A Day and a Lifetime at The Saratoga Races

A Day and a Lifetime at The Saratoga Races

By Leonard Shapiro

It was August, 2018, and as always, Ann MacLeod was right where she belonged—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 an iron-woman streak, only because she had to miss one year to give birth to her son, Colin Bruce.

The stillness of dawn at Saratoga.

Photo © by Valerie Embrey

At the races one afternoon: Leonard Shapiro and Ann MacLeod.

Photo © by Vicky Moon

MacLeod has been a Saratoga fixture since 1958. She goes there to watch the races, to regularly 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.

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’s 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 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 threeday cruise that included chugging out briefly to the ocean, making their way to the Hudson River and then heading upstate to Schuylerville. They docked the boat there for Saratoga’s summer race meet, a 10- mile drive from the track.

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 a flamboyance of plastic pink flamingos she stuck in the ground out front.

Every day, after some morning tennis, she’s up in her box, usually surrounded by nearby patrons she’s known for years.

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.

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 has many Saratoga summers to recall.

This article was written in celebration of Ann MacLeod’s 96th birthday and has since been adapted for her 100th this past June.