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Features | Feb. 2025

THE RIDES OF HER LIFE

By Bill McLean

PHOTOGRAPHY BY MARIA PONCE BERRE
HAIR AND MAKEUP BY DORIA BARTOLO
STYLING BY THERESA DEMARIA

Equestrian Juanita Kennedy wearing Carolina Herrera top from Neiman Marcus, and her own vintage turquoise jewelry.

52 Equestrian Juanita Kennedy Wearing Carolina Herrera Top From Neiman Marcus, And Her Own Vintage Turquoise Jewelry

More than six decades ago, Juanita Wood Kennedy’s cousin babysat for a woman who lived near the ocean in Massachusetts. It led to Kennedy’s lifelong passion for sitting—in the saddle.

52 Bc2025 02 044 Juanita 21
Kennedy and her steed, Big Jerome.

“The woman was eccentric and owned two Arabian horses, one named Flame and the other Sieme,” recalls Kennedy, now 76 and a Barrington Hills resident since 1987. “I was 11 years old but she let us ride them. I rode Sieme on the beach, near cranberry bogs, and through the woods.”

The grandmother of four owns and takes care of two horses on her spacious property off County Line Road: an 18-year-old pony named Coco and a 21-year-old former off-track Thoroughbred named Big Jerome, who raced for eight years in his heyday.

Kennedy bought Big Jerome eight years ago.

52 Bc2025 02 041 Juanita 02
Juanita Kennedy wearing Eskandar black wrap, neimanmarcus.com and vintage pants, boots, and belt, model’s own.

“Thoroughbreds are spicier,” she says, smiling. Big Jerome and his owner join other horses and horseback-loving women for daily (weather permitting during nonwinter months) trail rides along Cook County Forest Preserves. Kennedy, the organizer, texts her fellow riders each morning to meet up for a trail ride at the Barrington Hills Park District Riding Center on Bateman Road.

“I feed Coco hay at 5 a.m. every morning and again at 7 a.m.,” Kennedy says. “Big Jerome gets hay and grain at those times. I then put Big Jerome in the horse trailer, and meet my friends at the riding center, where we tack up our horses. We usually start riding at 9:30 a.m., or 10, and go until noon or so.”

To Kennedy, the routine never gets old. It’s exercise, exposure to the great and beautiful outdoors, and an opportunity to engage in animated conversations with like-minded people, who range in age from 30 to 76, some actively working, others retired.

52 Bc2025 02 042 Juanita 23
Spurs adorn the back of a stable door.

“Sometimes three riders show up, sometimes there are 12 of us,” says Kennedy, “Some days are more fun than others. The type of day we have often depends on the horses’ moods and the weather— windy days can get exciting.”

“But I’ll always love riding, no matter the kind of day I’m having. Riding horses is like having a virus that you can’t shake. I can’t imagine a day without riding.”

She estimates she has owned 20 horses over the years. At 22, Kennedy rode her first off-track Thoroughbred, Flaming Fox, in Massachusetts. Her all-time favorite horse was named Stay Ahead, another off-the-track Thoroughbred.

“It’s not clean,” the delightfully straight-shooting Kennedy admits about her pastime. “But I get a lot out of it. It’s about getting horses ready, taking care of them, feeding them.”

It’s also occasionally about surviving harrowing flights.

“I’ve been bucked off and spooked off,” Kennedy says. “Anybody who rides horses knows what that feels like.”

52 Juanita 24
Juanita Kennedy’s functional and stylish stable.

Kennedy grew up in Plymouth, Massachusetts, and sprinted for her high school track team, sprinting in the 50- and 100-yard dash and anchoring the short relay when she didn’t have to report to a variety of jobs, including one at an egg farm and another at Gellars, a roadside shop that sold hamburgers, ice cream, and fried clams.

“Now, I couldn’t run from here to the corner,” laughs Kennedy, who used to lift weights “vigorously” and knows that a rider without core strength and coordination is a vulnerable one.

An honors student in high school, she enrolled at Northeastern University in Boston, majoring in education, and later earned an associate degree in nursing at Cape Cod Community College.

Kennedy and her husband, Taylor, an Elgin Academy graduate, are parents to Taylor, now 41, and daughter Katie, 40. After a trail ride, she usually joins her husband for an hour-long walk.

52 Bc2025 02 043 Juanita 11
Kennedy at home in her stable.

At 40, Kennedy learned hunter jumping from renowned instructors Diane Carney and Connie Curtis Stevens at Foxberry Farm, then located in Barrington Hills, and competed in local hunter jumper shows. A hunter course features up to 12 straightforward jumps. The jumps in an arena setting are meant to test the horse’s jumping form and manners.

A lifetime of riding has taught Kennedy that time atop a horse is recreational, therapeutic, and healthy.

“As Winston Churchill said, ‘There is something about the outside of a horse that is good for the inside of a man,’” Kennedy says. “That’s so true.”

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