450-Mile Solo Horse Drive In 1984 Was One Of Wyoming's Last Over Outlaw Trail

Larry Bentley was hired to trail 30 quarter horses for 450 miles alone across Wyoming and into Colorado. It was 1984, and Bentley took these horses over the Outlaw Trail, where the Hole in the Wall gang used to trail their stolen horses 80 years before.

JD
Jackie Dorothy

November 15, 20259 min read

Larry Bentley, inset right, was hired by Ashley Kent Carrithers, left, to trail 30 quarter horses for 450 miles alone across Wyoming and into Colorado. It was 1984, and Bentley took these horses over the Outlaw Trail, where the Hole in the Wall gang used to trail their stolen horses 80 years before.
Larry Bentley, inset right, was hired by Ashley Kent Carrithers, left, to trail 30 quarter horses for 450 miles alone across Wyoming and into Colorado. It was 1984, and Bentley took these horses over the Outlaw Trail, where the Hole in the Wall gang used to trail their stolen horses 80 years before. (Val Duncan, Kenebec Images via Alamy; Courtesy Patagonia Land Havens)

Cowboy Larry Bentley had his work cut out for him.

He had just driven 30 horses plus six of his own into Thermopolis. These quarter horses, with a few Arab crosses, were fresh off the range and saw green grass. They scattered, and Bentley said women with brooms were soon in their yards, shooing the horses away.

“They were fresh and they weren’t used to traveling,” Bentley said. “This was all strange to them.”

Bentley had trailed the herd about 20 miles from Highland Ranch, a ranch along Cottonwood Creek, west of Hamilton Dome. Bentley and the herd had just come down the road west of Thermopolis when the horses decided to go their own way.

“We came off that hill, and they could look down and see all the green grass growing in the yards, I guess,” Bentley said. “We came off the hill pretty fast, and they scattered quick, went several ways, and there were a lot of ladies who didn’t think they needed horses in their front yard.”

It was the summer of 1984, and Bentley had been hired by Ashley Kent Carrithers to trail the horses over 450 miles to Carrithers’ ranch on the Colorado-Utah border.

Carrithers, newly divorced from heiress Catherine Conover Mellon, was selling out his Wyoming interests and planned to join Bentley on the last leg of the trip.

By the 1980s, ranchers were trucking their stock rather than expending effort and expense to trail horses across long distances.

Thus, this unique trip caught the imagination of the press and attention of locals as Bentley made his solo trip across the state.

Unintentionally, Bentley was also reenacting the horse drive of outlaw Tom O’Day, who in 1903 was caught trailing 20 stolen horses across the same country. 

Larry Bentley drove a herd of 30 loose horses and six of his own on a 450-mile solo trip across Wyoming and Colorado in 1984. Along the way, Bentley trained six horses, lost his packs, had his herd threatened by romantic wild horses, and was mistaken for an outlaw twice. It was a trip of a lifetime and earned him a place in the Cowboy Hall of Fame.
Larry Bentley drove a herd of 30 loose horses and six of his own on a 450-mile solo trip across Wyoming and Colorado in 1984. Along the way, Bentley trained six horses, lost his packs, had his herd threatened by romantic wild horses, and was mistaken for an outlaw twice. It was a trip of a lifetime and earned him a place in the Cowboy Hall of Fame.

The Horse Drive

After being hired to trail the horses to Carbondale, Colorado, Bentley decided to take six young pack horses of his own to train on the way. He was the lone cowboy on the trip, and he described his first stop at Thermopolis in one word.

Chaotic.

It took Bentley about three trips to round up all the horses that had scattered among the homes of Thermopolis, and he corralled them in the Hot Springs County Fairgrounds for the night.

“I wanted to see if I could tire them out,” Bentley said. “They were easier to handle the next day, except they bucked all my packs off. But that was my own horses.”

Bentley kept the horses bunched together and drove them out of Thermopolis the next day to the Heinz place on Buffalo Creek. His plan was to stop each afternoon after about 20 miles and make camp before the sun set. Each morning, he would trade out his saddle horse so that each one of his six quarter horses got in their training.

“I’d get up about 4:30 every morning and eat some breakfast, and then we’d hit the road,” Bentley said. “We’d travel till about ten in the morning, and then they’d want to stop and graze until about 2:30. By three in the afternoon, they’d bunch up again, and we would hit the road again for another couple of hours.”

The herd fell into a rhythm, though it wasn’t without its headaches. Not only was Bentley trying to train six young horses, but he had to keep the herd together. Fortunately, a gray Arab gelding took the role of lead horse, and the rest would generally follow him.

When they finally reached Lysite, Bentley was hungry and in desperate need of coffee.

On the Path of Outlaws

“I had so many wrecks with my pack horses that all I had left was my bedroll,” Bentley said. “I had a can of Dinty Moore stew and an onion.”

He placed the horses in the shipping corrals near the old railroad tracks and went into town. It was raining, and so he put on his slicker, riding into Lysite on one of his own horses. He caught the attention of an older man who came out into the rain.

“You going to rob the bank?” he asked Bentley.

Bentley answered no, and the man nodded.

“Well, the last rider that came into town like this was one of the Wild Bunch,” the old man said.

Bentley responded that he was just going down to the store for some coffee. However, the store was closed, so the older man left and came back with a baggie of ground coffee. He presented this to Bentley, who gratefully accepted the gift.

The coffee warmed Bentley so that the night was more tolerable. The next morning, Bentley replaced the supplies his horses had bucked off and headed to the highway.

