Shirley Cress

Shirley Alice Cress lived 94 years filled with family, faith, hard work, laughter, adventure, and an extraordinary amount of caring for other people. She passed away on August 27, 2026.

Born January 11, 1932, on Bennett Road in the Town of Worcester, Wisconsin, Shirley was the daughter of Henry and Ruby Olson. She spent part of her early childhood living with her grandparents, and then with her parents in Ogema. She attended Ogema Grade School and later Prentice and Phillips High Schools.

On July 23, 1949, Shirley married Tom Cress, beginning a marriage and partnership that would take them from northern Wisconsin to Alaska and eventually back home again. Together they raised four children—Marianne, Sherilynn, Timothy and Michael—and built a family that grew to include eight grandchildren, 13 great-grandchildren and four great-great-grandchildren.

Shirley and Tom left Phillips in 1969 and spent nearly a decade in the hotel business in Fairbanks. Even their first attempt at “retirement” didn’t last long. During the winters, they worked for the State of Alaska as cooks for highway crews responsible for keeping Thompson Pass near Valdez open through over 50 feet of snow per year. At age 55, when many people are beginning to think about slowing down, Shirley attended Prince William Sound College in Valdez and later worked as an assistant to the Director of Instruction.

Eventually, Shirley and Tom really did retire. They traveled throughout the country in their fifth-wheel trailer, visiting 49 of the 50 states before returning to Phillips. They continued traveling to visit their children and grandchildren in Ohio, West Virginia and North Carolina.

Family and faith were at the center of Shirley’s life. She was a member and tireless volunteer at the United Methodist Church in Phillips for more than 70 years. Even during the final four years of her life, when she could no longer physically attend services, Sunday still meant “going to church”—she simply watched the service by livestream on her iPad. A special thank you to Julie Olson for her love and care over many years.

Shirley’s faith was reflected in the way she treated people. Throughout her life, she cared for parents, grandparents, siblings, friends and other family members. She volunteered for years at the nursing home alongside her very special niece, Carolyn Liebelt, and was a devoted caregiver to Tom, first at home and later during his time in the nursing home.

There may have been no better evidence of Shirley’s kindness than the way she remembered people. She kept track of birthdays and anniversaries and was an inveterate sender of cards. Birthday, anniversary, get-well and sympathy cards—and an enormous list of Christmas cards—went out year after year. If someone was celebrating, was sick, or had lost somebody they loved, Shirley remembered. Even in her final three days, she still found time to send several birthday and sympathy cards.

Shirley was proud of her Scandinavian heritage and had an extraordinary knowledge of both the Olson and Cress family histories. With the help of family members and others who shared her interest in genealogy, she preserved family stories and connections reaching back generations, including the family’s roots in Sweden.

Most of all, Shirley loved her family and took enormous pride in watching the family she and Tom began continue to grow. She also loved to laugh, and her sense of humor remained intact until the very end. Mike can attest to the fact that she confirmed he was the favorite child during her final days. The day before she died, she told Mike she was certain she was going to heaven…but jokingly said she wasn’t certain about him. Mike told her she might need to recruit some help with that once she got there.

Shirley is survived by her son, Mike (Anne) Cress; her sister, Carol (Roger) Hlavacka; eight grandchildren; 13 great-grandchildren; four great-great-grandchildren; her daughter-in-law Michelle Cress and son-in-law Bobby Caldwell; her special niece Carolyn Liebelt; and many other nieces, nephews, relatives and dear friends.

Her grandchildren are Michael (Kathleen) Cress, Elizabeth Cress and Katie (Alec) Cress, children of Mike and Anne; Jessi Masciotra and Zac (Dominique) Cress, children of Tim; Heather Lepka and Christopher Caldwell, children of Sheri; and Jaime (Dennis) Burns, daughter of Marianne. Her great-grandchildren are Cora, Charlotte and Turner Cress; Alexis and Finnegan Marshall; Emery Masciotra; Rhemni and Annabelle Cress; Colton Caldwell; Olivia Caldwell; Jacob (Michaela) Lepka; Tyler (Yarilynn) Caldwell; and Megan Caldwell. Her great-great-grandchildren are Rhianna, Makenna, Adalyn and Ava.

Shirley was preceded in death by her husband, Tom; three of their four children, Marianne Deitz and her husband, Bruce, Sheri Caldwell and Tim Cress; her parents, Henry and Ruby Olson; her sisters, Phyliss (Ray) Johnson and Dorothy (Harold) Popple; her brother, Jerry Olson; and other beloved family members and friends who went before her.

In her final days, Shirley spoke about looking forward to seeing Tom, Marianne, Sheri and Tim again. Her faith gave her comfort and confidence about what came next, and she promised Mike she would do her best to get him in.

Shirley spent a lifetime taking care of other people, so it is especially meaningful to her family that others had the opportunity to take care of her during the final 3½ years of her life. Our family will be forever grateful to the extraordinary staff at Park Manor, who didn’t simply care for Shirley—they came to know her, love her and watch over her. A special thank you goes to her amazing CNA, Diane, and her dear friend Bertie.

Shirley gave far more than she ever expected to receive. She showed up for people. She remembered them. She took care of them. And she loved her family deeply. After 94 years of doing all of that, Shirley has earned her rest. Rest in peace, Mom. We love you, we will miss you more than words can say, and we will meet again.

A funeral service will be held October 17 at 11:00 a.m. at the United Methodist Church in Phillips, followed by lunch. In lieu of flowers, donations may be made to the United Methodist Church, 115 Center Ave., Phillips, WI 54555.