CROSS-COUNTRY ANTIQUES: INAUGURAL TRANSAMERICAN MOTORCYCLE ENDURANCE RUN

Really nervous. That’s how Kelsey Jackson felt when riders launched their antique motorcycles down the twisting two-lane blacktop on September 4, 2025, from Jennette’s Pier in Nags Head, North Carolina, on the first leg of the inaugural TransAmerican Motorcycle Endurance Run. While hoping the event would be fun for all involved, she was also stressed people wouldn’t show up in the small towns and villages where ‘cyclists would stop for layovers. Prior to the event, “I worked with each community and got press releases out and worked with either the visitor bureau or Chamber of Commerce, and sent out flyers and social media blasts to encourage folks to turn out, even if they’re not motorcyclists,” Kelsey said. “I must tell you I was really nervous because I’ve never done this before. I’m a digital media girl, and I have written tons of press releases, but working with towns and communities was new to me. When we pulled into our first town, which was Apex, North Carolina, there were actually people there and I was like, ‘Oh, thank God!’, because I was worried no one would show up.”

Bryan Bossier of Sinless Cycles aboard his 1923 Henderson DeLuxe, one of three machines he entered in the Transam.  Bryan sponsored two previous Vintagent/Revival Cycles/Sinless Cycles rides on the Motorcycle Cannonball, in 2014 and 2018. Here he rides with the Wolfpack, all on 4-cylinder Hendersons, including Frank Westfall, Loring Hill, Mark Hill, Pat Murphy, Jeff Tiernan, Mike Badlam, and Joe Doelger. [Olivier Touron]
Eager to see antique motorcycles continue to cruise across America in a test of endurance for machines and riders alike, in 2024 Kelsey and Sean Jackson and their business partner Tom Banks began spit-balling ideas about how they could make that happen. Four years ago, Tom, Sean and Kelsey took over Lonnie Isam’s antique parts and accessories company, Competition Distributing. Passionate about pre-1936 motorcycles, Lonnie collected, restored and rode old Harley-Davidsons, and in 1968 turned his love for the hobby into a career that eventually included his son, the late Lonnie Jr., who in 2010 spearheaded the first Motorcycle Cannonball. In 2021, Lonnie Sr. passed Competition Distributing to the Pennsylvania-based trio.

The long and at times lonely road on an old bike going cross-country. Any way you slice it, crossing the USA means 5 days of relatively flat monoculture farming, mostly corn and soybeans, with some amaranth thrown in for color, and occasionally wheat. While most back roads have some curves even in the vast Midwest plains, there’s a lot of seemingly endless riding between the crops. [Olivier Touron]
“Sean and Tom are both busy, but we talked through what we wanted an event to look like,” Kelsey explains. “And they basically said, ‘Kelsey, if you want to take this over, it’s yours.’ I thought it sounded great and was something I could do. We really wanted to get communities involved so people would come out and see these rolling pieces of history, because that’s what these bikes are and they’re usually static in museums. The communities, the riders, the crews, we all wanted everyone to feel special and ensure they were having a good time, and that was really our focus during the starting discussions.” Those initial discussion took place in June 2024, and the trio had just over a year to pull it all together.

Setting off in the morning is always exciting, and occasionally nervy, when you’re praying a known issue with your bike won’t end your rally. But, since these cross-country antique motorcycle rides have been going since 2010, there’s accumulated wisdom on what works, and what mods to make to ensure a steady ride. [Kazuo Matsumoto]
One of the largest undertakings was mapping out a route. Sean roughed it out on a map, and then in a van, when he and Tom drove across the country for a test run. They were working to find compatible mapping software for the phone and computer and were dead set against traveling on any major highways. “Some of these bikes only go 35mph,” Kelsey says, “so we did not get on any fast-moving highways, which was really cool. Sean roughed it in, drove it with Tom, then came home and tweaked it a little bit.” In the fall of 2024, Sean and Tom drove the route and then drove it again in June 2025. The pair drove it again three weeks before the event and found a few road closures that needed to be reflected on the maps. It was a major undertaking. Kelsey says, “That took a lot of time to prepare, and it’s a turn-by-turn paper map in a roller. You use your odometer and total mileage to navigate the route.” On the run itself, there was only a single route change and that was discovered by the daily ‘scout’ who rode ahead of the pack on a Harley-Davidson FXR. Kevin O’Neal left each morning at 5 a.m. on his FXR, and reported back via his daughter, Bryce, who travelled in the van while Kelsey drove. “Bryce would write it all down,” Kelsey says. “Then we’d pull over and then text everybody, and kind of go from there – and there was only that one big change.”

It took many scouting trips over the actual rally route to make an accurate rally guide. Every rider was required to attach a rally map holder on their handlebars. While the roller map was updated only a week prior to the event, there are always unexpected road closures and changes to deal with. [Kazuo Matsumoto]
Kelsey likes to ride and started about 15 years ago on a scooter; she switched to motorcycles about six years ago. Currently, she’s rolling a modern 124cc single-cylinder Honda Monkey for its reliability down the road and also rides a 1970 Shovelhead. “On the Monkey, I can go 60 mph, and I keep up with all the antiques. Sean is building me a JD chopper, but that’s not going to be finished for a year or so. They do like me to ride with them because they might break down, and I’m never going to break down on the Monkey,” Kelsey laughs. It’s that appreciation for antique motorcycles, though, that allowed the team, including nine volunteers, to create an event for 100-year-old motorcycles that everyone enjoyed. Riders paid a $3,500 entry fee, which covered some of the organizing crew’s time in laying out the route, dinner each night and other expenses. For the first run, there were 33 registered riders. The event was capped at 75, but that lower number may have been a blessing in disguise. “It really built up the camaraderie between the riders, and it also gave us, who are new to this, a little more leeway to figure this all out,” Kelsey says.

