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 scope out Willow-Witt Ranch for our glamping book. 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! For more fabulous farmstays, check out the “Cultivate” chapter of Comfortably Wild.
Crater Lake National Park
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
All 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!
Top 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!
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!
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.
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!
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)
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
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. 🙂
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 🙂
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!
Glamping + Beer Tasting + Hikes…the Cascades Range is heaven. Glad you enjoyed the post!
First thing that comes to my mind is , are the days always so sunny & beautiful? The volcanic crater lake is spectacular. I am sure the volcano is dead now. All in all it looks like you guys had a wonderful road trip.
hahahaah….great question Vasu. The days aren’t always THAT sunny and beautiful…sometimes they are rainy and beautiful…sometimes they are sunny and boring with work and zoom calls….but the fact that we can make our own choices and don’t have a boss telling us when to dance, that makes it ALL worth it!
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?
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.
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!
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!
This all looks incredible but Willow-Witt Ranch sounds like a must-visit for the experience! Did you book ahead or upon arrival?
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
WOW! I love how you describe the places, and your photos are gorgeous. You’ve convinced me to take a trip to Oregon and enjoy those landscapes. thank you for sharing this experience!
OMG, thank you so much for the kind words Alex. I will be sure to tell Anne how much you appreciate the descriptions….she is our master story teller. You totally need to make it to Oregon, the landscapes there are ridiculous!
Oregon is one of the coolest states in the USA, especially for nature and beer lovers!
You got that right brother. We absolutely adore Oregon. Oh and you can add in Wine, Cider, Ocean, Mountain, and RV lovers. Oregon has something for everyone.