Meet the toughest, oldest of the Saltwater Cowboys

At 86, Jack Brittingham of Powellville is the oldest riding Saltwater Cowboy taking part in the annual Chincoteague Fire Company’s annual pony penning event.

Just like an old aged Virginia country ham, cured with plenty of salt to last, cowboy Jack Brittingham is riding tall in the saddle with staying power too.

He is a genuine Saltwater Cowboy of Chincoteague fame, a bonafide horse lover through and through who has been helping fellow cowboys round up wild ponies for 40 years.

That’s 40 continuous, uninterrupted, never called-out-sick once years. At 86, the cowboy crowd knows they can still rely on Brittingham to be in the saddle to round up Assateague Island’s legendary ponies for the annual pony penning and auction every July on Chincoteague Island. He is the oldest Saltwater Cowboy.

His life has always been about horses, sulky racing, dancing.

He’s the real country cowboy deal.

He’s still proud of being the winner of the “Tight Fittin’ Jeans Contest.” This wasn’t just a fun contest among seniors with a beer as a prize. Top prize was a free trip to Nashville. “Won that when I was 60,” he said with pride.

“I use to do a lot of line dancin’,” he said. He is so light on his feet that he soon became the Fred Astaire of the boot scootin’ crowd and his dance card was booked.

He lives on the farm near Powellville where he was born and raised, and its where he keeps his two ponies, Red and Harley. There must be something special in the water in these parts as more than a dozen locals, over the years, have also been Saltwater Cowboy.

“I had a younger brother, Chester,. now deceased, who rode with the cowboys  before I did. A lot of the boys from Powellville rode to Chinctoteague for the pony penning and still do. We knew a lot of people down there 40 years ago and got invited to ride,” he said.

Decades ago, the cowboy explained, the island’s fire company company which sponsors the penning and sales even, didn’t have enough riders. So folks off the island were invited to help out.

“It was hard riding back then, hard,” said Brittingham’s friend, Dan Massey of Deal Island, “and these Powellville guys were used to riding hard so they went on down to help with the round up.”

“As the years passed the younger “Chincoteaguers” wanted to ride,” Massey said, “and the older guys still have a foothold because they ‘started back when.’ ”

Like the other men from the area, Brittingham grew up on a farm and worked with teams of horses and mules.

“When I was 14, I plowed with a walkin’ plow with horses or mules, dragged the land with a drag, planted corn with horse teams,” he said. “I was so young I couldn’t even look over the handles of the plow.”

His grandfather set aside 20 acres that Brittingham worked as a share cropper with his grandfather.

It was growing up with horses that set the stage for Brittinghgam becoming a skilled cowboy from the old school. Not many people today can say they helped move to their new home with horses.

 “When I was about six we moved from my grandparents house to the farm where I live now. We used horses and a cart to move all our stuff.”

 Beds, tables, chairs, even the old wood stove, was moved in a horse cart across the fields. “We were going modern over here, we had an indoor hand pump,” he said, laughing.

Brittingham had a chance to relive elements of that youthful experience was he got a job as a carriage driver during the filming of the movie Tuck Everlasting, in 2002, in Berlin.

“I answered an ad in the paper for the job, I had a carriage and the horses. In period costume, Brittingham was convincing as a rural character of the late 1800s. “Pretty good pay,” he said. 

As a cowboy, he has been captured on video by national and international news media. High in the saddle, 86-year-old Brittingham is “just one of the boys.”

It’s pure ecstasy with hooves churning mud, kicking up sand and water, the flies and humid heat, the smell of leather and wet horses, and the crack of his whip encouraging ponies to move along.

Jack Brittingham starts to saddle up Red, his other pony, Harley, watches. Brittingham rides Red, an island pony, during the annual pony penning event on Chincoteague Island.

“The mosquitoes are so bad we just rake them off us,” he said.

 Of course when he and his brother “joined up” with the seasoned cowboys, neither knew anything about rounding up wild ponies.

“We just ‘git in,’ and follow the Chincoteaguers orders,” he said, “they know all about it.” Soon as you start ridin’ you are a Saltwater Cowboy.

It was then that the experience he got on two genuine cattle drives, that Brittingham had participated in Wyoming and Colorado, years ago, paid off.

Three times a year his horses are loaded onto a trailer and hauled to Chincoteague where Brittingham stays for a week.

Cowboys are not paid, and the out-of-pocket expenses for the traveling cowboys adds up fast. Brittighman said he figures it costs him about a $1,000 a visit.

Money well spent, he says, because it helps the community and the fire department. Plus, every year is a memorable ride.

The annual routine is predictable. 

“On Saturday morning we work the south end of Assateague Island and put the ponies in a coral. Sunday morning we go up to the north end, at the Maryland line, and put them in a holding coral. On Monday we take the north end ponies out to the surf for take them down for about five miles to the south end. 

“On Tuesday you have all of them herded into one coral. On Wednesday, we take them out, move them over the marsh and swim about 130 of them across the channel. Come Thursday, we separate the colts, sell them, then on Friday swim the herd back across the channel,” he said.

He’s been following this routine for 40 years.

With years of service, cowboys becoming honorary members of the Chincoteague fire company.

He’s had four different horses since he started, and Brittingham keeps on riding. The attraction is the camaraderie of cowboy experience. “It’s like a reunion, there are guys riding that come from all up and down the seaboard,” he said.

Because the ponies are rounded up three times a year, there’s plenty of socializing.

‘A lot of people don’t know that. We round them up in the spring and fall to check on their medical condition. But the only time we ‘swim them,’ is in July, during the carnival pony penning,” he said.

Year after year, the 86-year-old cowboy helps make the pony event a success.

“It’s true, he’s the oldest riding cowboy we have,” said Denis Bowden, spokeswoman for the Chincoteague Fire Company Pony Penning group.

“We could never have the pony penning if it wasn’t for Jack and the other 45-50 volunteers,” she said.

After two devastating fires on the island prior to 1924, members of the community organized the fire company. 

Jack Brittingham joins other Saltwater Cowboys as he helps move wild ponies on Assateague.

“They passed the hat and raised a big $4.16. That’s how we got started. I don’t know what they first few pony auctions raised, but I doubt if it was more than $1,000. Our pony auction this past July raised $271,000,” she said, with the average price per pony around $4,300.

“In the 1960s, ponies were going for $25 to $50 each. It’s only been in the last 15 years that we have seen prices soar. 

 “My family and Jack’s family have been friends for years. Each year, I Jack is the first person I’m looking for as they are coming through the woods. It makes my heart light up when I see him, because, at his age, there he is riding that horse and I know there’s no other place in this world he’d rather be than doin’ what he’s doin.’ He’s a real Saltwater Cowboy.”

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