Dorothy Ann Bailey, affectionately known as “Duff,” 90, of Bushwood, MD, formerly of Frederick, MD, passed away peacefully at her home on July 9, 2026. Born on July 29, 1935, in Frederick, MD, she was the beloved daughter of the late Viola Putman and the late Lester W. Putman.
Duff shared a loving marriage with her husband, the late Philip R. Bailey. They were married on August 2, 1958, in Frederick, MD, and spent more than 60 wonderful years together before Philip’s passing on July 17, 2019.
She leaves behind a family who will cherish her memory, including her son, Lester R. Bailey (Kaye) of Chaptico, MD; her sister, Katheryn M. Cioffi, of Frederick, MD. She is also lovingly remembered by her grandchildren, Chrissy and Kevin Jones, Jacquline and David Coetield, Jonathan and Brittany Bailey, Justin Peery, and Jill Phan, as well as her daughter-in-law, Jan Bailey. In addition to her husband, Duff was preceded in death by her son, Michael Bailey, of Fulton, MO, and her siblings, Frances R. Wilkins, Lewis H. Putman, Carol M. Benton, and Susan K. Rizzo, all of Frederick, MD; Lester O. Putman of New Mexico; Betty V. Wellen of Knoxville, TN; and Ralph R. Putman of Urbana, IL.
A proud 1953 graduate of Frederick High School, Duff went on to earn her Elementary Education degree from Towson State Teachers College in 1957. In 1973, she moved to St. Mary’s County, MD, where she devoted 30 years to shaping young lives as a teacher in the St. Mary’s County Public Schools before retiring in June 1990. She also enjoyed working alongside her family as a co-owner of DJ’s One Stop Shop.
Duff found joy in life’s simple pleasures. She loved playing cards, getting lost in a good book, spending time on the golf course, and enjoying lunches filled with laughter and friendship. Her generous spirit extended throughout the community as she volunteered with Holy Angels, St. Clements Island Museum, and the 7th District Optimist Club. Whether through her career, her volunteer work, or the kindness she showed to others, Duff made a lasting impact on the lives of many.
Her family would like to extend their heartfelt gratitude to Mary Rencher and Dorian Hernandez for the exceptional care, compassion, and friendship she provided.
The family will receive friends on Thursday, July 23, 2026, from 5:00 PM to 8:00 PM, with prayers recited at 7:00 PM, in the Mattingley-Gardiner Funeral Home, Leonardtown, MD. A Mass of Christian Burial will be celebrated on Friday, July 24, 2026, at 10:00 AM, in Holy Angels Catholic Church, Avenue, MD, with Father Timothy Baer officiating. Interment will follow at Sacred Heart Catholic Cemetery, Bushwood, MD.
Serving as pallbearers will be Jonathan Bailey, David Coetield, Nathanyal Lyon, Samantha Lyon-Carpenter, Sean McCleaf, and Walter Raley.
In lieu of flowers, donations may be made in Duff’s memory to Hospice of St. Mary’s, P.O. Box 625, Leonardtown, MD 20650.
Condolences may be made to the family at www.mgfh.com.
Arrangements provided by the Mattingley-Gardiner Funeral Home and Cremation Services, P.A., Leonardtown, MD.