Dennis Wayne Caldwell

Dennis Wayne Caldwell

Dennis Wayne Caldwell, 86, of Black River Falls, formerly of Platteville, passed away Tuesday, Dec. 23, 2025, at his home surrounded by his family.

He was born Sept. 24, 1939, in Beloit, WI, to Kenneth and Dorothy (Case) Caldwell. As a child, he was an avid ski jumper and even braved the large ski jump in Beloit. He graduated from Beloit High School and went on to serve his country in the US Air Force. The primary airplane Denny served on in the Air Force was a C-124 Globemaster, commonly known as “Old Shaky.” Dennis continued his love of flying throughout his life. He enjoyed flying his own plane, a Tri-Pacer, tail number “N8807D” and even tried sky diving in his 70s. 

Dennis was married to the love of his life, Carol, for 54 years. Together they raised seven children. He spent most of his career as the building and grounds supervisor for Platteville Public Schools. He also ran a shoe repair shop out of his house in his spare time. Even into his retirement, he maintained his hard work ethic, taking various grounds maintenance jobs.

Denny served as president of the Platteville Airport Commission at one time. He enjoyed entertaining with his pig roaster for holiday weekends and graduation parties and even smoked meat for the Chicago Bears picnic in Platteville. He dedicated significant time and effort into improving his home and land and was always known for coming up with the next project to keep him busy.  “The man who is always busy is at rest” would describe Denny’s outlook on life.

Dennis will be remembered for his great sense of humor and love for all his family. He greatly enjoyed spending time with his grandchildren.

He will be dearly missed by his wife, Carol Caldwell; seven children, Suzann (Mark) Wimmer, Tom (Sue) Caldwell, Sandy (Elmer Benedetti), Jody (Kari) Nichols, Brad Nichols, Denise (Kevin) Roddick and Tricia (Shawn) Reif; 12 grandchildren; five great-grandchildren; and many other relatives and friends. 

He was preceded in death by his parents and furry best friend, Ellie. 

The family would like to thank St. Croix Hospice for their excellent support and care of Dennis.

Private family services will be held at a later date.

Torgerson Funeral Home in Black River Falls is assisting the family with arrangements. Online condolences may be shared at www.torgersonfh.com.