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SARATOGA WAS SO VERY SPECIAL TO ANN MACLEOD
SARATOGA WAS SO VERY SPECIAL TO ANN MACLEOD
By Leonard Shapiro
Long-time Upperville resident Ann MacLeod passed away at her home on April 10, 2024 at the age of 101. In her memory, the following is a story that ran in Country ZEST five years ago.
As always, Ann MacLeod was right where she belonged a few weeks ago— sitting in her clubhouse box overlooking the finish line on opening day at the Saratoga Race Course. Old habits are hard to break, don’t you know.
“The Widow,” as she’s affectionately known to her legion of friends back home in Upperville, was celebrating 60 years since she first started coming to “The Spa” and its iconic thoroughbred racetrack. It’s quite a Ripken-esque iron-woman streak, only because she had to miss one year to give birth to her son, Colin Bruce.
Now 96, MacLeod has been a Saratoga fixture since 1958. She goes there to watch the races, to attend concerts, plays and the ballet at the Saratoga Performing Arts Center and to play lawn tennis on the grass courts at the Saratoga Golf and Polo Club. (We donated a chair in her honor at the Saratoga Performing Arts Center.)
She did all of the above, including the tennis, during her three-week stay. Back in Virginia, she has a regular doubles game at The Middleburg Tennis Club at least three times a week, and sometimes four if an emergency replacement is needed at the last minute. She only lives a few miles away, and yes, of course, she drives herself, so hold the Miss Daisy.
A few years ago, before a morning tennis match in Saratoga against then jockey Jerry Bailey and his wife, MacLeod had a bit of strategic advice for her own partner before they took the court.
“Always lob the jockey,” she told me.
MacLeod was a native of Staunton, Virginia. Her love affair with Saratoga began with her love affair with her late husband, Colin “Sandy” MacLeod, who passed away in 1977. They owned a 150-acre farm in Upperville and bred racehorses. Sandy MacLeod also was a successful trainer, and for a good part of every year, they had barn space at Belmont, Aqueduct and Saratoga.
Their own space back then was the 60-foot boat they lived on—The Dunvegan, built in 1924 and also the name of their Virginia farm. It was anchored at Lookout Point on Long Island, conveniently located for short, 20-minute commutes to the nearby racetracks.
For Saratoga, the MacLeods embarked on a three-day cruise that included chugging out briefly to the ocean, making their way to the Hudson River and then headingupstate to Schuylerville. They docked the boat there for Saratoga’s summer race meet, only a 10-mile drive from the track.
“It was a wonderful time,” MacLeod said the other day, “and we always loved Saratoga. Sandy’s family had a box there going back to 1932. There’s so much to do in Saratoga, and over the years I’ve made so many friends. I know so many Saratogians, and it’s just a fabulous place to be.”
After her husband’s death, the Dunvegan was sold and MacLeod spent her upstate nights on dry land at several locations around town. For many years, she shared a small house that was always easy to find. You only had to look for the gaggle of plastic pink flamingos she stuck in the ground out front, far easier to spot than the smallish numbers on the house.
The last few racing seasons, she’s been staying in a home owned by a couple she met in church. And every afternoon, after some morning tennis, she’s up in her box, usually surrounded by nearby patrons she’s known for years. If anyone has extra guests, they all know someone nearby will probably have a spare seat or two for the spillover.
One afternoon a few years ago, a fellow with a thick New York accent dressed in a designer suit dropped by and sat down in MacLeod’s box. Soon, they were engaged in a spirited conversation. At the time, MacLeod had no idea who she was talking to until a friend later told her she’d been yakking with Al Pacino.
MacLeod has made countless friends in the horse world, and one of her best pals is Lenny Hale, former executive director for NYRA who now lives in Baltimore. He drove her up to Saratoga this year, and another Virginia neighbor will take her back.
She’ll surely regale him with countless stories, maybe from her days as a CIA operative in Salzburg, Austria in the early 1950s, or her work as a Red Cross volunteer in Europe during World War II, or how she helped save a historic Civil War bridge back home from greedy developers, or perhaps about her organizing her church group to feed the homeless in Washington, D.C. She still rides the church van into town with them, as well, and works the serving line.
For sure it’s been a rich, rewarding and fascinating life for Ann MacLeod, who also shows no signs of slowing down save for a little loss of hearing. She’ll surely be packing her Saratoga trunk in 2019 for her official 60th opening day. And she’ll surely find a little court time to lob another jockey, as well.
