For most of the entrants, the 2010 Motorcycle Cannonball ride will be a once-in-a-lifetime experience. But for Frank Westfall of Syracuse, New York, it’ll be more like old times.

Twice in the past, Westfall competed in The Great Race, a cross-country competition for all types of motor vehicles over 45 years old. Riding a four-cylinder 1928 Henderson DeLuxe, Westfall was aboard one of the few motorcycles to go head to head against the cars that dominated the event. And for his second Great Race in 1998, he even tackled the 4,000-mile course with a passenger, Peg Barber.

Westfall and Barber had a great run in that ’98 event, remaining competitive with the cars despite having to fight through deep snow in Colorado, performing an overnight engine overhaul in a motel room, and then replacing the valves and springs during the race’s one day off. But on the final day, torrential rain worked its way through a crack in the Henderson’s magneto, stranding the machine only 50 miles from the finish.

That experience gives Westfall a unique perspective on the Motorcycle Cannonball ride. And he notes that if anything, this year’s ride will be harder, for both him and the 1915 Henderson Four he’ll be aboard.

“When I did The Great Race, I was 12 years younger, riding a bike 13 years newer,” he says. “It was a challenge in ’98, but this will be even tougher.”

Westfall’s experience has taught him that both halves of the equation—the bike and the rider—need to be in perfect condition to tackle a cross-country ride.

“You’re talking about motorcycles that are almost 100 years old,” he says. “These things are frail—very frail. In the case of my Henderson, the flywheel is small and so is the clutch. Plus, you have the limitations of the metallurgy back then. There’s a big difference, even between a ’20s motorcycle like I rode the last time and a teens bike like this. Knowing those limitations is everything.

“They’re really pushing the limits with this ride. We’re doing a continental crossing that took months back then, and we’re going to do it in a couple of weeks. Granted, we’ve got better roads, but it’s the same bikes, with the same metallurgy. We’ll be pushing the limits of these machines.”Westfall will be riding with other single-speed twins and fours in Class 2. And he expects the lack of a transmission to be the biggest challenge facing him and other Class 2 competitors.

“The guys with the ’15 Harleys with the three-speed transmissions (who will compete in Class 3) are going to be the kings of the road,” he predicts. “When it comes to hills, a three-speed transmission will be great. For those of us on the single-speeds and the belt drives, it’s going to be a big challenge for the machine and the rider.”

Westfall says he plans to prepare himself for that challenge with regular workouts.

“I know that I may have to walk the bike up some of the hills—even if the hill is seven miles long,” he notes. “If it’s the difference between blowing me up or blowing the bike up, I better go to the gym.”

But beyond those specific challenges, Westfall notes that riders will have to hold up to the abuse of long days aboard a constantly vibrating machine.

“It may not seem like much of a problem if you ride for a few hours,” he says. “But it’s like taking an egg and holding it in your hand and shaking it and shaking it, hour after hour, for days. How long is that egg going to hold up?

“You’re going to have to work through aches and pains. In ’98, I blew a leg muscle and I couldn’t even put my boot on for a few days. You have to find ways to work through it all.”

On top of that, Westfall notes that the main enemy of all Cannonball riders will be Murphy’s Law.

“At any given moment, something can go wrong,” he says. “The variables are unlimited, so there’s no way to prepare for everything. It all comes down to how well you can react when the inevitable happens.”

In an effort to be ready for anything, Westfall is starting with a few bike modifications, including quality brakes, front and rear. For his Great Race journeys, he mounted a massive disc brake on the front of his ’28 Henderson, and he’s still working on a system for the ’15 this year. Plus, he’s making changes designed to improve the bike’s comfort level for long days, including repositioning the stock running boards, which are located far forward, to a spot underneath his riding position.

“I’m also trying to figure out what kind of handlebars I want to run,” he says. “I’ve had carpal-tunnel syndrome, so I need to get that part right.”

Beyond that, he’s looking for ways to haul plenty of spare parts and tools on the machine with him.

“I’m going to make the biggest set of saddlebags I can, and load them with all the standard stuff—valve springs, magneto, carburetor,” he says. “Plus, I’ll have even more stuff on the support truck: cylinders, rods, pistons, valves—maybe even a whole spare motor. You’ve got to be a Boy Scout and be prepared.”

In spite of all the challenges between now and September 26, when the Cannonball ride arrives at its destination in Santa Monica, California, Westfall says he wouldn’t miss it.

“When I first heard about this,” he says, “ I thought, ‘What, they’re having a party without me?’ This is too good an opportunity to pass up.

“Plus, the gentleman who’s laying out the course, John Classen, is, I think, one of the world’s great rally masters. And I’m looking forward to the route he’s going to have for us.”