Distance: 37 miles | Terrain: Intermediate | FivePine Lodge
The trip begins with a welcome meeting at 8:30 a.m. in Bend, an easy shuttle ride from the Redmond Airport (RDM). Bring your luggage and be ride-ready. After brief introductions, you hop into the van and shuttle to Smith Rock State Park, where you have an Orientation Meeting, get fitted on your bike, and begin your Central Oregon adventure. Explore Smith Rock a bit on foot or two wheels. Watch rock climbers from all over the world as they cling to Smith Rock’s striking walls and colorful volcanic formations. On today’s Scenic Bikeway, you follow the Deschutes River, passing through forests, agricultural areas, and high desert country. You end your ride at the FivePine Lodge in Sisters. The community is named after the Three Sisters peaks — Faith, Hope, and Charity. More than 10,000 ft in elevation, the peaks, are part of the Cascade volcanic arc and are the third-, fourth- and fifth-highest in the state. Dinner is at a local restaurant.

Distance: 27 or 39 miles | Terrain: Intermediate to Advanced | FivePine Lodge
Today’s postcard showcases images of out-of-this-world moonscapes created by a 2,000 year-old lava flow. The McKenzie Pass Scenic Bikeway follows an 1870s wagon toll road. For those of you wanting the challenge of a 2,400 ft climb up McKenzie Pass, you’ll relish the pine-filled air as you pedal up the mountain. For those of you wanting a more relaxing ride, shuttle to the top of the pass and enjoy the seemingly never-ending descent. At the 5,325 ft summit, the Dee Wright Observatory offers fantastic 360-degree views and highlights the nearby prominent peaks of the Cascade Mountains. On your 20-mile-long descent, stop at the Proxy Falls Trailhead and enjoy a leisurely 1.6 mile-long hike to two of the most photographed waterfalls in all of Oregon. At the far end of the Bikeway, soak in the Belknap Hot Springs before boarding the shuttle back to Sisters. You are on your own for dinner tonight, so there is plenty of time to schedule a relaxing session at the Shibui Spa.

Distance: 23, 32 or 38 miles | Terrain: Easier or Intermediate | Pine Ridge Inn
Today’s postcard views are inspired by the Twin Bridges Scenic Bikeway. You begin and end your cycling in Bend. At the beginning of the ride, stop at the Bend Whitewater Park and watch surfers ride the wave in the Deschutes River. Further along the route, pass through high deserts, pastures of hay, hobby farms, and wildlife areas. All the while, you’ll have spectacular views of the snow-capped Cascade Mountains. Enjoy a true Pacific Northwest-style lunch from one of the many food carts in the charming town of Tumalo. Dinner is on your own tonight. If you wish, spend the evening hours at one of the famous McMenamin properties — Old St. Francis is a rehabilitated parochial school turned into a funky lodge, brewpub, soaking pool, and more!

Distance: 18 or 37 miles | Terrain: Easier or Intermediate | Crater Lake Lodge
Today your postcard views are chockfull of lakes and mountains along the Cascade Lakes Scenic Byway. The highway, which was originally paved with red volcanic cinders in the 1950s, was once called Century Drive because it was a 100-mile round trip between Bend and Elk Lake. If you wish, you can begin today’s ride right from the Pine Ridge Inn and pedal up to the volcanic Mt. Bachelor (no worries, it’s been more than 8,000 years since the volcano last erupted). Alternatively, ride in the van to the top of Mt. Bachelor and enjoy the lovely descent. Along the route, stop for views of Sparks, Devils, Elk, and Lava Lakes. We’ll enjoy a group lunch at Lava Lakes, where you can catch an hour-long peaceful paddle before hopping in the shuttle to Crater Lake National Park. You spend the next two nights at the historic Crater Lake Lodge, which overlooks the lake’s pristine blue waters nearly 1,000 ft below. Dinner tonight is at the Crater Lake Lodge Dining Room.

Distance: 16, 24, or 35 miles | Terrain: Intermediate to Advanced | Crater Lake Lodge
The backdrop for today’s postcard is the drool-worthy Crater Lake — one of the deepest clearest, and bluest lakes in the world. Stop at the many pullouts to admire its pristine waters and the enchanting Wizard Island, a 763-foot cinder cone in the middle of the lake. You might even need to pinch yourself and ask: Am I in a dream? From every angle, Crater Lake is surrounded by volcanic peaks, verdant forests, and fertile valleys. It’s ABSOLUTE BLISS! As the ride around the lake’s rim is challenging, there are plenty of shuttle options to customize the ride to your desired perfection. Dinner tonight is at the Crater Lake Lodge Dining Room.

Optional Hike
Wake up this morning and savor the breathtaking views with a cup of coffee on the back deck of the lodge. Or perhaps rise a bit earlier and hike the nearby Garfield Peak or Discovery Point Trails. Either way, you relish in the postcard memories you’ve made in Central Oregon. Mid-morning we provide a shuttle back to our starting point in Bend, where we say our goodbyes.