Pony Express Riding Through Wyoming In Annual Re-Ride This Weekend

The annual National Pony Express Association’s re-ride was kicking up dust through central Wyoming on Friday, and will be blazing a trail through the Cowboy State until early Sunday.

DK
Dale Killingbeck

June 21, 20246 min read

A rider between Glenrock and Casper covers her 2 miles of ground as part of the National Pony Express Association’s 2024 re-ride.
A rider between Glenrock and Casper covers her 2 miles of ground as part of the National Pony Express Association’s 2024 re-ride. (Dale Killingbeck, Cowboy State Daily)

The National Pony Express Association’s annual re-ride of the famous Pony Express route between St. Joseph, Missouri, and Sacramento, California is galloping through Wyoming and kicking up dust again in the Cowboy State.

Riders entered Wyoming from Nebraska on Thursday evening and are scheduled to leave the state south of Evanston about 2 a.m. Sunday.

The association’s Wyoming President Les Bennington, 77, plans to follow the riders the entire route in his truck and trailer of horses.

He’s also a rider.

The Glenrock resident said he’s been doing it for 25 years and served as the association’s national president from 2008-2010.

While Bennington has been carrying mail on horseback across the history Pony Express route for a quarter century, the actual Pony Express only operated about 18 months before the transcontinental telegraph made it obsolete.

“I just love the history and I love the horses,” he said.

Bennington said the ride through the state is going well as Cowboy State Daily caught up with him and riders between Glenrock and Casper earlier Friday.

“It’s going better than expected from earlier this morning, but we got it on time from Nebraska. We are staying right on schedule,” he said. “They had a tornado go through Scottsbluff (Nebraska) and we lost some riders there because they had to leave.”

Seven Sections Of Riders

The Wyoming ride is broken into seven sections with a captain and riders for each. Horses are trailered in a mini convoy and each horse and rider cover 2 miles at a lope or gallop before handing the mochilla filled with mail off to the next rider.

And yes, it’s real mail. The ride doesn’t stop, going 24/7 until the mail reaches its destination.

Bennington said the horses that are part of each section will run two to five times during a day, depending on their conditioning.

A GPS tracking device on the mochila allows people from all over the world to follow it from the National Pony Express Association’s web page.

The Casper-area Captain Deidra Homann said she has been doing the re-ride for 13 years. She and the first of the 13 riders under her charge were waiting across from the Sinclair Casper Refining Co. in Evansville to receive the satchel from the Douglas group. Those riders used 20 horses to accomplish their leg of the relay.

“It’s something we look forward to every year,” Homann said. “It’s a reenactment of history. It’s 600-plus riders that have to work together to make it happen. I’ve got a fantastic team and we’ve got a long day ahead of us. We are due in Jeffrey City by 2:15 a.m.”

Homann said riding at night slows down a little. But the horses run better because it is cooler for them as well as the rider. And should clouds cover the moonlight the navigation is just a “confidence between horse and rider.”

For Liddy Chaney, this year’s ride is her 14th. She was the Casper section’s first rider and plans called for her to be the last rider into Jeffrey City.

Chaney said she and Homann also will take a 5-mile section alone across Pathfinder Ranch around midnight. Trucks and trailers are not allowed, so the pair ride together, one with the mochila.

“It is fabulous,” she said. “It is the finest ride on the route.”

