Riding the ‘Cannonball’: A 3,700-mile endurance race on the back of a 90-year-old motorcycle

Gorilla tape and baling wire.

That’s what held together Jeff McAllister’s 1927 Indian Big Chief motorcycle as it dripped gasoline onto the hot engine thousands of miles from home.

For the 62-year-old Ridgefield resident in the saddle of this dubious machine, the solution was obvious — twist the bike’s weird, left-handed throttle, and pray the air whipping past the 90-year-old motorcycle blew the gas away before it caught fire.

McAllister survived that mishap — and many more — on a 3,750-mile journey from Portland Maine, to Stevenson, Wash., as part of the the Motorcycle Cannonball, an annual “endurance race” that saw 107 entrants ride across the USA this year on machines that would have been considered antiques in their grandfathers’ day.

The route is almost all backroads, with minimal time — less than 11 miles, according to the event’s website — spent on the highway slab.

“To see America on all backroads is incredible,” said McAllister. “You’re seeing the real grit of America” — fewer chain restaurants, and more boarded-up signs on Main Street.

The Cannonball followed a northern route across the continent, with 14 stops before the big finish in the Evergreen State. It took about two weeks, with the riders thundering out of Maine on Sept. 8, and rolling into Stevenson on Sept. 23.

McAllister’s wife, Stacy, rode on the back of the 1927 Indian Big Chief for part of the trip. She was going to join him for one leg that led through Glacier National Park, but snow on the forecast made her skip that part of the journey.

His friend Denis Sharon — a former Ridgefielder who now lives in New Milford — also competed in the Cannonball on a 1916 Harley Davidson, until a seized engine forced him to drop out.

On a recent visit to McAllister’s home off North Salem Road, he showed off a collection of about a dozen motorcycles that have a winter home in his garage. Most are British and Italian bikes from the 60’s and 70’s — the Indian he rode in the Cannonball is by far the oldest in his collection.

Right now the bike is up on a lift for the winter. McAllister plans to pull the engine off the frame for cleaning and repair.

Despite riding a bike that rolled off the assembly line during the Coolidge administration, McAllister said the bike was smooth enough there were times it felt like he was riding a modern Harley Davidson.

He’s planning to keep the Indian for the next Cannonball in the hopes that it qualifies. Two years ago, he said, the entry rules mandated that entrants ride a bike at least a century old. If that happens, he plans to sell the Chief.

Rules of the road

Under the rules of the event, everyone who entered had to make the journey riding a motorcycle from 1929 or earlier. That included everything from McAllister’s Indian — a more-powerful bike once intended to tow a sidecar — to the Nera car, a “nearly-a-car” contraption from 1923 that wheezed along on a two-horsepower motor.

It’s less a test of speed, and more a question of endurance and mechanical Macgyver-ing by the roadside. Riders gain points for every mile they travel between stops on their bike, with chase trucks to pick up anyone whose bike seriously broke down.

The somewhat arcane rules of the “race” meant that entrants gained points not just for the stages that they completed, but also for the age of the bike, age of the rider, and how underpowered their machine was.

A 104-year-old Harley Davidson with a leather belt driving the rear wheel claimed the top prize. The rider, Dean Bordigioni of Santa Rosa, Calif., had to push it up every hill, McAllister said.

“It was a three-mile hill up Mount Rushmore, but he did it,” he recalled.

Other notable entrants included the Japanese-born, custom-motorcycle builder Shinya Kimura, and land speed record-holder Jody Perewitz — a native of Halifax, Mass.

As for McAllister’s favorite spot on the journey?

The “breathtaking” dry scrub-desert of Walla Walla, Wash. — famous for its sweet onions.

Safety first

The only serious accident came when a father-son team collided at a traffic stop.

The dad “plowed” into his son, McAllister recalled. “They both went off the road and he broke ribs. He was pretty banged up, the son was okay… And only one bike was rideable after that.”

Many of the riders wore period-era motorcycle clothing — tall leather boots, canvas breeches, and leather jackets — but plenty of others opted for modern helmets and safety gear. At a bare-minimum, McAllister said, the bikes had to have horns and mirrors as safety items — which were often dealer options at the time the bikes were built.

A 30-year resident of Ridgefield, McAllister said he got into motorcycles as a teenager growing up in the Shippan Point neighborhood of Stamford. Mom wasn’t thrilled, but she eventually caved and gifted him a fluorescent-orange helmet for Christmas.

“She said ‘I know I can’t break this habit, but just put this stupid thing on your head,’” he said with a laugh.

When he’s not riding cross country, McAllister works as a harbor pilot offloading ships in New York City.

Breakdowns and mishaps

“The chief that I rode is a pretty rare model, there aren’t that many in the U.S.,” McAllister said. He bought the bike from a collector in the Netherlands ahead of the race. It gave him some trouble early on — “the engine was in pieces two days before the start,” he recalled.

Because of that, he said, he didn’t have the rest of the bike up to snuff by the start of the race — which he found out when gas started leaking from the tank. It would become a constant issue on the road, with Sharon eventually re-soldering the tank together when the group arrived at Sturgis, S.D. Or, as McAllister put it, his friend deserved thanks and credit for “nursing me across the country.”

He usually spent about three hours every night fixing something on the Chief.

At times, riding along forgotten backroads in the prairie heartland, the group couldn’t see any other signs of human existence as far as the horizon. The family farmhouse that once dotted the landscape had been torn down by corporate farms, leaving miles of farmland sweeping in the wind.

Most of the bikes were happy at around 45 to 50 miles-an-hour, Mcallister said. Any more would push the motors to the breaking point.  

“It’s a little more of an adventure-pioneer spirit,” he said. “You’re on your own.”