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Join us for four days of spectacular riding and scenery through Oregon’s Cascade Mountain range. This tour has it all – breathtaking roads, scenic stops, and two nights at the Metolius River Resort.
Our tour will depart from Medford and take us into the heart of the Cascades, where we’ll ascend to the western rim drive of Crater Lake, enjoying the spectacular view from the Watchman Tower. We’ll then work our way north to the small towns of Oakridge and Westfir, our stop for the night.
Day two we’ll ride north on Hwy 19, the Auferdheide Dr, one of the most scenic drives in all of Oregon, only to then head east over the McKenzie Hwy 242, with views to match, and twisties to delight. After a stop at the Dee Wright Observatory we’ll head to our luxurious cabins at the hidden gem of Metolius River Resort. Two nights here give opportunity for a free day of ventures to The Blue Pool, or to Smith Rock, or perhaps some fly fishing, or even a day to luxuriate and rest at the resort.
Our last day we’ll start back by way of Bend, then taking the scenic Cascade Lakes Hwy that passes Mt. Bachelor and several beautiful lakes. After going over the pass, we’ll enjoy a magnificent stretch of highway and scenery, descending from Diamond Lake and down through Union Creek, into the Medford valley, where our tour concludes.
Medford, OR
July 12, 2026 8:30 AM, at 3550 National Dr. Medford
Our tour departs Medford Oregon and winds its way up sweeping curves to Crater Lake, where we’ll ride the west rim and stop at the Watchtower, where those that wish can hike the 15 minutes to the tower. For those that have never been, the views and the rim drive will be a spectacular treat! We’ll then continue north east to Hwy 97 before cutting west West on Hwy 58 to the towns of Oakridge and Westfir, where we’ll stay for the night. Make sure to ride the grandest covered bridge in Oregon, right there in Westfir.
From Westfir we’ll ride north on Hwy 19, know as Aufderheide Memorial Scenic Drive, a two-hour 54 mile bliss of nature that meanders between mountains and alongside the creeks. Some say it’s the best road in Oregon, but come see for yourself. There’s an option to stop and soak in the Terwilliger Hot Sprngs if you wish. We’ll then head east over Hwy 242, better known as the McKenzie Pass, a ride filled with beautiful hairpin turns up and through the forest, topping out at the Dee Wright Observatory. You’ll see more lava rock in any direction than you’ve ever seen, and the twisting ribbon of a road we’ll descend on the eastern side through lush forest will delight to no end. Our ride ends at the Metolius River Lodge, where we’ll be for two nights in luxury cabins right on the river.
When is the last time you had a day to do whatever you wanted? Set out for a short ride to explore Smith Rock, or The Blue Pool, or go fly fishing (bring your own rig, or reserve in advance and rent from Camp Sherman Store, and purchase your fishing license online before you leave home) in the Metolius River. The near-by town of Sisters has a old western flair of shops and resturants to explore, or just relax on your deck and read a good book. Hola restaurant is there on site, a Puruvian Mexican treat, and the camp store has food as well.
On our last day, we’ll head south through Bend, then take the scenic loop known as the Cascades Lakes Hwy. We’ll then turn west toward Diamond Lake, and descend down Hwy 62, a glorious stretch of road through towering evergreens, passing Union Creek and the Rogue River Gorge, as well as Lost Creek Lake, before entering Medford where we end the tour and say our goodbyes.
Note the special lodging for this specific trip, as our two-night stay at Matolius River Resort is a rare treat at an exclusively nice place and grounds that is more expensive than a typical hotel stay on bike tours. We think you’ll love it and want to come back with friends or family!
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So that your trip can be truly enjoyable, please read our Terms that answer many commonly asked questions about tour logistics.
