Welcome to Bend, Oregon’s high desert cycling hub, where snow-capped peaks meet Ponderosa pine forests and the city’s bike-friendly culture sets the tone for adventure. After a bike fitting and orientation, set off on your first ride directly from town. Pedal beneath the shade of tall pines along the serene Skyliner Road, tracing the curves of sparkling creeks and alpine meadows. Those looking for a challenge can opt to climb towards Mount Bachelor, where the views open up to the Cascade Range, and volcanic ridgelines stretch into the distance. Post-ride, there’s no better place to relax than Bend. This lively town is home to dozens of microbreweries, food trucks, gear shops, and riverfront parks, perfect for unwinding after your introductory ride. __________________________________________________________________________________________________________________________ • Overnight - Bend, McMenamins Old St. Francis School or similar • Cycling: 22 miles / 35 km, Elevation gain/loss: ±1,000 ft / 305 m • OR 44 miles / 71 km, Elevation gain/loss: 3,100 ft / 945 m

Meals:  Nil

Wake up in the heart of Bend and ride one of the area’s most beloved routes, the Twin Bridges Loop. This scenic ride rolls across open high-desert terrain with sweeping views of the Cascade peaks. You'll pass sagebrush hills, quiet pastures, and the winding Deschutes River, all while enjoying the peaceful rural backroads. The ride includes a stop in the small community of Tumalo, a perfect place to pause for a coffee and take in the charm of the countryside. Back in Bend, the day is yours to relax, explore a riverside trail, or explore the city’s thriving food and craft beer scene. __________________________________________________________________________________________________________________________ • Overnight: Bend, McMenamins Old St. Francis School or similar • Cycling: 36 miles / 58 km, Elevation gain/loss: 1,600 ft / 490 m

Meals:  B

After a brief transfer to Sisters, ride one of Oregon’s most iconic stretches of road. The route up McKenzie Pass takes you on a steady climb through shady Douglas fir forests before opening into an otherworldly landscape of ancient lava flows. At the summit, you'll reach the stone-built Dee Wright Observatory, with panoramic views of the Cascade peaks like the Three Sisters, Mount Washington, and Mount Jefferson. The descent offers enjoyable and satisfying stretches back to Sisters, a small town with Western charm, local galleries, and mountain appeal. It’s a big ride and a rewarding one, with unforgettable terrain at every turn. McKenzie Pass typically opens mid-June, depending on snowmelt and the road’s reopening. The ride up Indian Ford Road is a great alternative if you plan your trip before McKenzie Pass reopens.  __________________________________________________________________________________________________________________________ • Overnight: Sisters, FivePine Lodge or similar • Cycling: 30 miles / 48 km, Elevation gain/loss: 2,260 ft / 690 m • Van Transfer: 30 minutes

Meals:  B

Leave the forested slopes behind and ride eastwards into Oregon’s high desert, where sagebrush plains, working ranches, and wide-open skies define the landscape. Today’s route leads to the dramatic cliffs of Smith Rock State Park, a world-renowned climbing destination and one of Oregon’s most spectacular natural landmarks. Here, jagged spires of volcanic tuff and columnar basalt tower above the meandering Crooked River, creating a stunning contrast of golden rock and verdant valley. Take time to walk a short trail into the canyon, watch climbers scale the sheer rock faces, or simply enjoy the surreal beauty of this desert oasis. A casual lunch in nearby Terrebonne makes for an ideal mid-afternoon break before continuing to your hotel in Redmond. __________________________________________________________________________________________________________________________ • Overnight: Redmond, SCP Hotel or similar • Cycling: 46 miles / 74 km, Elevation gain/loss: 1,300 ft / 400 m

Meals:  B

Your final ride brings you full circle, looping back to Bend through a patchwork of farmlands and rolling hills, with views of the Cascade peaks lining the horizon. The terrain is gentle and open, perfect for reflecting on the week’s journey through Oregon’s diverse landscapes, from alpine forests to desert canyons. Back in Bend, celebrate your week’s journey with a well-earned lunch or a final pint at one of the city’s renowned breweries. After returning your bike and settling back into the familiar comfort of McMenamins, unwind with a riverside stroll or a soak in the hotel’s iconic soaking pool, an idyllic sendoff from this beloved Pacific Northwest gem. __________________________________________________________________________________________________________________________ • Overnight: Bend, McMenamins Old St. Francis School • Cycling: 25 miles / 40 km, Elevation gain/loss: ±1,300 ft / 400 m

Meals:  B

After a leisurely morning and perhaps a visit to one of the many great local coffee shops, head out to your next adventure. __________________________________________________________________________________________________________________________

Meals:  Nil