Saltwater Cowboys keep a century-long pony penning tradition alive
Words by Trudy Haywood Saunders
Once in a while, or maybe just once in a lifetime, you come across a place so unique, so fantastical, so divergent from the ho-hum world of social media and suburban shopping malls, that you have to ask, is this place real? Chincoteague,Virginia, is such a place.
In July 2025, the tiny town of Chincoteague will celebrate the 100th anniversary of Pony Penning Days, the annual event that draws tens of thousands to Chincoteague and Assateague Islands each year. The inspiration for the children’s novel, Misty of the Chincoteague, the horse-lover’s classic by Marguerite Henry, the history of how the ponies came to Chincoteague in the first place is shrouded in mystery. Tales of Spanish galleons wrecked off shore and even tax evasion are part of local lore. Throughout the 1800s, livestock men claimed ownership of the ponies and managed them, rounding them up and selling some to control the population. In an equally enigmatic twist, the Chincoteague Volunteer Fire Company became involved and began managing the ponies as an attraction for their fundraiser carnival.
“The whole thing is just amazing,” Hunter Leonard, Chincoteague Volunteer Fire Company’s Public Relations Officer, says. “A group of men decided that they were going to do a thing and it ended up turning into the lifeblood of the fire department and a lot of people around the world have heard of it.”
The annual event is held the last Wednesday and Thursday of July, with festivities kicking off the Saturday before the Pony Swim with the Southern Herd Roundup, and concluding the Friday after the Pony Swim when the Ponies swim back to Assateague. On Wednesday, the Saltwater Cowboys swim the ponies from Assateague Island to Chincoteague Island to be auctioned. The first foal ashore will be named King or Queen Neptune and will be given away in a raffle at the carnival. The Chincoteague Fireman’s Carnival with rides, games, raffles, and food is open nightly (Mon – Sat) with the film, Misty of Chincoteague, showing at the Island Theatre. “The government allows us to keep 150 ponies on Assateague,” Leonard says. “It was like a one in a million chance thing and the odds that we’re still doing it is still even slimmer.”
Saltwater Cowboys
The ponies are the stars of the show, but the Saltwater Cowboys are the supporting cast who make sure everything goes off without a hitch. A motley crew of firefighters, watermen, paramedics, contractors, a few ladies, and even a pastor, the cowboys—formerly called gumboots because the older generations would wear rubber boots—volunteer their time for the greater good of the community. “I’m one and there’s 45 others,” Leonard says. “You name about any profession on this island, you’ve got a cowboy out of it.”
Most of the time, the cowboys are multi-generational. “I think you’re kind of born into it,” Leonard says. He started helping when he was 14. His wife’s grandfather started helping when he was 10 or 11 years old and just stopped in his 70s and her dad picked it up from him.
“The best feeling I get is right there when we go and we’re putting them in the water,” Leonard says. “We’ve done two days to round them up. We’ve done a beach walk and got them all to the same place, had the big vet check, and we got them all the way out there to the swim site, about a two mile walk through the marsh.”
The saltwater cowboys come from all walks of life, but all have to be very adapted to riding. Once the ponies get in the water, it’s off of the fire department’s hands. “Even from a boy, when I was a cowboy right there cracking the whips and yelling and the ponies were getting in the water, I always thought that was the coolest part of it all,” Leonard says. “What starts as a pony round up turns into a swim across the channel where there’s 30-40,000 people cheering and watching. “There’s something about it. It’s just like the feel-good scene in a movie.”
Once in a while, or maybe just once in a lifetime, you come across a place so unique, so fantastical, so divergent from the ho-hum world of social media and suburban shopping malls, that you have to ask, is this place real?
The crowd, many of whom read Misty as children, are right next to the cowboys as they parade down the street, happy and thankful to experience a scene from their childhood dreams.
“We’re not important people, so to speak,” Leonard says. “We’re not sports stars or politicians or anything like that. We don’t see people act like that all the time, so it’s very fulfilling. A lot of the guys take great pride in being able to give that to people along with doing their job for the fire department.”
A Horse of a Different Color
Hold onto your derby hats. These other Southern locales have something for equestrian lovers of all kinds.
Pinehurst, NC- Pinehurst Harness Track- A lot of the harness track race horses from up north winter in Pinehurst, and they have a big matinee race at the end of the winter season before they return home in early April. Pinehurst’s version of the Kentucky Derby, many visitors dress up with hats to attend the event.
Ocala, FL- The World Equestrian Center- The largest equestrian complex in the United States, The Equestrian Hotel has rooms that look directly down on the arena. The property hosts equestrian events year round, and well as dog shows, and the Winter Wonderland Christmas event.
Charlottesville, VA- Fox Hunts
In the middle of Virginia horse country, Farmington Hunt Club has featured hunting with hounds since 1929. If you’re looking to experience traditional English fox hunting with red jacket attire and Blue Ridge Mountain views, this is the place.
