The Essential Central Oregon Bike Tour

Welcome to the vibrant town of Bend! We're about to kick off our adventure with an optional spin around downtown and along the scenic river trail. Next, we'll cycle to the renowned Deschutes Brewery, a pillar of Bend's thriving beer culture since the late '80s. There, we'll get a sneak peek into their brewing magic, followed by a taste of their renowned brews. Our journey carries on at Deschutes Public House, where a dinner inspired by the art of brewing is set up for us. We wrap up the day at the quirky McMenamins Old St. Francis School. This revamped 1936 schoolhouse-turned-hotel is a trove of charm, with art commemorating its history and a relaxing soaking pool. We're all set to dive into local culture, tastes, and tales together - the perfect launch pad for our thrilling adventure ahead.

Our first official day of biking gets underway on the captivating Crooked River Scenic Bikeway. We're riding through the timeless beauty of narrow, basalt canyons, reminiscent of the old Oregon Trail days. Our backdrop? The grandeur of the Cascade Mountains, peaceful rivers, and expansive high-desert pastureland on our journey to Smith Rock.

Our mid-point sees us dropping by Prineville for a bite at the legendary Tastee Treet. A go-to spot for delicious burgers, homemade fries, and retro shakes, it's been winning over locals for more than half a century.

Refueled, we press on to Smith Rock, celebrated as the birthplace of U.S. sport rock-climbing and one of Oregon's Seven Wonders. There's an optional hike to the top on offer - brace for awe-inspiring views and a light picnic at the summit. Be on the lookout for golden eagles and river otters!

We'll cap off the day with dinner at Terrebonne Depot before heading to Smith Rock Resort. Our night's rest is in unique yurt-style rooms with grand views of the Crooked River canyons.

Day three sees us riding the Sisters to Smith Rock Scenic Bikeway in reverse. Our ride will whisk us past historic landmarks, follow the curves of the Deschutes River, and offer spectacular vistas of the Cascade Mountains. The route unfolds through tranquil forests, fertile valleys, and charming riverside paths.

Around the mid-point of our journey, we'll pause for a well-deserved lunch break at Faith Hope & Charity Vineyards. Surrounded by the captivating Central Oregon landscape, we'll savor a delicious meal and partake in a spot of wine tasting.

Once our cycling adventure concludes, you'll have free rein to explore downtown Sisters. This 1880's western-themed town is a haven of unique boutiques, vibrant galleries, and a rich local culture waiting to be discovered.

At the end of the day, we'll retreat to the comfort and luxury of the FivePine Lodge & Spa. Combining the warmth of a bed and breakfast, the privacy of secluded cabins, and all the amenities of a high-end resort, it's the perfect way to round off an exhilarating day.

Day four kicks off at Sisters Coffee Company, a local treasure that has been brewing up a storm since 1989. We'll warm up with their expertly crafted coffee and a wholesome breakfast to fuel the day ahead.

Next up is the ride along McKenzie Pass Scenic Bikeway, an iconic route showcasing Oregon's stunning geological beauty and breathtaking landscapes. The climb to the top is an exhilarating challenge, but reaching the summit to the Dee Wright Observatory, with sweeping views of mountains, buttes, and the path we've traversed, is the perfect reward.

We wrap up the day, and our trip, at the historic McKenzie General Store. Established in 1932, it's a spot that seamlessly blends history, local allure, and delightful food. Over a celebratory lunch, we'll look back on our adventure, cherishing the memories of our extraordinary four-day journey.