Itinerary
- Day 1
Bend
You'll meet up in Bend and start riding toward Mt. Bachelor, with volcanic Cascades stretching out ahead of you. The route takes you south through pine forests to Sunriver, then connects to bike paths leading to Lava Lands. Along the way, you'll stop to look into Newberry Crater, one of the region's cinder cones. After that, it's back to Sunriver for dinner and your first night at Sunriver Resort.
- Meals
- Dinner
Included Activities
- Bike ride from Bend toward Mt. Bachelor
- Ride through pine forests to Sunriver
- Bike on network of paths to Lava Lands
- View Newberry Crater
Landmarks/POIs Mt. Bachelor Newberry Crater Lava Lands 
- Day 2
Sunriver to Bend
This morning you'll cycle from Sunriver to Paulina Lakes, which sit on the edge of eastern Oregon's desert with that distinctive blue-green color. Paulina Falls is your next stop, where water drops 80 feet over a basalt cliff. From there, head into Bend to visit the High Desert Museum and learn about the region's natural history. Later you'll check out some of Oregon's craft brews on your own dime. You're staying two nights at McMenamin's Old St. Francis School, a converted schoolhouse that features a heated art-deco pool.
- Meals
- Dinner
Included Activities
- Bike ride from Sunriver to Paulina Lakes
- View Paulina Falls
- High Desert Museum exhibition
- Craft brewery sampling
Landmarks/POIs Paulina Lakes Paulina Falls High Desert Museum 
- Day 3
Bend
Start this morning with a half-day rafting trip on the Wild and Scenic Deschutes River alongside a local outfitter. The afternoon is yours to do what appeals to you, whether that's trying another adventure activity, walking around Bend, strolling the riverfront trail, grabbing time at a cafe, doing some birding, or checking out more brew pubs. Dinner is on your own tonight, and your guide will have plenty of restaurant recommendations for you.
- Meals
- Breakfast, Lunch
Included Activities
- Half-day rafting excursion on Wild and Scenic Deschutes River
Optional Activities
- Adventure activity of choice
- Explore town of Bend
- Stroll riverfront trail
- Café visit
- Birding
- Visit brew pubs
Landmarks/POIs Deschutes River - Day 4
Bend to Sisters
You'll ride the Crooked River Scenic Byway, a narrow and twisting basalt canyon route that takes you back to Oregon Trail history. The ride shows off snow-capped Cascade mountains, rim-rock canyons, high-desert pastureland, and tranquil rivers. At the end you'll reach Smith Rock, recognized as the birthplace of U.S. sport rock-climbing and one of the Seven Wonders of Oregon. After a short hike there, continue on to Sisters for the night at Five Pine Lodge.
- Meals
- Breakfast, Lunch, Dinner
Included Activities
- Bike ride on Crooked River Scenic Byway
- Short hike at Smith Rock
Landmarks/POIs Crooked River Scenic Byway Smith Rock 
- Day 5
Sisters
You're in for one of Central Oregon's most remarkable rides today on the east side of McKenzie Pass. Starting from Sisters, you'll cycle through open woodlands with a gentle climb into Willamette National Forest. At the summit, everything changes dramatically, the forest opens up and you're looking at an incredible lunar landscape with massive lava fields and snowy peaks in the distance. There's a short hike to Dee Wright Observatory, which was hand-built from lava rock by the Civilian Conservation Corps back in 1935. After that, you'll cruise back down to Sisters and finish with lunch at Three Creeks Brewery.
- Meals
- Breakfast, Lunch (Lunch at Three Creeks Brewery)
Included Activities
- Bike ride on east side of McKenzie Pass
- Hike to Dee Wright Observatory
- Lunch at Three Creeks Brewery
Landmarks/POIs McKenzie Pass Willamette National Forest Dee Wright Observatory