  • National Pony Express Association Wyoming President Les Bennington of Glenrock and son, Buck, of Laurel, Montana, prepare a horse for Buck’s ride.
    National Pony Express Association Wyoming President Les Bennington of Glenrock and son, Buck, of Laurel, Montana, prepare a horse for Buck’s ride. (Dale Killingbeck, Cowboy State Daily)
  • Anna Carpenter, 22, of Glenrock, gets on “King” to take the mail down the route. She has participated in the re-ride nine times.
    Anna Carpenter, 22, of Glenrock, gets on “King” to take the mail down the route. She has participated in the re-ride nine times. (Dale Killingbeck, Cowboy State Daily)
  • Liddy Chaney of Casper has participated 14 times in the annual National Pony Express Association re-ride. She enjoys going across Pathfinder Ranch to the southwest of Casper at night. She was the Casper section’s first rider and planned to be its last into Jeffrey City.
    Liddy Chaney of Casper has participated 14 times in the annual National Pony Express Association re-ride. She enjoys going across Pathfinder Ranch to the southwest of Casper at night. She was the Casper section’s first rider and planned to be its last into Jeffrey City. (Dale Killingbeck, Cowboy State Daily)
  • Curt Bennington brings the mail on to the next rider. He’s been doing the re-ride since he was 14 years old.
    Curt Bennington brings the mail on to the next rider. He’s been doing the re-ride since he was 14 years old. (Dale Killingbeck, Cowboy State Daily)
  • The National Pony Express Mochila had a GPS device attached to it and carried about 1,000 pieces of mail. Riders who wanted to could sign it.
    The National Pony Express Mochila had a GPS device attached to it and carried about 1,000 pieces of mail. Riders who wanted to could sign it. (Dale Killingbeck, Cowboy State Daily)
  • Many riders had special vests with the National Pony Express Association logo on the back.
    Many riders had special vests with the National Pony Express Association logo on the back. (Dale Killingbeck, Cowboy State Daily)
  • Rhodi Brow, 17, of Glenrock, enjoyed his first year on the ride and said he enjoyed reliving the history.
    Rhodi Brow, 17, of Glenrock, enjoyed his first year on the ride and said he enjoyed reliving the history. (Dale Killingbeck, Cowboy State Daily)

Enjoying The Ride

Buck Bennington, 48, was accompanying his dad on the annual event. He has been riding since he was 14 and now lives in Laurel, Montana. He also took a turn in the saddle.

“I always tagged along, and when I was old enough to ride, I started riding,” he said. “It’s fun. It’s good to see family and good people and get out and enjoy it.”

Anna Carpenter, 22, of Glenrock is in her ninth year. She was initially encouraged to join the association by Bennington and has experience as a horse jumper in Colorado.

She enjoyed taking the mochila and galloping on a 2-mile run a few times during the day. One of her mounts belongs to Bennington, a former BLM wild mustang he’s named King.

“A lot of people my age really don’t know about the Pony Express, so it’s nice to be able to educate people,” Carpenter said. “And then ride like they did, a little bit shorter length, but like they did.”

Rhodi Brow, 17, was enjoying his first year taking the mochila and galloping his horse Bernie down the side of the road from Glenrock to Casper. Brow said taking the oath of a Pony Express rider was a little nerve-wracking at first.

After all, he’d be really carrying some mail.

“It’s a big responsibility,” he said.

The mochila fits over the saddle of the riders and has four pouches. Bennington said it weighs about 30 pounds. It’s carrying about 1,000 special commemorative letters at $5 each that were submitted by anyone who wanted to be part of the historic event.

Envelopes travel the entire journey and receive a special post mark by the U.S. Postal Service.

The Oath

Riders of the re-ride have to be members of the National Pony Express Association, be at least 14 years old and provide their own mount and tack. All the riders need to wear Western attire. Many had vests with the National Pony Express Association logo.

Every rider participating in the re-ride has to take the oath that original Pony Express riders took:

“I (name), do herby swear, before the great and living God, that during my engagment as a member of the National Pony Express Association Re-Ride, I will under no circumstances use profane language, that I will drink no intoxicating liquors, that I will not quarrel or fight with any member of the Association, and that in every respect, I will conduct myself honestly, be faithful to my duties and so direct my acts as to win the confidence of my associates. So help me God.”

The mochila itself was covered in signatures. Each rider could sign it if they chose.

While riders can be seen along the route across much of the state, they made a special stop at the National Trails Historic Interpretive Center on Friday afternoon. A stop is also planned for Granger Station at 5:30 p.m. Saturday.

The Pony Express was only operated for 18 months starting in 1860 by the the Russel, Majors and Waddell Co. There were 80 riders, 184 stations and ran until the transcontinental telegraph was established. The mail service connected the East with the West.

Authors

DK

Dale Killingbeck

Writer

Killingbeck is glad to be back in journalism after working for 18 years in corporate communications with a health system in northern Michigan. He spent the previous 16 years working for newspapers in western Michigan in various roles.