Norm Berg attends his 1925 Harley-Davidson Model J on the inevitable late-night wrenching session. [Kazuo Matsumoto]
After Apex, North Carolina, Motorcycle TransAm riders found their way to Wheels Through Time Museum in Maggie Valley, NC. The fourth stage ended at Columbia Motor Alley in Tennessee, followed by routes through Missouri, Kansas, Colorado, Utah, Idaho and then Oregon before ending at Heceta Head Lighthouse in Florence, OR. Riders and machines were diverse. “The ride is all about people and motorcycles,” Kelsey says, “and they made the event.” The oldest machine on the inaugural endurance run was a 1910 Thor with Kat Diamond at the controls. Her husband, Mitsuhiro “Kiyo” Kiyonaga, rode a 1919 Excelsior.  Originally from Japan, Kiyo came to America in 2001 and worked at Garage Company. In 2012, he branched out on his own with Kat and opened Kiyo’s Garage. The couple hold several land speed racing records, and Kiyo is a meticulous and creative builder.

A stop at Legends Motorcycles in Springville Utah [Olivier Touron]
“We had two Italian riders, who were really fun and always gave everyone a laugh, and they took their time going across and wanted to see all of the sights,” Kelsey says. “Both of them made every mile, Samuele Reali on a 1924 Indian and Luca Geron on a 1925 Harley JD. They were always positive and having a great time, even when they were working on their bikes really late at night – they were fantastic.” Bill Page rode a 1925 JD fitted with a sidecar and his adult daughter, Amy, was along for the adventure. Kelsey says, “It was really fun to see, and I think that sidecar gave him more problems than he was expecting, but they made all but two days. He went through a couple of clutches, his original rocker tower exploded, his distributor coil went bad, his points went bad, his condenser went bad, his battery went bad, he had six broken spokes in his rear wheel, he sheared off all the bolts of his rear sprocket, and he had a clogged fuel line. Those are just some of the challenges he faced. But they persevered and kept going, fixing most of those problems on the road and finishing in 13th position.” Total milage was 3,714, and they traveled 3405.54 of those miles in the hack.

Kiyo and Kat celebrating the end of the Transam with some Pacific Ocean water. [Kazuo Matsumoto]
There was also the Wolfpack, “who were a lot of fun, and they were all on 4-cylinder machines – four Hendersons and one Ace. We had Bryan Bossier, Pat Murphy, Frank Westfall, Loring Hill and Jeff Tiernan. Jeff was on a 1924 Ace, and while his bike was pretty reliable, there was one setback when his camhsaft broke in half. A replacement cam from 4th Coast Fours was flown in, and it arrived at 2:30 a.m. The Ace was back together by 4:30 a.m., and Jeff missed only a few miles.” Awards went to Mike Butts, who was a member of Team Butts with his brother Larry, stepdaughter Brianna Meisinger, Jerry Wieland and Scott Bernardson. They had a large support crew, Kelsey says, who’d help anyone who asked, and were the only team with a welder. Mike was First on his 1913 Henderson. Second place was earned by Frank Westfall on his ’14 Henderson Model C, and Third was Erik Bahl on a 1915 Harley-Davidson 11F.

Well, it was a competition after all. Here Kelsey Jackson stands with Mike Butts and his team, who won overall with his 1913 Henderson. [Kazuo Matsumoto]
Going forward, the TransAmerican Motorcycle Endurance Run will run every second year. “We were really excited about how well the event went,” Kelsey sums up. “Everyone got along well, and it was successful in the fact the bikes all got across America, and everyone was safe. Also, the community involvement was terrific and the whole spirit of the event was outstanding. Everyone had a really great time and were looking forward to 2027, and registration (https://motorcycletransam.com/) is now open.” For that TransAmerican Motorcycle Endurance Run, machines from 1929 and earlier will be eligible to partake. Get out there and find a project, or complete the one that’s on the bench in the shop.

The end of the road; celebrating the finish [Kazuo Matsumoto]
Mitsuhiro “Kiyo” Kiyonaga on the start line with his 1919 Excelsior. [Kazuo Matsumoto]
The inevitable roadside wrench session. Must have been a very quiet road indeed, given how the bikes are parked! [Kazuo Matsumoto]
If you’ve never crossed the USA on back roads, you haven’t seen the country. [Olivier Touron]
Bill Page and Amy Krueger aboard their 1925 Harley-Davidson JD with a sidecar, the only sidecar outfit on the Transam. [Olivier Touron]
Like the mail, neither rain nor sleet nor snow will stop the riders. [Olivier Touron]
 

 

Greg Williams is Profiles Editor for The Vintagent. He’s a motorcycle writer and publisher based in Calgary who contributes the Pulp Non-Fiction column to The Antique Motorcycle and regular feature stories to Motorcycle Classics. He is proud to reprint the Second and Seventh Editions of J.B. Nicholson’s Modern Motorcycle Mechanics series. Follow him on Instagram, and explore all his articles for The Vintagent here.

 

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