017.

Dennis was a man of deep faith who sang bass in his church choir for decades. His beautiful voice, humor, kindness, and positivity made him an unforgettable presence. He always strove to see the best in everyone he knew. He shared his generous spirit, along with his favorite joke, with friends and strangers alike. And his supply of entertaining t-shirts seemingly never ended. His zest for life was unwavering. He truly lived each day as a gift. 

Dennis is survived by his beloved wife Elaine Stratton and his children from his first marriage, Ryan D. Olson (Jennifer) and Rebecca L. Sjöwall (Marcus), his grandchildren (Jussi, Thorin) as well as bonus grandchildren (Damien, Gabriel, Dana, Mick, Amy, Shane, Johana), his siblings (Linda, Dotti, Lori, Mark, Scott), and many nieces, nephews, bonus family, and friends.

A service of witness to the resurrection will be held at Highview Presbyterian Church at 11:30am on Saturday, September 6, 2025. Visitation with the family will be held from 10:00am. Lunch will be served in the Fellowship Hall following the service. The address is S50 W33042 Town Road GE, Dousman, WI 53118.

In lieu of flowers, the family requests that donations in his name be made to the following organizations that were extremely important to Dennis:

Highview Presbyterian Church https://www.highviewepc.org/

Lad Lake https://www.ladlake.org/

Bike MS: Best Dam Bike Tour https://events.nationalmssociety.org/participants/743083/donate