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Cynthia C. Bailey

Cynthia C. Bailey

Caruth
March 17, 2026

Cynthia Callaway Bailey, a beloved wife, mother, grandmother, sister, counselor and friend, lived a life defined by compassion, adventure, and unwavering love for others.

Born on March 27, 1947, in Hot Springs, Arkansas, Cynthia was the first child of Stell and Jodie Jean Callaway. When her parents welcomed a second daughter, they gave Cynthia the special honor of choosing her sister's name. With a child's certainty and pride, she chose Polly Ann, beginning a lifelong bond between the two sisters.

Cynthia grew up and attended school in Arkadelphia, Arkansas, a town she loved so much she chose to remain there for college at Henderson State University. It was at Henderson that she met the love of her life, Paul Bailey. Paul, a Henderson State football player, quite literally swept Cynthia off her feet when he picked her up in the Henderson cafeteria--an unforgettable beginning to a love story that would last a lifetime. The two married while still students, beginning a partnership full of laughter, devotion, and shared adventures.

After graduation, Paul joined the United States Army. Their journey took them overseas to Germany and Italy before returning to the United States, where they welcomed their daughter, Allison. When Paul attended flight school and later served in Vietnam, Cynthia remained in Arkansas.

The family later moved to Fort Knox, Kentucky, where their son John was born. Another move brought them to Fort Rucker, Alabama, where Cynthia pursued her passion for helping others by earning a master's degree in counseling. From there, the family continued their military travels to Fort Hood, Texas, where Cynthia worked as an elementary school counselor.

Their adventures abroad continued with assignments in Ankara, Turkey, and Mannheim, Germany, experiences that helped shape Cynthia's lifelong love of travel and cultures. Eventually the family returned to the United States and settled in Texas, where they spent many wonderful years. During that time, Cynthia worked both as a school counselor and a school psychologist.

Later, Cynthia and Paul returned home to Hot Springs, Arkansas, to help care for their parents. There, Cynthia continued her work with the Lakeside School District as a counselor and school psychologist, serving students and families with warmth, wisdom, and a generous heart.

In time, Cynthia was diagnosed with Parkinson's disease, but true to her nature, she faced the challenge with determination. She became an enthusiastic participant in Rock Steady Boxing, finding strength in the community and continuing to inspire others with courage and perseverance.

Cynthia also embraced life's joys with remarkable enthusiasm. She loved traveling with Paul and her dear friends, exploring Europe, Southeast Asia, and Australia. Just as meaningful to her were the adventures she shared with her children and grandchildren--trips to Alaska, Hawaii, and the Caribbean that created memories her family will treasure forever.

A lifelong animal lover, Cynthia was passionate about helping animals in need. She devoted time to Paws and Claws and joyfully rescued her two beloved dogs, Tanner and Lily. At the family farm, she also helped care for numerous other dogs who found safety and love through her kindness.

Perhaps Cynthia's greatest gift was her compassion for people. She never met a child--or an adult--in need that she did not try to help. Whether providing food, clothing, encouragement, or simply love and understanding, Cynthia quietly made the world brighter for everyone she encountered. Those who knew her agree that the world was a much better place because Cynthia Bailey was in it.

Cynthia was preceded in death by her beloved husband of fifty years, Paul Bailey. Their family takes comfort in imagining the two of them reunited, walking their dogs together in heaven.

She is survived by her daughter and son-in-law, Allison and Brad Dierlam, and their children, Carter and Ella; her son and daughter-in-law, John and Tess Bailey, and their children, Victorine and Justice; her sister, Polly Ferguson; her nieces Bonnie and Katherine; and her great-nieces, Kinley, Aida and Amelia.

Cynthia's family celebrates her extraordinary life, her generous spirit, and the immeasurable love she gave so freely. Her legacy lives on in the countless lives she touched, the family she adored, and the kindness she spread wherever she went.

Visitation will be from 10-11 a.m., with a celebration of Cynthia's life to follow at 11 a.m., on Thursday, March 19, at Caruth-Hale Funeral Home.

Online condolences athttp://www.caruth-hale.com.

Service Information

Visitation will be from 10-11 a.m., with a celebration of Cynthia's life to follow at 11 a.m., on Thursday, March 19, at Caruth-Hale Funeral Home.

Arrangements by: Hale Funeral Home

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