Harold J. Ryan
Harold “Harry” J. Ryan, 83, of Arcadia, passed away Wednesday, April 8, 2026, at St. Anne Extended Healthcare, Winona, MN.
Harold was born July 19, 1942, to John & Linda (Weltzien) Ryan. He married “the girl from the valley”, Mary Boberg, February 1, 1964, at Our Lady of Perpetual Help Catholic Church in Arcadia.
Harold worked the family farm in Glencoe until his marriage. He then started his lifelong career of trucking. He began with Wnuk Trucking, picking up milk from local farmers before moving onto semi driving with AG Co-op Creamery hauling milk and delivering cheese. After AG closed, he transported boxes of chicken for Arcadia Fryers. Before electronic logging, he put in very long days and never said no when the dispatcher called for him to put on more miles. One day he told his wife he “went around the world” as he had driven a very long distance, in the shape of a circle. After driving for 41 years, he declared “it’s not fun anymore” and retired at the age of 61.
Harold enjoyed his retirement, catching up with lifelong friends, spending time with family and enjoying being a big part of Mary’s at-home day care. Mowing his lawn and blowing snow with his John Deere garden tractors were his hobbies. You could always count on him to go up and down Wilson Avenue to help neighbors clear their driveways.
Harold’s greatest pastime was spending time with his daughters, granddaughters, and great-granddaughters. Whether it was being their mechanic, slipping some money to the granddaughters when grandma wasn’t looking, putting on a fireworks show on Wilson Avenue or making sure everyone received a Christmas gift specifically from him, he was always there for “his girls”.
We miss him every day. You knew he was up to something when his beautiful blue eyes were sparkling, enjoying a good meal at a restaurant with his family, taking backroads with his daughters and sharing all the stories — all the little moments and traditions his wife and three generations of girls hold dear.
Harold is survived by his wife, Mary; children: Janet Rumpel (Randy Scharlau) & Rita (Dan) Fliehr; granddaughters: Natasha Schank, Cheylene Schank (Matt Duffy), Sydney (Kurt) Schwieters; great granddaughters: Malaina Tullius, Noa Schwieters, Elowyn Duffy-Schank; sisters-in-law: Frances Ryan, Darlene Boberg, Rosie (Gene) Comero, Joyce Sobotta (LeRoy Drinkman); brother-in-law, Alvin (Carol) Boberg; and many nieces and nephews.
He was preceded in death by his parents; brother, Kenneth; and sister, Bonnie (Albert) Tamke; sister-in-law, Theresa Boberg; brother-in-law, Jim Boberg; great grandson, Linden Duffy-Schank; nephews: Duane Tamke and Andy Scoles; and a great nephew, Dustin Boberg.
A Memorial Mass of Christian Burial will be held Friday, May 1, 2026, at 11:00 a.m., at Holy Family Catholic Church in Arcadia, with Father Kyle Laylan celebrating the mass. Visitation and a light lunch will follow the mass until 3:00 p.m., at the Arcadia Country Club.
The family appreciates your expressions of sympathy, but respectfully declines gifts of flowers, and instead would appreciate memorials being directed to the Arcadia Ambulance Service and Arcadia Fire Department. We appreciate all the care and assistance they provided throughout the years.
Harold’s family would like to extend their deepest appreciation to St. Croix Hospice of WI & MN, and Benedictine Living-St. Anne 2nd floor staff. Special thanks to Fr. Kyle Laylan and St. Anne’s Pastors for their many visits.
Chippewa Valley Cremation Services – Celebration of Life Center in Altoona, is serving the family. Online condolences or memories may be left for Harold’s family at www.chippewavalleycremation.com.
