Oregon Road Trip
Everyone knows about iconic U.S. road trips like the Pacific Coast Highway or Route 66, but hugging the curves of the Cascade Range? This has been one of our favorite legs on our 8,000 mile journey across the States. Within the Pacific Ring of Fire and running from Northern California to southern British Columbia, this mountain range is stunning across the board. Though to tackle it without crampons or a month of vacation time, we’d vote for the Oregon route between Ashland and Terrebonne. Spunky towns, glaciated mountains, high desert, craft beer country, and more adventure than an adrenaline junkie knows what to do with, our Oregon Road Trip through this slice of the Cascade Range has it all.


Oregon Road Trip: The Route

Distance: ~300 miles
Timing: 2 nights Ashland, 1 night Crater Lake National Park, 2 nights in Bend, and 1-2 nights Portland.


Get Artsy in Ashland

We pulled into Ashland and liked it instantly. A university town with a world renowned theater company, it exudes energy, creativity, and small-town charm. From February-November, catch a play or music performance at the Oregon Shakespeare Festival, and Tuesday and Saturday shop the Rogue Valley Grower’s & Crafter’s Market. The pride for all things local is infectious.


Farm Stay at Willow-Witt Ranch

Just 12 miles from Ashland, nestled in a mountain valley covered in wildflowers, a historic and working organic farm has opened its doors to curious travelers and foodies. Even though Ashland is a destination in its own right, we actually came to the region just to experience Willow-Witt Ranch. More than a farm, it’s a project to conserve this unique ecosystem and get people of all ages in touch with the food we eat.

We slept in cozy canvas cottages and woke up with the sun to harvest spinach and arugula, gather eggs from the coop, and learn the ropes of goat milking from the lovely owners, Lanita & Suzanne. We spent our afternoons trekking the 445-acre property with their friendly pack goats, cooking up our hand-harvested delights, and capping off the day in the fire-heated hot tub under a blanket of stars. Spend a night or come for their day-tours…you won’t forget it!


Crater Lake National Park

Oregon Road Trip
Make your way east to Highway 62 and hop on the Volcanic Legacy Scenic Byway, with a special pit stop at the raging Rogue River Gorge and Beckie’s Cafe for an amazing slice of pie. An eruption over 7,000 years ago created a pumice desert and a profound caldera, now Crater Lake National Park.

Cruise along the 33-mile Rim Drive, breaking for countless photo ops of the deepest lake in the United States at 1,949 feet. The full loop and many of the trails are only open in mid-summer and early fall, so drive or hike as far as you can, and if all else fails there are snowshoe rentals and cocktails at the historic, Crater Lake Lodge.


Bend: Beer, Music, and an Enviable Place to Live

Whether you take the straight-forward highway 97 or detour from Sunriver onto the Cascades Lakes Scenic Byway, you won’t be disappointed arriving to Bend. As sporty and entrepreneurial people, we’ve always had a little fantasy about moving here. It seems everyone is a skier, kayaker, brewmaster, artisan, or webmaster. We dove right into Bend culture with a music festival on the river (check the summer events calendar, it’s packed with fun!) and a few stops on the 16-brewery Bend Ale Trail.

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One thought on “The Ultimate Oregon Road Trip: The Cascades

  • February 2, 2018 at 11:33 am

    We lived in Eugene, Oregon for 7 years and can’t agree more that the Cascades are absolutely stunning. Despite spending every spare weekend kayaking, hiking, and camping, we left with a bucket list of places we didn’t get to explore. All the more reason to go back!


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