Cover photo for Daisy Winslow's Obituary
Daisy Winslow Profile Photo
1926 Daisy 2023

Daisy Winslow

September 26, 1926 — February 4, 2023

Daisy Caldwell Winslow, nee Roberts, the daughter of Henry and Pearl Roberts, passed away peacefully on February 4, 2023, at her home in Spartanburg, SC. She was 96.

Born and raised in Columbus, WI, Daisy graduated from the University of Wisconsin with a degree in Economics. She married a childhood friend, Hugh Caldwell, Jr. in 1949. After a short career with Wisconsin Power and Light in Madison, they returned to Columbus to raise their family.

Her husband’s career took the family to Hudson, OH and Orchard Park, NY before moving to western South Carolina in 1976. Along with her husband, she opened Carolina World Travel in Tryon, NC, where she worked for several years. After selling the business, Hugh and Daisy searched for a retirement community and settled at Summit Hills in Spartanburg, where she has lived for the last 18 years.

Daisy was an active community volunteer, and she especially loved singing. She was active in multiple church and community choirs. An avid sports fan, Daisy loved watching the Atlanta Braves and Green Bay Packers.

After her husband Hugh passed away in 2007, she found love again and married Don “Bear” Winslow in 2010.  She was welcomed into Don’s large, close-knit family, and they loved traveling and staying connected to family until his death in 2022.

Daisy is preceded in death by her husbands, Hugh Caldwell, Jr. and Donald Winslow and by her sister Doris Roberts Harvey of Palo Alto, CA. She is survived by sons Hugh “Mac” (Allison) Caldwell of Boulder, CO and Richard (Roxanne) Caldwell of Shelby, NC; daughters Jean (Tony) Passarello of Atlanta, GA and Catherine Ferretti of Sarasota, FL; six grandchildren; six great-grandchildren and multiple stepchildren, step-grandchildren and step-greatgrandchildren.

A graveside service for family will be held in Columbus, WI at a future date.

In lieu of flowers, memorials may be made to Mobile Meals Service, P.O. Box 461, Spartanburg, SC 29304, online at

Floyd’s North Church Street Chapel

To order memorial trees or send flowers to the family in memory of Daisy Winslow, please visit our flower store.


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