top of page

Donna Whipp Gravely

Donna Whipp Gravely, 60, of Middleburg, Virginia, died peacefully at home in Middleburg, Virginia on December 14, 2022, from ovarian cancer.

Donna was born on June 24, 1962, along with her twin sister Carol, in Hagerstown Maryland. The daughter of Don and Gene Whipp, she grew up in Middletown, Maryland, where she discovered ballet lessons, piano lessons at Mrs. Phillips’ home, and the joy of twirling a baton. Like so many residents of small, rural towns, one of Donna’s natural talents was forging lifelong, loyal friends.

After graduating from Middletown High School, she attended the University of Maryland, earning a bachelor’s degree in urban planning. Creativity and ingenuity were hallmarks of Donna’s college education. An architectural degree was harder than she thought, and since urban planning was popular with the football players, her degree sights became more crystal clear.

After graduation, Donna attended Hood College, and received her masters degree in business administration. She landed her first job that began a 30-year career in commercial real estate. She first worked in the Georgetown office of the Trammel Crow Company, brokering commercial office space for clients.

The industry at the time was heavily male dominated, but Donna flourished. Her colleagues loved her direct and salty command of the language that also accentuated her sense of humor, authenticity, and collaborative approach. She was naturally bright, absorbed industry knowledge quickly, used creative negotiations, and was immensely loyal to her clients. After contracts were signed, Donna frequently took both parties out for a cold Bud Light to discuss anything other than real estate.

In 1996, Donna accepted a brokerage role with Lincoln-Harris Group of Charlotte, North Carolina. Before making the move from Washington DC, Donna needed to close one other crucial deal –her relationship with Page Gravely. They had met on a blind date four years earlier that developed into a passionate friendship founded on laughter, fun, and shared friends. But it was time. Donna made an offer Page could not refuse—move with her to Charlotte and get married or say goodbye. They were married in Markham, Virginia on a cloudless fall afternoon in October 1997.

While trying to become pregnant, Donna was initially diagnosed with endometriosis, preventing her from conceiving. Donna had surgery at Duke University to correct the problem, but surgeons discovered a Stage 4 ovarian cancer tumor. After 2 1/2 years of aggressive chemotherapy. Donna was declared to be in remission in 2001.

During that time, with pregnancy no longer an option, Page and Donna travelled to St. Petersburg, and returned home with an eleven-month-old, adopted son they named “Roman.” "Roma" was the first name of Donna's beloved mother. Parenting was a gift that Page and Donna relished.

Throughout her career, Donna always enjoyed parlaying her professional relationships into lifelong personal friendships. One long-time friend recently said it best: “I can't turn the clock back but my memories with Donna are some of my best, she is so much fun...devious, curious, risky, smart, confident, pushy, stylish, creative, humorous...oh my...some of these traits I want to emulate but she had it already when she was born.”

Donna’s cancer returned in 2015, first as breast cancer, then as ovarian. She retired from commercial real estate to focus on her health. First treated at Johns Hopkins University, Donna switched to a private oncologist in New York City capable of more customized and experimental treatments.

Over the last seven years of her life, as she endured countless treatments, Donna’s greatest joy and source of strength and endurance, came from Page, Roman, and her two communities –Middleburg and Maine. They moved to Middleburg in 2004.

In 2006, Donna learned about the affordable housing services of the Windy Hill Foundation. To provide Roman, then 6, a teachable moment of community service and respecting the diversity and needs of the Middleburg community, Donna proceeded with a simple idea to bring home cooked meals to some of the Windy Hill residents, unannounced and unsolicited.

The residents’ response so moved Donna, she decided to organize an army of volunteers to cook and deliver meals to these residents on a consistent schedule. It was to be called “Friday’s Feast,” delivered every other Friday. Although commuting and working long hours at the time, Donna recruited volunteers, Windy Hill recipients, and scheduled and coordinated each Friday’s delivery.

Friday’s Feast went on for 16 years until Donna became too ill to continue. In response, the Middleburg Garden Club picked up her torch to continue serving the Windy Hill community, and to honor Donna, the volunteer service has been renamed as “Donna’s Feast.”

The Boothbay Region of Maine became a second cherished community. It began with a fluke invitation from a business friend of Page’s to vacation at their family home on a seasonal island called the Isle of Springs. The beauty of that area, and the friendships quickly developed that summer, led to 12 consecutive years of summer vacations on the same island. In 2017, Page and Donna bought a home across from the island.

Donna’s passion for gardening, natural landscapes, wildlife, hosting intimate dinner parties, and especially date nights with her girlfriends were her antidotes to her cancer battle. Her pleasures and needs were simple, and the settings and people of Middleburg and Boothbay filled her heart and soul with constant joy, love, and gratitude.

Friendships were Donna’s heartbeat. It’s no surprise as to the quality of her friendships from childhood to college, from Middleburg to Maine. Donna’s natural beauty was inside and out; she loved to laugh and make others laugh. Her loyalty and genuine care for nurturing friendships in response nurtured and sustained her through the physical and emotional tolls of so many cancer treatments.

Despite these challenges, her life remained persistently devoted to joy and love—for Page and Roman, their dogs, her twin sister Carol, her bevy of friends, her Maine and Middleburg communities, for God, and the flowers and birds within her garden. As for their many years battling an incurable disease, faith, laughter, and resiliency would remain the bedrock of that relationship.

Donna is survived by her husband, Page Gravely, and son, Roman Gravely, of Middleburg Va., and her twin sister Carol Stanfield, and her husband David, of Frederick, Maryland. She is preceded in death by her parents and brother, Brian.

Donna preferred any contributions in her honor to be donated to The Windy Hill Foundation, care of Tom Northrup, Windy Hill Foundation, P.O. Box 1593 Middleburg, VA 20118.

A funeral service will be held Saturday January 14th at 1 p.m. at Trinity Episcopal Church in Upperville, Virginia. A reception will be held immediately after the service at Donna and Page’s home in Middleburg.


bottom of page