Columbus, WI (Stillwater, MN)

Douglas "Doug" Alan Caldwell, age 71, suddenly yet peacefully passed away in his sleep on December 26, 2025 in his Columbus home. He was born June 23, 1954 in Columbus, WI to John and Kay Caldwell. He grew up in Columbus and enjoyed summers in Green Lake, WI and Cornucopia, WI. In his later childhood, he played tight end for Columbus Cardinals Football and was a member of the undefeated championship team in 1971 before graduating in 1972. He graduated from UW-Platteville in 1978 with a degree in building construction.

In 1983, Doug married his wife Sharon and they shared 42 years together. Doug is survived by his wife Sharon, his sons Kyle Reilly (Tolkyn Kussainova), Bryce Caldwell (Alyssa Meyer) and Wyatt Caldwell (Katherine Schmidt), and siblings Bob Caldwell (Mary Caldwell), Sue Wingers, and Tom Caldwell. His family also extends internationally to foreign exchange students, including an honorary daughter from Norway, Marianne Tyren (Enda Flynn), and honorary grandsons Marcus, Oscar, and Isac.

Doug spent much of his life serving and building community. He devoted 41 years to his family business at Caldwell Lumber, originally founded in 1919. He began working there in 1978, later became an owner, and eventually closed the doors and sold the business after 100 years. Other professional roles and responsibilities included Secretary of the Columbus Water & Light Commission, Builders World Board of Directors, Mautz Paint Dealer Advisory Board, President of Columbus Chamber of Commerce, The United Way of Columbus Inc. and serving as a bank board member for over 30 years at Farmers & Merchants Union Bank, including the last two years as chairman of the board.

Beyond his professional duties, Doug always made time for what mattered most: his community. He coached youth soccer and basketball, attended countless swim meets, and remained deeply involved in his faith as a committed member of Olivet Congregational United Church of Christ and regular attendee of the United Methodist Church. He was also a former member of the Boy Scout Troop 99 Committee.

For the past 33 years, Doug was the heart and orchestrator of the Heine Bike Ride, nurturing a tradition that grew into something far greater than the ride itself. Year after year, he brought together family, friends, and familiar faces, creating a day filled with laughter, storytelling, and shared miles.The Heine Bike Ride was Doug in motion: steady and deeply rooted in community. It began in Columbus and finished 22 miles later at Heine's in Minnesota Junction for pizza, with hundreds of riders riding alongside him over the years. What Doug truly loved wasn't the route or the destination (though he would jokingly claim it was the pizza), but the togetherness.

What defined Doug most was that he lived fully and joyfully. He was an avid cyclist, craft beer connoisseur, skilled juggler, puzzle builder, daily Wordle solver, U.S. watermelon seed-spitting champion, licensed pilot, hole-in-one golfer, and enthusiastic world traveler having seen every continent except Oceania and Antarctica. He was a knowledgeable Beatles fan and Abbey Road visitor, a proud Green Bay Packers shareholder, and was thrilled to witness the Milwaukee Bucks' championship. But above all, his heart belonged to his family.

Doug was a rare human who lived with intention, led with humility, and loved without condition. He will be remembered for his warm smile, unmistakable laugh, kindness, empathy, integrity, generosity, loyalty, and remarkable work ethic. A phenomenal listener, he was steadfast and thoughtful, fully present in every moment, and had the rare gift of making everyone around him feel truly seen, valued, and supported. His quiet strength and gentle wisdom will continue to ripple through the lives of those he loved and the communities he served.

A celebration of life will be held on February 1st 2026 from 1pm–5pm at Columbus Fireman's Park Pavilion at 1049 Park Ave, Columbus, WI 53925. All are welcome to attend. We encourage guests to wear bike jerseys, Heine shirts, brewery shirts, Beatles shirts, or Wisconsin sports attire.

Memorials may be directed to the "Douglas Caldwell Memorial Fund" at Farmers and Merchants Union Bank to honor his life and values. Online contributions may be made at https://www.gofundme.com/f/r2mfj-the-douglas-caldwell-memorial-fund

We encourage you to share online condolences with Doug's family at jensenfuneralandcremation.com