Riders of Destiny
Area horse enthusiasts deliver
on the Pony Express
Indiana riders carry on tradition
at the Canaan Fall Festival
September 2019 Cover
(September 2019) – When Roger Mills heard about the annual running of the Pony Express Mail Run from Canaan, Ind., to the Madison, Ind. Post Office, 14 miles away, he thought it would be something fun to do. After all, he had plenty of experience in the saddle with his own series of Wild West shows and Civil War re-enactments around Indiana, many times with him and his friends portraying Confederate Gen. John Morgan’s Raiders. He also operates a cowboy camp near Brownstown, Ind., where 70 or so horse owners ride in for campouts and cowboy-style dinners and music.
But it would be several years before Mill’s group took the reins of the Canaan re-enactment Pony Express ride that occurs each September as a highlight of the Canaan Fall Festival.
This year’s festival is set for Sept. 13-14, with the Mail Run swearing in and ride set for 1 p.m. Saturday. It will be the 55th year for the festival and the 53rd years for the Pony Express run to Madison. The festival is organized by the Canaan Restoration Council.
Canaan Fall Festival
Friday, Sept. 13:
5 p.m.: Country Kickers Line & Partner Dancing
7 p.m.: Keith Swinney Band
Saturday, Sept. 14:
10:30 a.m.: Parade
After parade: Kids’ Pedal Pull
Noon & 3 p.m.: Cowboy Posse Old West re-enactment
1 p.m.: Pony Express Mail Run
1:30 p.m.: Kids’ games, Frog Contest
4 p.m.: Cornhole Tournament
7 p.m.: Silver Wings Band
• Free admission
• Presented by the Canaan Restoration Council
• Information: (812) 839-6855 or (812) 839-4600
“I was aware of it years ago but never made it to Canaan to see it,” said Mills, 63, a self-employed carpenter who resides near Scottsburg, Ind. “I was in Madison on day when the riders came through, so I talked to them afterward about doing it with them.” He then contacted Carolyn Hankins, who was then the Canaan postmaster who helped organize the festival. She invited Mills to take part in the ride.
So 10 years ago, Mills donned his period cowboy clothes and saddle and black-powder pistol and trailered his horse to Canaan. He joined the other riders that year and was the only one dressed in period cowboy clothes.
“People were impressed because I looked so much like the real thing,” Mills said.
Soon afterward, Hankins contacted Mills to ask if he had friends to dress up in period cowboy clothing and make the ride each year. Mills and about six others from his group began doing the ride every year, and they’re still doing it. The camp out the night before at a barn in Canaan and have a big cowboy-style dinner.
“I consider it a privilege and a pleasure to do it,” he said. “I’m a little old to be a real Pony Express rider. They were all teenagers or in their 20s.”
But the folks in Canaan are not concerned about their age; they enjoy seeing the colorful cowboys being sworn in at the Canaan Post Office and then riding their horses out of town before taking their turns galloping from point to point across Jefferson County and down the Hwy. 421 hill into Madison. The horses are trailered ahead to each transfer point along the route. Actual mail from Canaan Post Office is carried in the “mochila,” or mailbag draped across the horse’s back and handed off from rider to rider.
Roger Mills’ group of horse riders make the 14-mile trip each year from Canaan to Madison to deliver the U.S. mail.
“We all meet up at the bottom of the hill (at the location of the former Darrell’s Tires) and then ride into town to the post office together,” Mills said. “We get lots of attention from people, and lot of them cheer us on. I get an adrenaline rush every time I do it.”
Mills says his team has the record time of 55 minutes. But like most history connected to the real Pony Express, his claim is among several “records” claimed throughout the history of the Canaan run.
As Jim DeFelice writes in his 2018 book on the Pony Express, “West Like Lightning,” he says “the real story of the Pony Express, like the history of the Old West and America in general, is far more complicate and nuanced than most of us learned in school.”
