In the annals of motorcycle history, there are journeys that become legends and travelers who turn into heroes of their own epics. Among these tales, the story of Diego Roson echoes with a unique melody of adventure and rekindled dreams. At 55, Diego embarked on a journey many only dare to dream of: traversing the Americas from tip to tip, from Ushuaia at the southern end to distant Alaska. This narrative begins with the first leg of his odyssey, a journey from La Quiaca to Ushuaia, aboard a faithful Royal Enfield Classic 500.

Diego, an Argentine with a spirit as free as the vast routes he traverses, finds inspiration in the words of Jack Kerouac: “The only people I’m interested in are the mad ones, the ones who are mad to live, mad to talk, mad to be saved, desirous of everything at the same time, the ones who never yawn or say a commonplace thing, but burn, burn like fabulous yellow roman candles exploding like spiders across the stars.” This sentiment, from On the Road (1957), encapsulates the essence of Diego’s journey and his life. Echoing the freedom of the 60s, his daughter Martina affectionately calls him “Hippie”, a nickname he proudly embraces, reflecting his longing for freedom and adventure.

Ushuaia to La Quiaca

The Unexpected Beginning of a Northbound Dream

Diego Roson’s journey, though destined from Ushuaia to Alaska, took an unexpected turn right from the start. Due to logistical factors, what was originally planned from Ushuaia to La Quiaca had to be reversed, beginning a northbound adventure filled with unforeseen experiences and challenges.

Diego’s odyssey truly began in a moment of quiet introspection, long before the engine’s roar marked the start of his physical journey. As he slid back the truck’s tarp in La Quiaca, his eyes fell upon his motorcycle, waiting patiently in the shadows. It was a poignant revelation, a tangible symbol that his long-held dream was about to unfold. “Our dream was starting,” he reflected, a mix of awe and excitement in his voice.

Preparing for the road, Diego and his lifelong friend Willy underestimated the task of packing their gear. Under the scorching morning sun of San Salvador de Jujuy, they scrambled to organize their belongings, a task that would later necessitate several stops for re-adjustments and balance checks. It was a humble commencement, marked by laughter and the subtle, teasing spirit of Diego’s late father. A man who had lived with the soul of a Daniel Boone, he had instilled in his son an unquenchable thirst for adventure. His father’s spirit, laughing gently on his shoulder, seemed to revel in the early moments of the trip, amused by the rookie mistakes of the first few miles.

As dawn’s first light crept over the horizon, Diego and Willy embarked on the inaugural leg of their adventure, which they had fondly named “Monos on the Road.” Their journey commenced with an early departure from La Quiaca, marking the beginning of what promised to be an unforgettable story. The town, silent and deserted at 7:00 AM, offered a tranquil backdrop as they began their ride. In keeping with a road-tripper’s tradition, they proudly affixed their “Monos on the Road” sticker onto a route sign, marking their passage and joining a community of travelers who had passed before them.

As they left La Quiaca under a brooding black cloud casting its shadow over the mountain range, a sense of suspense enveloped the early kilometers. Unprepared for a sudden storm, they were caught off-guard and drenched, the combination of their wet clothes and the chilly 52°F (11°C) weather sending shivers to their bones.

Their first noteworthy pause came when they spotted an abandoned bus in a field, evoking scenes from ‘Into the Wild.’ Compelled to capture the moment, they briefly felt as though they were part of a grand adventure akin to the movie.

Their journey through the Northern Argentine landscape was a revelation. Diego was astonished by its beauty, stopping countless times to take photos. Each stop was a reminder of his misplaced glasses, a humorous nuisance that he vowed to address urgently.

The day’s journey took an exhilarating turn as they approached the Cuesta de Lipán. This stretch, akin to an amusement park for motorcyclists, offered hundreds of curves leading up to the day’s highest point at 13,681 feet (4170 meters) above sea level. The descent from this peak was equally thrilling, leading them towards the Salinas Grandes, an expansive, otherworldly landscape of endless white salt flats.

