Notes From The Trail: Oregon Trail Gravel Day 1 — A Warm Welcome to the Wild West
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Daily dispatches from rider, racer, writer, photographer Caroline Dezendorf
On Wednesday morning, under cloudless blue skies and with the scent of pine in the air, 300 riders gathered at the start line of the Oregon Trail Gravel Grinder. Known for its five-day point-to-point route through Oregon’s rugged Cascade Mountains, the event isn’t just a race—it’s a bucket-list adventure race. Riders come to test their limits, while making new friends, and soaking in the scenery that makes this event one of a kind.
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As the sun moved high in the summer sky above the starting arch at Seventh Mountain Resort, the excitement was palpable. Nervous laughter filled the air as last-minute tire pressure checks were made and jersey pockets were stuffed with gels. Around the start line, hugs and high-fives were exchanged as riders reunited with old friends and made new ones. For many, this was more than a race start—it was a reunion and a celebration of the gravel community.
Toeing the line were several seasoned pros, including Sofia Gomez Villafañe, Sarah Sturm, and Rob Britton, all of whom were returning for another go at the Oregon Trail. But the real heart of the event lies in the diversity of its participants: hundreds of amateur and adventure-focused riders from across the country and around the world, each with their own goals, stories, and reasons for showing up.
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“We saw that [Oregon Trail] is an all-inclusive [experience], like going to Cancun, except to ride your bike,” laughed Desiree Taylor, who traveled from the Oklahoma City with her husband, Gabriel, to take part. “People at work were like, ‘So you’re going to ride your bike?’ And I’m like, yeah. ‘You’re not going to sit on the beach?’ No—we’re going to ride bikes.”
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Desiree and Gabriel planned their cross-country vacation around riding the Oregon Trail. They’re here for the challenge, but mainly the experience. For them, riding across remote parts of Oregon, sharing meals, and sleeping under the stars is far more enticing than a beach resort.
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Day 1 of the Oregon Trail, which took riders from Bend to the small town of Gilchrist, is often considered the most tame of the five stages—but it’s no walk in the park. The Pioneers tackled an 80-mile route with about 4,500 feet of elevation gain, while the Settlers rode a 65-mile route with nearly 3,000 feet of climbing.
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Despite the sandy and sometimes loose volcanic rock typical of the eastern Cascades, riders were rewarded with fast-moving roads and expansive views. Much of the course was shaded by towering pine forests, but as the day progressed and riders neared Gilchrist, the landscape began to open up. If they took a moment to look up from their handlebars, they were treated to iconic views of Mt. Bachelor and the Three Sisters peaks rising in the distance.
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“Today was really good,” said Catie George, a first-time Oregon Trail participant who made the trip from Virginia with her boyfriend, Cameron Jones. Cameron had just taken the win in the Pro Men’s field on Stage 1, while Catie was tackling her very first gravel race. “Meeting all the other racers was super cool. And I’m looking forward to improving over the next few days as I get more comfortable on the bike and on the terrain.”
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For Catie and many other riders, Oregon Trail is a personal challenge—a chance to push themselves in unfamiliar conditions. The dry, sandy, high desert terrain of Central Oregon is a far cry from the smooth gravel in other parts of the country. But that’s part of the magic. Every day brings a new challenge, a new landscape, and a new story.
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By mid-afternoon, riders rolled into the Gilchrist campsite, greeted by cheers, cold drinks, and the smell of dinner cooking. Some stretched out in the grass while others sat lazily in chairs, swapping stories from the day. It was only the beginning of the week, but bonds between racers were forming—over dusty roads, shared snacks, and the knowledge that tomorrow would bring more of the same.
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“Today was a good warm-up for what’s to come,” said race director Chad Sperry with a grin. “Tomorrow’s stage is probably the best one I’ve ever designed. I think it’s going to be an incredibly exciting day.”
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If Day 1 was the prologue, Day 2 promises to be the heart of the story. For now, riders will rest under a canopy of stars, legs tired but spirits high, ready for whatever the Oregon Trail throws at them next.