Notes From The Trail: Daily Dispatch — Stage 2 — Into the Heart of the Cascade

Daily dispatches from rider, racer, writer, photographer Caroline Dezendorf

Daily Dispatch — Stage 2 — Into the Heart of the Cascades

The sun rises early in the eastern Oregon sky, casting a golden hue across the tents dotting the Little Deschutes River at the historic Gilchrist Waterfront Resort. As the new day began to dawn, the quiet rustling of sleeping bags and murmured conversation signaled the start of Stage 2 on the Oregon Trail. Campers slowly emerged from their tents, blinking into the morning light, stretching sore muscles and shaking off the chill of a high desert night.

The smell of freshly brewed coffee from LOAM Coffee Roasters drifted through the air, cutting through the quiet with a comforting familiarity. Breakfast, prepared by the hardworking crew at Spin Catering, offered a hearty spread of eggs, sausage, hash browns, bagels with cream cheese, and a tempting selection of pastries. It was the kind of breakfast designed for a long day in the saddle—comforting, caloric, and just indulgent enough to make everyone feel taken care of.

As caffeine made its way into everyone’s bloodstreams and calories began to settle, the energy in camp shifted. Conversations turned toward gear choices, tire pressure, and fueling strategies for the day ahead. Excitement buzzed through the air—anxious but eager—as riders prepared for the grand departure from the high desert toward the deeper, denser woods of the western Cascades. Today’s destination: Oakridge.

From Gilchrist, both Pioneers and Settlers rolled out together under clear skies and cool morning temperatures. The day began on quiet mountain pavement, where groups settled into rhythms beneath the towering pines. But this wouldn’t be a day to settle in for long. Stage 2 would be a journey of contrasts—sun and shadow, sand and loam, hard climbs and exhilarating descents.

Early on, the terrain revealed its dual personality. The course wound through a mosaic of volcanic rock, soft sand, and pine-lined doubletrack. The first quarter of the stage challenged riders with technical sections of loose, deep sand. Each corner brought a new variable—dust-covered rocks, shifting lines, occasional patches of firm dirt that made riders momentarily feel invincible—before plunging them back into the sandbox.

As the route progressed and the elevation increased, so too did the vegetation. Pines gave way to dense hemlocks and lush undergrowth filled with ferns, and the dry heat of the high desert began to lift. Riders were soon immersed in the cool green of the Cascade Range’s western slopes. The gravel firmed up, the climbing became sustained and punchy, and the oxygen thinned as the trail approached the Pacific Crest, hovering near 6,000 feet in elevation.

And then came the water.

Massive murky puddles from recent snowmelt turned parts of the route into full-on water crossings. Some riders dismounted and tiptoed around the edges, others barreled straight through, emerging with soaking shoes and grins stretched across their mud-speckled faces. It was messy, unpredictable, and deeply memorable.

After cresting the pass, riders were rewarded with a long, flowing descent into the lush forests surrounding Oakridge. The descent was one of those rare gravel moments where time seemed to disappear—fast, technical, and pure fun.

“That was awesome!” “The descent was so fun!” “I loved that stage!”

As the day wound down and riders began to trickle into the Oakridge camp, the post-ride vibes were as high as the climbs that had brought them there. Legs were tired and bikes were caked in mud, but spirits were alive. The loudest conversations revolved around the route—its beauty, its brutality, and the perfect pacing that made it feel like an earned adventure.

Many made a beeline for the icy waters of the Middle Fork of the Willamette River, which ran cold and fast just beyond the edge of camp. Submerging sore legs and dusty faces in the water quickly became a communal ritual—part recovery, part celebration.

Sitting in the river, sipping a cold beer, surrounded by friends and fellow adventurers, laughter echoing across the water—it was hard to imagine a better way to end a day on the Oregon Trail.