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.
 

Hiking Misery Ridge

Twenty-seven miles north of Bend, lies one of the “Seven Wonders of Oregon”: Smith Rock State Park. After going to such a grand national park as Crater Lake, our expectations weren’t too high for this place, but it completely dazzled us! The Crooked River cuts through sheer red mountains of tuff and basalt, and world-class climbers scale its cliffs from all angles. Some even consider Smith Rock the birthplace of modern American sport climbing and there are more than a thousand bolted routes on offer. If you prefer to keep your feet on the ground, take the 3.8-mile Misery Ridge Loop Trail for a challenging hike with immensely rewarding views of the dramatic park and the Cascade Range.
 

Glamping the High Desert

Panacea at the CanyonAll these mountain adventures warranted a bit of R&R (any excuse for a bit of pampering) so we checked into Panacea at the Canyon. An off-the-grid glamping retreat set on the cliffs of the Crooked River, this place was built with nine years of hard work and passion by a husband-wife team. The co-owner Darren, artist and hot-air balloonist by trade, greeted us and his wife showed us the way to the teepee spa for our chakra-balancing treatment. We were sent into a state of bliss that carried through our two-night stay, with walks in the meditation labyrinth and sun salutations on the cliffside yoga deck. Whether you use Panacea as your base camp for adventures in central Oregon or as a retreat away from it all, this place is worth a visit. We loved it so much we included it in our upcoming glamping book, Comfortably Wild!
 
Oregon beer tastingTop off your Oregon road trip with a scenic drive around Mount Hood, before finishing in Portland for a craft beer and cheers to the road less traveled!

15 thoughts on “The Ultimate Oregon Road Trip: The Cascades

  • February 2, 2018 at 11:33 am
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    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!

    Reply
  • June 2, 2019 at 8:06 am
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    What caught my attention was the deepest lake in the United States at 1,949 feet. The deep blue color surrounded by those pristine white mountains would make me stare on and on. The artsy stop…yes please.

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    • June 2, 2019 at 8:31 pm
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      Crater Lake is incredible! If you like to snowshoe, come in May for few crowds and pleasant temps. Ashland is a ton of fun too..you’ve gotta catch a Shakespeare performance!

      Reply
  • June 3, 2019 at 4:00 am
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    Ah it would be an amazing experience to walk with the pack of goats, plus the fire-heated hot tub doesn’t sound too bad! I do need to learn to drive, still on my list (keeps getting taken over by holidays)

    Reply
  • June 3, 2019 at 11:12 am
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    I still haven’t made it to the US. But I know when I will go there I want to take a road trip. I should save this post. I would like to go to Highway 62 and visit the Volcanic Legacy Scenic Byway. It sounds so appealing

    Reply
  • June 3, 2019 at 9:23 pm
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    What a fun road trip! The Willow-Witt Ranch looks like something out of Heidi. I visited Bend a few years ago and managed to finish the Ale Trail while still standing. 🙂

    Reply
    • July 8, 2019 at 4:36 pm
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      Willow-Witt is a special place…it’s featured in our next book “Comfortably Wild: The Best Glamping Destinations in North America” Well done on the Ale Trail btw 🙂

      Reply
  • June 4, 2019 at 6:28 am
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    This looks like a fantastic road trip. The stunning views of nature and getting into the towns to try out the local fare is a great way to see the country. I’ve heard great things about Bend, now it’s time to go! Plus glamping and beer tasting? I can’t wait to see this part of the country! Thanks for sharing!

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    • July 8, 2019 at 4:37 pm
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      Glamping + Beer Tasting + Hikes…the Cascades Range is heaven. Glad you enjoyed the post!

      Reply
  • June 7, 2019 at 5:24 am
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    What a gorgeous set of landscapes. Loved the Crater lake the most followed by Misery Ridge. Curious though why it is called Misery Ridge. Is it akin to Suicide point found in most places?

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    • July 8, 2019 at 4:40 pm
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      The Cascade Range is nonstop beauty! The name “Misery Ridge” is definitely a bit offputting but it’s worth the steep climb and the views are so fantastic it wasn’t miserable AT ALL.

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  • June 9, 2019 at 4:34 am
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    Hiking at the Misery Ridge seems very interesting! I would want to take a photo just like that, too! But I believe it’s not a child-friendly hike so I would rather choose to take the kids at BEND, seems family friendly and let them experience the camp in the wild when we go to Oregon next year! Thanks for the info! Love your site!

    Reply
    • July 8, 2019 at 4:33 pm
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      Thanks so much! How old are you’re kids? We had friends who just did the Misery Ridge hike with 10 kids, some as young as six years old. They had a blast! That said, Bend is fantastic too, especially with all their events on the river. Happy travels!

      Reply
  • July 19, 2019 at 7:14 pm
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    This all looks incredible but Willow-Witt Ranch sounds like a must-visit for the experience! Did you book ahead or upon arrival?

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    • August 31, 2019 at 10:12 pm
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      Thanks, Lindsey! Willow-Witt is awesome. We booked in advance; they are a small operation with a lot of heart! If you like them, you’ll also love the other farmstays featured in the Cultivate Chapter of our next book Comfortably Wild

      Reply

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