Photos by Kayla Colonna
There are some stories stitched into the fabric of almost every horse girl’s dreams. Long before social media, there were well-loved, dog-eared copies of a book about an island pony tucked into backpacks or resting on nightstands. For many young riders, the dream ended on the final page. For Sydney Rivera, it became her real life.
Today, Sydney captains pony tours through the marshes of Chincoteague Island, owns several of the island’s famous ponies and continues to chase her dream of upper-level eventing. But her path from Southern California horse shows to the salt marshes of the East Coast was anything but straightforward.
Born and raised in San Diego, California, Sydney grew up in a horse family. Her mother rode Welsh ponies and Saddlebreds, so horses were part of life from the very beginning. Still, it was the mare Sydney got when she was 15 that truly changed everything.
“She wasn’t even for sale,” Sydney said. “But I fell completely in love with her and insisted she was the one.”
Every weekend, she rode Belle to the beach. Together, they climbed through the jumper divisions, eventually earning the coveted Centaur Award at their local show grounds—an all-around championship recognizing consistency and horsemanship throughout the season.
“We were having this incredible show year,” Sydney recalled. “She’d moved up into the three-foot jumpers and honestly surpassed what anybody thought she could do.”
One morning, Belle slipped in her stall and became trapped beneath the door. Though Belle’s leg wasn’t broken, the injuries were significant. After emergency surgery and weeks at the veterinary hospital, complications spiraled. “She spent 46 days there,” Sydney said. “She was my everything. It was like every possible thing that could go wrong did.”
The loss nearly ended her riding career. “I was done,” she admitted. “I didn’t want anything to do with horses anymore.”
But true horsemen and -women often find it hard to walk away from this life altogether. Friends pushed her gently back toward the barn, and eventually she met a trainer, Taya, who helped reshape her relationship with riding entirely. “She told me, ‘You’re not going to stop riding. We’re just going to change your perspective on things.’”
Instead of chasing jumper rounds, Sydney found herself learning the art of barrel racing aboard a chestnut Quarter Horse. Somewhere between the speed patterns and dusty arenas, she fell in love with riding again—enough to win a barrel racing buckle along the way.
Soon, new horses found their way into her life. There was Bambi, the Thoroughbred her trainer Taya acquired for free and eventually sold to Sydney after the pair bonded instantly. There was the Quarter Horse who unexpectedly became a successful three-foot jumper after Bambi suffered an injury.
And there was Bertha, the horse Sydney swears was sent to her for a reason. “The horse looked exactly like my first mare, Belle,” Sydney said. “And when I asked her to canter, it was the exact same terrible canter.”
Without telling her, Sydney’s father secretly bought the mare, Bertha. At a horse show, he walked her out into the arena wearing a giant bow around her neck.
The horses kept coming after that—a baby horse who turned out to be a half-brother to her first mare, then another half-sibling discovered years later, and even a cloned Dutch Warmblood descended from the Grand Prix horse Pacifico. Each horse carried its own story, but none would ultimately change Sydney’s life quite like the spunky ponies she first encountered thousands of miles from home.
Like countless horse girls before her, Sydney grew up reading “Misty of Chincoteague.” “Every horse girl growing up reads it,” she said. “It’s just a rite of passage.”
In 2017, she traveled to Chincoteague Island for Pony Penning, the annual celebration made famous by the novel. The trip became life-changing almost immediately.
At the time, Sydney was terrified of boats, so she watched most of the festivities from shore. But one of the local captains’ daughters took her on a beach ride to see the island ponies. She also visited the farm where the fire company cares for any injured horses and there Sydney spotted a small colt without a brand, grazing in a pasture.
That colt—eventually named Curly Fry Extra Salty—was the beginning of an entirely new chapter for Sydney and her family. They returned to the island again and again. During one Christmas parade, she realized something had shifted. “I remember thinking, I really belong here.”
In May of 2018, Sydney moved to the island alone while helping her family search for a permanent East Coast home. She started working for a local boat tour company—despite still being deeply afraid of the water. “They convinced me to go out on the boat for Pony Swim that year,” she said. “I was terrified but watching it from the water was incredible!”
Slowly, the island changed her. Local friends coaxed her out onto docks and into marshes until eventually she realized the famously shallow waters were often barely knee-deep. “One day they told me to jump off the dock,” she laughed. “I sank straight into the mud because it was only about a foot and a half deep.”
The girl once terrified of boats eventually earned her captain’s license—the hardest thing she has ever done. Today, Sydney leads tours through the same waterways she once feared, sharing stories about the island ponies with visitors who grew up loving them as much as she did.
Last year marked her first time captaining her own boat during Pony Swim, a full-circle moment she wishes she could have shared with her late friend and mentor Carlton, whose passing helped inspire her to pursue her license in the first place. “The little island ponies of Chincoteague changed the whole trajectory of my life,” she said.
Horses remain at the center of everything Sydney does. She still events and recently started a promising young Thoroughbred, Andarna, expected to become her next upper-level prospect. Her goal is to one day event her at the Kentucky Horse Park.
“This is where knowing people in the horse world really matters,” Sydney said. The mare, originally intended for racing, proved too large to succeed on the track. Concerned about finding the right home, the owner ultimately gifted her to Sydney instead.
At home, Sydney’s herd now totals 10 horses and ponies, including five retirees. Sydney’s daughter Chloe has already started catching the horse bug herself. “She asks every weekend if we’re going to another ‘unicorn show,’” Sydney laughed.
In March, Chloe completed her very first leadline starter trial aboard her dad’s horse, Aurora—a homebred. She plans to continue horse showing right alongside her mom and is eagerly awaiting the day she can show her very own Chincoteague pony, Cheese!
Sydney believes Chincoteague ponies are unlike anything else in the horse world. “They’re smart. They’re brave. They’ll ride through anything,” she said. “You want an all-around horse? That’s what they are.”
On the island, the ponies survive harsh weather, sparse grazing and difficult terrain. Under saddle, that toughness translates into remarkable versatility. In Sydney’s area alone, multiple Chincoteague Pony owners now compete successfully in eventing and dressage. “They have the biggest personalities,” she said. “And they’re such easy keepers because they’re used to such a bland diet.”
Sydney occasionally rides with the local pony drill team and even traveled to BreyerFest last year to help share the story of the island ponies with a wider audience. She has also had the surreal opportunity to ride Misty III—part of the continuing legacy where each generation selects a new mare to carry the iconic name.
“It’s just kind of wild,” Sydney said. “This little pony I used to read about changed my life so much.” The island is also where Sydney met her husband, Ramsey. He jumped right into this incredible journey with Sydney, supporting her and encouraging her to chase after all her dreams.
For all the adventures, awards and unexpected turns, Sydney says the greatest lesson horses ever taught her came from heartbreak. “With everything that happened with my first horse, not knowing my last ride was my last ride—my best advice is don’t leave the barn upset,” she said. “Always thank your horse. Be patient. Find at least one good thing from your ride,”—a lesson she hopes to pass on to her daughter as she learns to love horses.
For all the horse girls out there dreaming of an island pony adventure, Sydney encourages everyone to experience it at least once in their lifetime—and you never know, it might just change the trajectory of your life as well.
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