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SIDELINESMAGAZINE | July/August 2026
here 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.
“I always said I would work with horses,”
Sydney said. “I just never imagined it would
look like this.”
WEST COAST TO WESTERN
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.’”
SYDNEY
RIVERA
TIDES, TRAILS AND CHINCOTEAGUE TAILS
By Tori Kistler
Sydney Rivera and Bertha, a mare who reminded
Sydney of her beloved first horse, Belle.