Ann Weaver Bailey

ROCKY MOUNT – Ann Weaver Bailey, lovingly known to all as “Mama Ann,” passed away peacefully on Monday, February 16, 2026.

Ann was born in Nash County, NC on June 21, 1925.  After losing both of her parents by the age of eight, Ann grew up at Oxford Orphanage.  Despite those early hardships, her life became a powerful testimony of perseverance, joy, and unwavering determination and faith.

In 1944, Ann moved back to Rocky Mount where she met and married the love of her life, Clyde Bailey Sr.  Together, they founded Bailey’s Fine Jewelry in 1948, building not only a successful business, but a lasting legacy rooted in love, family, and hard work.  When Clyde passed away, Ann found herself a widow with two small children and a business to run — and she rose to the challenge with remarkable courage and strength.  Her motto, “Keep on keepin’ on,” was more than a saying, it was the way she lived her life.

Mama Ann was young at heart, the life of the party, and a source of joy wherever she went.  She truly lived life to the fullest.  After retiring, she cherished traveling and spending time with her grandchildren, and later, her great-grandchildren, who brought her immeasurable joy.

She always said her middle name was “Go.”  She was ready for anything — whether it was going out to breakfast, playing cards, sharing meals with friends and family, or heading off on a trip.  If there was living to be done, Mama Ann was ready.

She is survived by her son, Clyde Bailey Jr. (Jane); her daughter, Cindy Bailey; her grandchildren, Morgan Bailey Morgan (Doug), Trey Bailey (Marci), Gavin Stone, and Anne-Hunter Stone Stroud (Stuart); and her great-grandchildren, Bishop Morgan, Weatherly Bailey, Ford Bailey, and Windsor Bailey.

A Funeral Service to celebrate Ann’s life will be held on Friday, February 20, 2026, at 1:00 PM at Edgemont Baptist Church, 1622 West Mount Drive, Rocky Mount, NC  27803 with Rev. Mike Edwards and Rev. Thayer Stamper officiating.  The family will receive friends and relatives on Thursday, February 19, 2026 from 5:00 PM to 7:00 PM at Wheeler & Woodlief Funeral Home.

A private family burial will take place at Pineview Cemetery.

Flowers are welcome or memorials may be made in Ann’s memory to Edgemont Baptist Church, P.O. Box 7293, Rocky Mount, NC  27803.

Arrangements entrusted to Wheeler & Woodlief Funeral Home & Cremation Services, 1130 N. Winstead Avenue, Rocky Mount, NC 27804.  You may share memories and condolences with the family by visiting www.wheelerwoodlief.com.