A fortunate encounter allowed them an incredible two-hour ride across the salt flat. However, their indulgence in the beauty of Salinas Grandes meant a delayed departure towards Susques. The rough gravel roads of Ruta 40 presented them with striking landscapes, small indigenous villages, and herds of animals, but also the frustration of losing, and then retrieving, their GoPro camera.

Their day culminated with a late arrival at the Viaducto La Polvorilla, part of the famous Tren de las Nubes (Train of the Clouds). The sun was setting, leaving them little time to admire this engineering marvel. Nightfall caught them off guard, compelling them to break their promise of not riding in the dark and pushing them to continue to San Antonio de los Cobres, seeking the warmth of a bed over the cold prospect of setting up camp in 37°F (3°C) weather.

Close-up of Ducati DesertX Rally's high front mudguard and wheel.

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On the second day, after covering a distance of 300 miles (484 km), Diego, Willy, and their Royal Enfield Classic 500s faced challenges that tested their endurance. The journey through rugged landscapes and unforeseen obstacles pushed them to their limits, forging a bond between man and machine that was unbreakable. After a night in the rustic setting of San Antonio de los Cobres, they started the day with routine bike maintenance, preparing for the challenging route ahead.

A change of plans led Diego and Willy to explore the captivating Quebrada de las Conchas. This detour, nestled between Cafayate and the city of Salta, offered a breathtaking landscape that was almost otherworldly in its beauty.

Diego described this part of the journey in his book, saying, “The Quebrada de las Conchas was like stepping onto another planet. Every turn revealed a landscape more astonishing than the last, a vivid tapestry of nature’s artistry.”

After capturing the beauty of the Quebrada in photographs and memories, they retraced their steps towards their final destination for the day, Chilecito. The ride was a mix of quaint towns and open roads, leading them eventually to the vast, seemingly endless desert. This stretch, characterized by a perfect straight line cutting through the heart of the desert, was a test of endurance and focus.

Diego noted, “Two hours of straight riding in the desert’s unyielding heat, with nothing but the occasional wild goat or donkey for company. It was both a meditation and a challenge.”

Their journey took them through Belén, where they paused to capture a photo at the iconic Ruta 40 sign at Km 4040. They then passed through Londres, paying homage to the origin of their Royal Enfield bikes, and explored the ruins of Shincal. Here, they took a break for bike maintenance and hydration, with the desert’s intense heat making its presence felt. On this leg of the adventure, they managed to traverse a distance of 294 miles (474 km).

The fourth stage of their odyssey, though planned as a shorter 151 mile (244km) stretch, unexpectedly blossomed into a day brimming with adventure. Each turn in the road revealed new challenges and wonders, transforming what was meant to be a brief journey into a full day of exploration and discovery. Leaving Chilecito, Diego and Willy encountered a fellow motorcyclist, Rubén from Formosa, who was also on his way to Ushuaia. They learned about the upcoming International Travelers Meeting on November 29th and 30th – an event that reinvigorated their spirits and added a new goal to their itinerary.

Diego reminisces in his book, “Meeting Rubén was a reminder of the camaraderie that exists among those of us who embrace the road. His story, much like ours, was written one mile at a time.”

Their route took them through the Cuesta de Miranda, a path that winds through stunning landscapes and is a haven for motorcyclists. Here, they greeted groups of riders from all over, riding bikes of various makes and models – BMWs, Ducatis, KTMs, Harleys, and more.

“The road doesn’t care about the brand or the engine size. It’s the spirit of the ride that unites us all,” Diego wrote about this experience.

Continuing their journey, they visited the Talampaya National Park and the Provincial Park of Ischigualasto, also known as the Valley of the Moon. Both parks offered contrasting yet equally impressive landscapes, with the former known for its towering red walls and natural statues, and the latter for its monochromatic, moon-like terrain.

Diego’s account of the day reflects his awe: “Nature’s canvas at Talampaya and Ischigualasto was a mesmerizing contrast – one painted in fiery reds, the other in lunar greys. Riding through these parks was like traversing different worlds.”

Their day ended in San Agustín del Valle Fértil, where they stayed in a cabin that turned out to be the owner’s home – a humorous twist to their accommodation plans, and a wonderful example of the unexpected generosity and hospitality they encountered on their journey.