Following one of his mining expeditions in 1901, Tilden hiked from El Dorado County to the town of Colfax in Placer County, one of his stopovers in the Sierra foothills. As he awaited the westbound Southern Pacific Overland Limited to San Francisco, he noticed a man on the rail platform passing out handbills. A club in Ogden, Utah, was sponsoring a contest: the first traveler to make his way from Ogden to San Francisco with but a meal’s worth of coins in his pocket would win $500 (the equivalent of nearly $18,000 today!).

Though the name of the Ogden club is not known and the rules of the wager are vague, the contestants were to pay no fare whatsoever to reach San Francisco. How the winner would prove he neither acquired money along the way nor paid for transportation is anyone’s guess. If this story sounds like something out of the old Wild West, well, it is, and Tilden took the bait.

It was a circuitous route traveling east to Utah before heading home to California, but a diversion he could not resist. With a predisposition for spontaneity, daring, and discovery, Tilden climbed aboard an eastbound freight in Colfax, carrying with him his ubiquitous sketch box, and train-hopped 650 miles to Ogden. By the time he arrived at the Union Station, dozens of fortune hunters had gathered. With no chance to rest, he registered for the contest, downed a quick meal, glanced at the giant clock tower, then tramped aboard the ensuing westbound freight, dreaming of the prize awaiting the first voyager to cross the finish line in San Francisco.

After miles of rail travel from Utah across Nevada to Reno, the ascent over Donner Pass in the Sierra lay some hours ahead. But as the Overland pulled into the station in Reno, Tilden, weary and hungry, leapt from the freight and climbed atop the nearest barn loft in the railyard.

There he encountered a man stretched out in the hay writing in his notebook.

Thus begins the story of how Tilden Daken first met Jack London atop a haystack. London would soon become internationally famous, recognized for his literary and journalistic accomplishments including 50 fiction and nonfiction books. Two decades later, Tilden would relate this encounter to Louise M. O’Hara, feature writer and art critic for the San Francisco Call and Post.” Tilden’s subsequent friendship with London, and the writer’s premature death in 1916, “had thrown the artist into a reminiscent mood,” wrote O’Hara. The artist recalled:

As I swung into the barn loft, I saw a man sitting on the hay. He looked me over with friendly curiosity. “Is there room here for another lodger?” I enquired. With a gesture, he offered the hospitality of the loft and we were soon exchanging conversation of the road, including the terms of my wager.

 “By the way, are you a painter?” London asked with a glance at my sketch box.

“Yes, I’m Tilden Dakin,” I said. “And you are a—writer?” I returned, looking at the pad and pencil on the hay by his side.

“I’m Jack London,” he replied, scrambling to his feet, “and as hungry as the deuce. I must get out and find something to eat.”

“Well, don’t go hungry. Here’s my 30 cents,” I said, offering my all.

In a short time, he returned with a bulging paper bag and held out to me 15 cents. “Snails and doughnuts,” he explained. “They’ll do me until I reach Truckee.”

Born within months of one another in 1876, London in January and Tilden in June, the painter and the writer, both 25 at the time, hit it off straight away. While it is not known where London’s journey had originated, he was making his way to Oakland, and Tilden was heading across the Bay to San Francisco.

The westbound train was scheduled to arrive the following morning. That night, in the Reno railyard, London taught Tilden his rules of the road, the precarious practice of clinging to the brake beams inches above the track, or in the hobo vernacular, “riding the rods.”

At noon the next day, the Overland Limited pulled out of the Reno station carrying with it two passengers lying on the rods. Little more than an hour later, the train pulled into Truckee, the lumber town near Lake Tahoe that sprang from the Gold Rush. The newfound friends jumped from their berth, breakfasted in town on the remainder of Tilden’s 15 cents, and secured temporary work in a lumber mill. Tilden continued his story:

Handling the green timber was hard on London, so after a day’s work, enough to buy food, we asked our time. When the superintendent heard our names, he said he would have advanced funds without our working for them and tried to force a $5 bill on me. I told him of my wager and asked that he give me just the $2.75 that was due me and add the remaining to London’s account.

So, feeling like plutocrats, we boarded a freight bound for the Summit. It was a cold ride at this season of the year, but we hugged the brake boards, which keep pretty warm over the wheels. Jack was a great fellow to ride the rods and when traveling always carried a padded board for the purpose, but this trip he kept close to the brakes.

As the train approached Donner Pass, the writer and the artist clung tightly to the underbelly. “Passing through [the] summit, when the train reached Blue Canyon, the travelers were ordered off the train by the conductor,” wrote O’Hara, meaning the ever-watchful brakemen, or “shacks” in the lingo, who endlessly pursued the tramps.

“But [London and Dakin] watched [for] their chance and as it gained momentum [they] leaped to their ‘berths’ again.” O’Hara’s article continued:

According to the rules of his wager, Dakin was to pay no fare whatever to reach San Francisco. His only difficulty lay in the ferry at Benicia with its gang of watchmen. But as the train was broken up and shifted, London, to whom this mode of travel was an old thing, guided Dakin in between the locomotive and onto the brakes again. An hour or two later, they rolled into the Sixteenth Street station in Oakland, and Daken, giving London a good hand grip, beat his way into San Francisco and won his $500 wager.

“London had a big heart,” Tilden told O’Hara, finishing his story, “too big a heart for his own good. . . . And our notes—I worked mine into several canvases and you’ll find Jack’s developed in some of his stories of those days.”

Six years late, London would publish The Road (1907), his 19th publication, a memoir about his years riding the rails. Though his adventure with Tilden is not mentioned—he was, after all, a painter not a tramp—London wrote of the fellow hobos he met along the way, his aptitude for avoiding the dreaded shacks, and his ability to escape death while riding on the brake beams.

A few months after the San Francisco Call and Post published the December 1921 story of Tilden and London’s brake beam adventure, Tilden mailed a clipping of the article to Louis W. Hill, president and board chairman of the Great Northern Railway. On the surface, it is unclear why Tilden chose to send the article to Mr. Hill, as he and London were not stowaways on the Great Northern Railway from St. Paul to Seattle, but rather they rode on the Southern Pacific Railway from Ogden to Reno to Truckee to Oakland. Nonetheless, believing he owed the railroad executive an apology for his transgression, on the face of the article Tilden wrote: “Mr. Hill, I did not intent [sic] to beat the rail fare, but I needed the $500.”

Tilden, too, had a big heart.

This is an excerpt from The Man Beneath the Paint: California Impressionist Tilden Daken by Bonnie Portnoy. It’s published here with permission.

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