Carolyn R. Bennett

April 29, 1963 - September 10, 2022
Carolyn R. Bennett

Gifts & Memorial Donations

A mom and a Systems Engineer with a passion for ballet, music, film, and tutoring Math to the non-inclined, Carolyn Ruth Bennett, or “Tenna” to her family and friends was a matriarch and a leader to all that had the privilege and honor to absorb her spirit and zest which was so beautifully unique. She was steadfast in her duty to motherhood and family throughout her 59 years.

After a powerful fight with cancer, Carolyn passed away peacefully at home on September 10, 2022, with her beloved and dedicated husband of 30 years, Anthony “Clark” Gresham at her side along with her children, dog, and cat: James Gresham, John Gresham, Matt Gresham, Lena Bennett, Roscoe, and Cloudy.

The world was blessed with Carolyn on April 29, 1963, in Norfolk, VA. Her intelligence shined throughout her school years and graduated from Bayside High School in Virginia Beach, VA in 1981 with an acceptance letter to The University of Virginia. There, she excelled and earned a B.S. in Systems Engineering where she thrived in her career as a Systems Engineer in support of the Forces Surveillance Support Center (FSSC). Carolyn helped to develop some of the most advanced radar systems on earth for the FSSC. Her finest accomplishments were not at the job as her family and friends well know.

Carolyn loved her pets! There were many during her lifetime. She loved the creative arts. Her affinity for ballet was beyond passionate. She would dance magnificently. Her devotion to film and music is unsurpassed. She piqued the interest of her friends and family with her dynamic mix tapes in the 1980s. Carolyn threw legendary parties at her mom and dad’s house that roused the neighbors but kept the guests happy with fresh blue crabs, great music, and fun. She was ever an activist for women on all fronts. Most importantly, Tenna was the matriarch of a family with four children, four siblings, and eleven nieces/nephews.

Family is where her spirit shined most brilliantly. The family was of great importance to Tenna. Her children were her treasures. Her dedication to raising her three boys and a daughter is the aspiration of every parent. Tenna cherished her children and made sure she was at home, in the end, to be with those that gave her so much happiness.

Tenna ensured the siblings and cousins remained close and attended special family events ranging from 50th anniversaries and 100 years birthdays for her maternal grandmother to the Nascar races at Richmond International Raceway. Any family member absent had to have “approved leave” from her. All jokes aside, she was the best friend to her husband, children, parents, siblings, cousins, nieces, nephews, friends, and animals. Her spirit always remains vibrant amongst her surviving family members and friends as there are so many stories to tell about her life that she will always remain alive in those that knew her.

Carolyn is survived by her husband, children, siblings, and her mother Carolyn Holsinger Bennett of Virginia Beach, VA.

She is preceded in passing by her beloved father Leonard “Boots” Bennett along with her maternal and paternal grandparents.

In honor of Carolyn’s favorite season and holiday Halloween, a Halloween Celebration of Life will be held on October 29, 2022, from 3:00 to 6:00 PM at her sister’s restaurant MoMo’s Cafe in Hampton, VA, located at 1930 Power Plant Parkway, 23666. Costumes are optional.

In lieu of flowers, memorial donations may be given to the following organizations: Cholangiocarcinoma Foundation ( and/or MD Anderson Cancer Center (

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