Constance "Connie" Jones Gregory

Gregory, Constance “Connie” Jones, 87, of South Boston, Virginia, passed away on December 2, 2025.  She was born in Caretta, West Virginia, on March 30, 1938, to William Gratton Jones and Roma Sparks Jones. Connie was married for 66 years to her beloved husband, John Richard Gregory, who precedes her in death.

She is survived by her son Richard “Rick” (Deborah); four grandchildren, John (Forrest), Erin (Jim), Colleen, and Lauren (Tyler); and five great-grandchildren, Hagan, Campbell, Roma, McKennon, and Kenley. Additional survivors include her brother Theodore “Ted” (Brenda); sister Iris “Sandy”; and daughter-in-law Sonja, widow of her beloved son Michael “Mike,” who also precedes her in death. In addition to Mike, she was preceded in death by her siblings, William “Bill,” Sue, Robert “Bob,” George, and Anthony “Tony.” Her beloved grandson, Robert “Warren,” also preceded her in death.

Born the daughter of a coal miner, Connie spent her early years in the Appalachian Mountains where she developed a deep love of nature that she carried throughout her life. She moved to Rocky Gap, Virginia, in her teens, and it was there that she met Richard, the quiet, steady presence who would become her lifelong partner. 

Connie married at 18, became a mother at 20, and grew into a woman defined by fierce devotion, unstoppable determination, and an unshakeable commitment to family. In 1967, she became one of the first women in South Boston to own and operate her own business, Gregory’s Florist. The newspaper article that ran about the opening described her as “a young South Boston housewife with too much energy.” In truth, Gregory’s Florist was born out of a desire to bring people genuine joy and comfort.  After receiving flowers during a hospital stay and watching them quickly wilt, Connie decided she wanted to create arrangements that would last longer and fill up rooms with vibrancy. Connie built a thriving business during a time when few women were encouraged to do so, and for nearly six decades, her shop has been a cherished fixture of the community and continues today under the care of her daughter-in-law Sonja and granddaughter Lauren.

Connie believed deeply in supporting her town and devoted countless hours to serving on the Board of the South Boston Chamber of Commerce, participating in the Cotillion Club, and celebrating life with the Red Hatters Society.

As one of the eldest of her siblings, Connie was a natural caregiver. Over the years, her home became a refuge where younger brothers and sisters were welcomed, fed, and loved. She carried that same fierce, vibrant love into her role as a grandmother. Her grandchildren were “her babies,” and she delighted in spoiling them. Later in life, she could often be found with her sister-in-law, Brenda, cruising around town Thelma-and-Lousie-style hunting for the grandchildren’s Christmas gifts.  Connie was the matriarch of her family—bold, colorful, protective, and endlessly loving. She lived life out loud, a fierce protector when she needed to be and a soft place to land when it mattered most. Her legacy is one of generosity, grit, beauty, and deep devotion, carried forward by the family she cherished and the community she helped shape.

The Gregory family wishes to thank the staff of Sentara Halifax Regional Hospital and First Care Hospice for their exceptional care as well as Connie’s devoted sitters, Joyce King, Joyce Barker, and Sandra Wilborn.

A service will be held at Powell Funeral Home in South Boston, Virginia, on Monday, December 8th, 2025, at 11:00 am. The family will receive friends one hour prior to the service at Powell Funeral Home.

Online condolences may be directed to www.powellfuneralinc.com.

Arrangements are by: Powell Funeral Home, 1603 Wilborn Ave., South Boston, VA, 24592.