Remembering Ann MacLeod

(June 28, 1922 – April 9, 2024)

Written by Kerry Phelps Dale

Ann lived a good, long life. She was a beloved community icon. She was a faithful churchgoer with a Christian heart. She was an avid tennis player and downhill skier. She was an active member of many garden clubs. A Saratoga celebrity. A voracious reader. An accomplished writer. A loving mother and grandmother. An inspiration to all lucky enough to know her.

She was married to her best friend Sandy MacLeod, but spent much of her life a widow: Widow Ann. She was a mentor and a friend to many of the community children: Granny Annie. But to so many of her friends collected and cultivated over the years, she was simply Ann.

Of her 101 years of life, most were spent in her home state of Virginia. She was born and raised in Staunton, Virginia, and attended Mary Baldwin, where she graduated with a degree in political science. She joined the Red Cross and traveled to Europe, later returning for a job in the intelligence arm of the military in Austria. Upon returning to the U.S., she took a job with the CIA writing reports. Then she met Sandy, married, and moved to Middleburg, where she helped in his family’s horse business on her beloved Dunvegan Farm. And there she had lived ever since bringing her enthusiasm and passions to Hunt Country.

Ann cared about people, creatures, and causes. When she decided to champion a cause, she was formidable and never gave up the fight. Her tenacity and passion were simply who she was.

She attended marches in D.C., most notably Mothers Marching for Peace during the Vietnam War and more recently a march for gun control. She was an advocate for the poor and the disenfranchised and a community conduit for bringing people together. She initiated Trinity’s 30-plus-year relationship with SOME (So Others Might Eat) in Washington and faithfully served meals to hundreds every other month. As a volunteer for the organization Middleburg FISH, which provides assistance to those in need, Ann would often take a call. If she couldn’t assist through FISH channels, she would relentlessly pursue other avenues until the caller’s needs were met.

Preserving hedgerows as a safe habitat for wildlife was one of Ann’s passions. When Trinity Church started a tradition of burning Christmas trees on Twelfth Night in a bonfire, Ann revolted. Those trees were to be left at the wood’s edge to provide cover to the creatures. No more Epiphany bonfires happened again.

Ann loved her tennis, playing three games a week and participating in club tournaments until she was 99. She was old school on the court, from her all-white tennis apparel to her valued tennis etiquette. The Middleburg Tennis Club named their sportsmanship award after her. Ann set out in detail many requests for her memorial service, which were closely adhered to. “Ann never made a bad call. (Pause for hysterical laughter),” she wrote in her directives.

On the court, Ann, would not abide bad language. Once when her partner let an expletive slip out after hitting the ball into the net, Ann summoned her to the baseline. “Don’t ever cuss,” Ann chastised. “But I couldn’t help it,” her partner told her. “Next time control yourself,” she said, “…and if you must cuss, do it in Latin: awshitticus.” Ann’s personal expression of frustration was most often, “Oh, bother!” à la Winnie the Pooh.

Ann loved people and loved to talk, making her a perfect docent for Trinity Church’s annual Hunt Country Stable Tour. She was perennially the guide for the Goose Creek Stone Bridge, which she was instrumental in saving and having placed on the National Register of Historic Places. One year Ann enthusiastically flagged down a Greyhound bus traveling west on Route 50, thinking it was one of the many tour buses scheduled for the event. The bus stopped for the woman waving her arms, and she boarded and began giving her spiel to the bus full of confused travelers and an equally perplexed bus driver. No doubt all were enchanted by the chance encounter.

Ann’s driving over time became legendary, as evidenced by the dents and scratches on her own car. One day while driving through Middleburg on her way to tutor at Middleburg Elementary School — she was a devoted volunteer tutor at Windy Hill, as well — she was pulled over by town police for an unknown infraction. The coy, cunning, and always charming Ann diverted his attention, explaining that she was going to the school to tutor a young boy. “Sir, this little boy would love to meet a real police officer; would you be able to come with me to the school and meet him and talk to the children?” He complied with Ann’s will and a possible ticket was averted, supplanted by a wonderful experience for the officer and children.

Having lived through the Great Depression, Ann was conscientiously not wasteful. “She would say, ‘Oh, that’s perfectly good,’” recalls her son Colin. Whether it be moldy cheese or a broken item, not much in Ann’s life did she render useless. He recounts a time an old friend and house guest decided to clean out Ann’s refrigerator. “Oh, that’s perfectly good,” she repeated over his shoulder.

What was most evident and infectious was Ann’s relentless positivity. “Think lofty thoughts,” she would tell Colin. Or, “if you don’t have something nice to say, don’t say anything at all.”

For Ann, being upbeat was something she wore inside and out — always coiffed and dressed in classic clothes, known for her vintage wardrobe of dresses and hats.

Her positivity played out in all facets of her life. Her faith in God and his children was evident in her community involvement and daily life. She was curious about people and issues and had a yearning to understand all that she encountered.

Ann’s sense and sensibilities are further illuminated in this verse of a hymn she asked to have read at the close of her service:

Love can exclude no race or creed
If honored by God’s name
Our common life embraces all
Whose Father is the same

For all who knew Ann and all whose lives Ann enriched, 101 years seems not quite enough.

Featured photo by Kerry Phelps Dale.

Published in the May 2024 issue of Middleburg Life.