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Jul 29
Chincoteague mare grazing on the marsh by the Eastern Shore of Virginia Tourism Commission

The Saltwater Cowboys of Chincoteague Island

a saltwater cowboy working at the 2019 Pony Swim

The Pony Swim in 2019

The American cowboy is the stuff of legends. Stories of guys on horseback working in the sun all day to build the American west have fascinated, intrigued, and maybe even confused us for years. Cowboys have become a symbol of American ingenuity and diligence. But did you know that Virginia’s Eastern Shore has its own cowboys?

Chincoteague Saltwater Cowboy swims the wild ponies across from Assateague to Chincoteague in the 2019 Pony Round Up

2019 pony round up saltwater cowboys

Pony Penning 2019

Captain Hunter of Cowboy Cruise Company. Photo credit to Cowboy Cruise Company

We had the opportunity to join Captain Hunter of Cowboy Cruise Company for a tour around the marshes of Assateague Island to learn all about the Chincoteague ponies and the Saltwater Cowboys.

Riptide, the King of the Southern Herd, makes the swim in the 2019 Pony Round UpRiptide, a stallion from the Southern Herd, makes the swim in 2019

Riptide, the King of the Southern Herd, makes the swim in the 2019 Pony Round Up

Did you know? Captain Hunter refers to Riptide as the King of the Southern Herd. He has a distinct, rare color with his dark coat and blond mane and tail. He has a firmly established group of mares and even if one wanders off, they always return back to his group.

A mare from Riptide's group off grazing with her foalA mare and foal from Riptide's herd graze separately from the others

A mare from Riptide’s group off grazing with her foal

This mare was off separately from the rest of the group, but even as we watched the ponies, we saw her moving back towards the rest of the ponies.

The Saltwater Cowboys of Chincoteague are the picture of people that love their community. They are firemen on the Island and they spend time that they are not volunteering at the fire station working in the community or taking care of the ponies.

Saltwater Cowboys swimming the channel with the Chincoteague Ponies in the 2019 Pony Round UpThe ponies swimming across the channel in the 2019 Pony Round-Up

The Pony Swim 2019

Caring for the ponies may be a little more complicated than it seems. While it may look like the ponies simply roam the Island, but each pony has a name, is branded with their birth year, and is observed to see if they need vet care.

Chincoteague pony grazing on the marsh. Picture was captured on the Cowboy Cruise tourChincoteague ponies on the marsh

Chincoteague ponies on the marsh

They can keep only a certain number of ponies on the Island in order to keep the population healthy and thriving! Foals are sold every year at the annual pony auction. Normally, the auction is held as part of a three-day tradition that involves the world-famous pony swim, a parade, and the carnival. Due to recent limitations on events, the 2020 auction was held online and this year it will also be online. With things starting to return to normal, we are hoping that the pony swim and all the fun activities will be held in person again, but the online auction will also be here to stay!

Chincoteague mare grazing on the marsh. She is one of the descendants of Misty that lives on the Island.A mare descended from Misty

Chincoteague Mare descended from Misty

Did you know? The bloodline of Misty actually left the island of Chincoteague for a period of time. After many years, ponies descended from Misty were able to be located and the bloodline was reintroduced to the wild ponies on Chincoteague Island!

The Southern Herd of Chincoteague Ponies grazes in the marshThe Southern Herd

The Southern Herd

While you can of course purchase some of the ponies on your own, a certain number are selected as buybacks, which means they are named and then donated back to the Fire Department.

A brown and white foal checks out our boat on the Cowboy Cruise tourA young foal from the southern herd

This foal came right up to the boat!

This little foal was sick when he was very young, so he lived at the carnival grounds while he was nursed back to health. He was very curious and even tried to eat our bowline! While some of the ponies are very friendly, remember that visitors are not allowed to touch them.

There are also two herds on Chincoteague that the Saltwater Cowboys manage. The horses are split into the Northern and Southern herds to help prevent the ponies from becoming too closely related and to also allow for the Cowboys to keep track of ponies for vet care more easily.

Two foals from the Southern HerdPinto foal on the Assateague Island Marsh

A foal from the Southern Herd

If you’re looking for a way to see the ponies up close, the Chincoteague pony tours are a great way to do it. Cowboy Cruises is one of these companies. Owned and operated by Hunter, one of the Saltwater Cowboys, it’s an immersive experience where you will not only learn about the ponies, but about the history of the Island and the Saltwater Cowboys, the culture, and the best things to see and do while you are visiting. Coast around the channels and enjoy the sun, salt, and ponies in a unique way!

A dark brown foal and mare from the Southern Herd grazingA mare and foal from the southern herd

Foal and mare in the Southern Herd

The Southern Cowboys look a little different from the cowboys we may be used to seeing in movies or reading about in books, but their dedication to their community and their work makes a difference on Chincoteague and shows in how happy and healthy the ponies are.

About Cowboy Cruise Company and Captain Hunter

Captain Hunter at the Pony Swim

Pony Swim with Captain Hunter of Cowboy Cruise Company

Photo by Cowboy Cruise Company

Captain Hunter is a Chincoteague local, born and raised, and has spent his whole life interacting with and observing the famous Chincoteague Ponies. He is an expert in individual pony names, herd territories, bloodlines of the ponies, and even can identify which year each one was born. He is a fourth generation Saltwater Cowboy. His family has been a part of the fire company and the management of the ponies since it all began in 1925. His grandfather, Donald Leonard, was an iconic and influential manager of the ponies and he worked hard to improve the care of the herd, developing effective practices which have been passed down to today’s managers.

Captain Hunter grew up going out on boats and got his very first 13 foot boat with a 25 HP motor at 12 as a gift from his grandfather. Eventually, he obtained his captain’s license and worked with his Uncle Carlton at Daisey’s Island Cruises, another well-known pony tour company on Chincoteague, for 6 years.

Being a saltwater cowboy is a family tradition for Captain HunterHunter working at the 2019 Pony Round-up

Photo by Cowboy Cruise Company

Now, in addition to serving the community through the Chincoteague Fire Department and managing the Chincoteague Ponies as a Saltwater Cowboy, Captain Hunter gives visitors the tour of a lifetime through Cowboy Cruise Company, expertly taking them around the marshes of Assateague and Chincoteague to see ponies, birds, and other wildlife that calls the pristine area home. Learn each pony’s name, origin, and personality on the tour and get an up-close and personal look at how they live.


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