DeFelice makes several references in his book that getting at the true history of what happened with the Pony Express is undocumented. Even establishing that fact of the man who is considered its first rider, Kentucky-born, 20-year-old Johnny Fry, is really just a good guess. “Because like almost everything connected to the Pony Express, there is no gospel record of the event.
In fact, there’s no way to be absolutely certain he did any run, though there is plenty of testimony to that effect,” DeFelice writes. “The records of the parent company were lost to history, leaving historians to sort through scraps of evidence.”
History of the original Pony Express
The Pony Express began on April 3, 1860, in St. Joseph, Mo., just ahead of the presidential election of Abraham Lincoln in November of that year. In fact, news of Lincoln’s presidential victory was perhaps the most important news carried west by the Pony Express, as noted in DeFelice’s book.
Photo by Don Ward
Ron Bladen of Madison displays his photo album and collectibles from his many Pony Express runs.
A grand ball was held the night before the first ride, and the riders were the toast of the town, DeFelice writes. The next day as the riders prepared to leave at 4 p.m., speeches were made, the mayor predicted great things for service, for the country and most especially for the city. The crowd cheered. Only problem was, the mail arriving by train from Hannibal but had been delayed at Detroit. So the riders did not get off until 7:15 p.m. The riders managed to make up the time to get the mail across the country on schedule.
From St. Joseph, Mo., to Sacramento, Calif., the Pony Express could deliver a letter faster than ever before, according to a short history from the National Pony Express Association, based in Pollock Pines, Calif. In operation for only 18 months between April 1860 and October 1861, the Pony Express nevertheless has become synonymous with the Old West. In the era before electronic communication, the Pony Express was the thread that tied East to West.
As a result of the 1849 Gold Rush, the 1847 Mormon exodus to Utah and thousands who moved west on the Oregon Trail starting in the 1840s, the need for a fast mail service beyond the Rocky Mountains became obvious. The need was partially filled by outfits such as the Butterfield Overland Mail Service starting in 1857 and private carriers in following years.
But when Postmaster Gen. Joseph Holt scaled back overland mail service to California and the central region of the country in 1858, an even greater need for mail arose. The creation of the Central Overland California & Pike’s Peak Express Co. by partners William H. Russell, Alexander Majors and William B. Waddell became the answer. It was later known as the Pony Express.
The 10-day delivery involved 40 riders in the saddle in each direction, 190 stations and 400 station keepers who kept the operation running smoothly. Each rider traveled an average of 50-75 miles, day or night, then handed off the mochila of mail to the next rider and horse for the next leg. Riders were paid $25 a week and rode 10-15 miles before changing horses.
The company hired young, skinny men to ride the Express because they were faster.
Photo by Don Ward
The 2003 Pony Express riders arrive at the Madison, Ind., Post Office with mailbag in hand. It took them 54 minutes. They are (from left) Susan Asher, Sherry Schack, Ron Bladen, Jennifer Babb (Asher) and Robert Jones.
According to the 1966 book “Pony Express” by author Fred Reinfeld, only one rider died on the route, and his horse still made it to the next station with the mail. Conflicts with Native Americans were greatly exaggerated in later year, but the weather posed the greatest obstacle.
The Pony Express was a dramatic attempt by the three business partners to capture a federal mail contract. Although it was not successful, it proved the Central Route as an all-weather transportation route. It is remembered as one of the enduring symbols of the American Frontier.
But 10 weeks after it began operation, Congress authorized a bill to subsidize construction of a transcontinental telegraph line, and when it was completed on Oct. 24, 1861, the Pony Express was done. Adding to its demise was the failure of the company to secure a government mail delivery contract and interference from other conflicts, such as the Paiute War, which disrupted travel across the West.
Historians record that the investors lost about $200,000 and only made $90,000 in revenue. As the National Postal Museum notes, the business lost up to $30 for every letter it carried.