“I was going from there to Sweetwater down to Jeffrey City,” Bentley said. “My plan was to camp along the way.”

Ashley Carrithers hired cowboy Larry Bentley in 1984 to move 30 horses across the state of Wyoming from High Island Ranch to his ranch in Colorado. It was one of the last horse drives across Wyoming and turned into an adventure of a lifetime for Bentley who was joined on the last leg of the journey by Carrithers.
Ashley Carrithers hired cowboy Larry Bentley in 1984 to move 30 horses across the state of Wyoming from High Island Ranch to his ranch in Colorado. It was one of the last horse drives across Wyoming and turned into an adventure of a lifetime for Bentley who was joined on the last leg of the journey by Carrithers. (Courtesy Patagonia Land Havens)

The Wild Romeos

However, it didn’t work out that way. Every time Bentley stopped and set up his rope corral, wild horses would try to sneak in to steal some of his mares.

“Mostly it was young stud horses that were trying to get a few mares put together as a band,” Bentley said. “They could smell that the mares were in there.”

These wild stallions had gotten curious enough about the mares to put aside their fear of Bentley when he stopped to make camp.

“I couldn’t take a chance on a stud taking my mares,” Bentley said. “If he took them in the dark, they could be 15 miles away before I knew they were gone.”

To protect his mares, Bentley had to ride throughout the night. He kept the horses bunched together, and the young hopefuls were unable to build up their wild mustang herd with Bentley’s horses. He reached the town by 8:30 the next morning.

“When we pulled into Jeffrey City, the uranium boom had just ended, and it was almost a ghost town,” Bentley said. “They had a baseball field, and the fence was around the outfield and behind home plate, so I put my rope corral across there and turned the horses in on the grass.”

After a long night of riding, Bentley went over to the restaurant and discovered that the special was chicken-fried steak.

“I hadn’t really eaten anything since I left Lysite the morning before, so I told the waitress that I wanted two of those specials,” Bentley said.

She asked him if he had company coming, and he replied no, that they were both for him.

With a full stomach and warmed by more coffee, Bentley camped out with his horses in the baseball field.

Accidentally Reenacting the Outlaws

The next morning, Bentley was getting ready to leave when he was stopped by the deputy sheriff.

Bentley had already turned the herd out on the open range and was just passing through the gate of the field himself when the sheriff demanded to know if he had gotten permission to stay in the baseball field with his horses.

Bentley replied that he hadn’t, and the deputy kept asking more heated questions.

“Finally, I told him that he was going to have to shoot me because I’m going with my horses,” Bentley said.

Bentley rode off, and the sheriff pulled his gun.

“I kept my back really stiff like that would stop the bullet,” Bentley said. “But he let me go.”

Bentley fell back into a routine of riding, eating, and sleeping. Each night, he would stake out his rope corral and bunch the horses together. In the morning, he would trade out the saddle horse and start the day.

“It takes a little while to get a horse broke to a rope corral,” Bentley said. “But they’re easier to catch. If you walk out in a five-acre pasture, you’re going to wear yourself to death chasing them down.”

Bentley said that once trained, horses were easier to trail than cattle because they were creatures of habit and herd animals.

“Once they got used to the road, they’d get up about on their own,” Bentley said. “I got to Baggs, and I had to go east a little bit to get across the border.”

Since riding 450 miles across Wyoming and Colorado with a herd of 30 loose horses and six pack horses of his own, Larry Bentley has settled down on his own spread in Hot Springs County with his wife, Chris.
Since riding 450 miles across Wyoming and Colorado with a herd of 30 loose horses and six pack horses of his own, Larry Bentley has settled down on his own spread in Hot Springs County with his wife, Chris. (Courtesy Chris Bentley)

Parade of Horses

Bentley trailed the horses into Colorado and stayed in the national forest all the way to Aspen. It was outside of Aspen that Carrithers joined the outfit.

“Ashley shows up with his girlfriend, his sister and her husband and some others,” Bentley said. “He wanted to parade through Aspen from one side to the other.”

They camped that night and came into Aspen, creating their own impromptu parade.

“We got in parading through Aspen, and I was showing off,” Bentley said. “I was roping the front feet on my horse as we went through the town just because I was bored more than anything.”

This caught the attention of the polo players, and before the parade was over, Bentley had sold all six horses that he had trained on his solo trip.

“The polo players liked the fact that they could stand the rope around their front feet,” Bentley said. “Quarter horses are muscular. They’re like a bulldog.”

It was another 30 miles to the ranch in Carbondale, so soon after the celebrations, Bentley was back in the saddle, though he admitted he was a little worse for the wear.

“It was not a good day because the mayor of Aspen and I had way too many drinks that night, and we were doing the bunny hop down Main Street together,” Bentley said.

Despite this, Bentley was able to successfully bring all 30 horses to their new home in Carbondale. It was a historic trip following the old outlaw trails and one that has never been done again, as far as Bentley is aware.

This trip, and a lifetime of cowboying, earned Bentley a place in the Wyoming Cowboy Hall of Fame. However, his biggest prizes are his family and the cattle operation he now owns and manages with his wife, Chris, in Hot Springs and Fremont counties. He is still in the saddle today, keeping the memories alive of his adventures in the Cowboy State.

Jackie Dorothy can be reached at jackie@cowboystatedaily.com.

Authors

JD

Jackie Dorothy

Writer

Jackie Dorothy is a reporter for Cowboy State Daily based in central Wyoming.