To commemorate its short history, each year in June more than 750 horse riders each take part in the National Pony Express Association’s annual Re-Ride event. During the 10-day period, the riders travel the 1,966-mile original trail through eight states 24 hours a day to deliver about 1,000 letters, which are put in a mochila similar to the ones carried in the 1860s. The association was incorporated in 1978 as a nonprofit, historical organization “with the purpose of identifying, re-establishing and marking the original Pony Express National Historic Trail from St. Joseph, Mo., via Kansas, Nebraska, Colorado, Wyoming, Utah to Sacramento, Calif.”
Today, the contributions of the original Pony Express to the development of communications in the west are commemorated by the Pony Express National Historic Trail. Legislation authorizing the addition of the trail to the National Trails System was signed by President George W. Bush on Aug. 3, 1992. It is administered by the National Park Service.
Canaan’s Pony Express Mail Run origins
Canaan’s Mail Run began in 1967 with then 22-year-old Canaan resident Louis Griffin as a solo rider taking the reins. Similar to today’s ride, he took the back roads across Bacon Ridge and down the hill into Madison. He had no law enforcement escort like the riders do now.
Contacted at his home in Tennessee in August, the now 74-year-old Griffin said he used six horses to make the 14-mile journey from post office to post office and rode each horse about two miles. He had friends and neighbors waiting at each stop with a replacement horse.
A Canaan resident loaned Griffin a Western vintage outfit to wear. He said the clothing was more than 100 years old at the time. Griffin said he completed the run in about 60 minutes. Griffin made the solo trip again in 1969.
The second year, a stagecoach, driven by Elbert Hartman, was used. Every year since, the mail has been carried by experienced horseback riders. Dave Singer and Ron Day were other early riders who made the trip, sometimes as a solo rider, for six years each. Singer’s rides took place between 1973-1983, and Day’s between 1987-2000.
The Mail Run was overseen by former Canaan postmasters Bessie Wolf, Neida Rogers, Minnie “Daisy” Kessler and Hankins, who in 2014 moved on to the Versailles, Ind., post office before retiring in 2016. The Canaan post office is not under the direction of the Madison postmaster, Anita Parks, with a clerk working at the Canaan location.
In later years, the Clifty Creek Saddle Club provided riders to conduct the ride. Ron Bladen of Madison was among those club members who carried the mail on horseback for four years – 2000, 2001, 2003 and 2008.
Each year, the post office receives hundreds of letters and post cards from all over the world to be included in this popular tradition. Some letters come from as far away as China, Germany and Japan, Hankins said in a 2004 RoundAbout article. Each piece of mail is postmarked with the hand-stamped pictorial cancellation stamp.
“It’s a humbling and exciting experience,” said Bladen, 58, who owns and operates Suntime Printing in Madison. “I remember the crowd was really into it. They all came out and waved, especially when we got to downtown Madison. The post office was great and even the farmers, who let us park our horse trailers in their pasture.”
Bladen said it was usually very hot in early September while galloping his horse on the pavement. “The people brought us water; the people are really nice out there in Canaan.”
Bladen said he still tries to attend the festival each year and proudly adds, “I still have the horse I rode the last year.” He has a large collection of framed certificates from his rides and large scrapbook of photos from those days that he cherishes.
Also over the years the Canaan Restoration Council and the Canaan community banded together to publish three recipe books that includes photos and history of the Pony Express run. The book lists all the riders through the years up to 2007. The third and final printing was in 2008.
“Everyone enjoys watching the swearing in ceremony and then seeing the horses ride out of town,” said current Canaan Restoration Council President Jeffrey Lockridge. “We have a lot of community pride in the event.”
Nanci Liles, a retired elementary school teacher and 30-year Council member, said, “It’s such a unique event, and we are the only such event east of the Mississippi, so it’s a very historic moment – especially for the children to see how mail was delivered back then. There’s such a majestic feel to see those horses and riders, and they take a lot of pride in doing it.”
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