This post is written for my friend Lila. Enjoy!

My amazing life partner, Kendel and I, just wrapped up an epic Oregon road trip loop….about 28 hours of drive time, endless laughs, and more waterfalls, breweries, and small motels than I can count. We flew into Portland from Minneapolis and hit the ground running.

Portland Kickoff

We stayed at the Kex Hotel in the heart of East Portland….super cool vibe.

First stop? Accidentally stumbling onto the legendary Burnside Skate Park. Then, by pure luck, we wandered into Powell’s City of Books….the largest independent bookstore in the world. Total gem!

Dinner that night was at Noble Rot, where I tried duck for the first time (amazing) while staring out at Portland’s skyline. Highly recommend!

The next morning started with Pine State Biscuits (killer biscuits and gravy, plus a chicken sandwich that was unreal) and a yoga class at Sellwood Yoga, tucked away in green space that felt like a secret garden.

Waterfall Country

From there we hit Multnomah Falls for a 5-mile hike. Kendel complained the whole way (JK….to be fair, it was a lot of elevation), but by the end, it became one of her favorite parts of the trip. We saw 6 or 7 waterfalls, all jaw-dropping.

That night we stayed at the Westcliff Lodge, right on the river with pretty gardens. Solid spot.

Painted Hills & Madras

Next up was the Painted Cove Trail, a short hike around lava dome–looking rock formations. Small but worth it. We overnighted in Madras at the Bunkhouse, which bills itself as “where Yellowstone meets the high plains.” The town? Meh. But the margaritas at Rio Distinctive hit the spot.

Smith Rock & Sisters

The following day was Smith Rock State Park….a rock climber’s paradise. Short hike, incredible views. Then on to Sisters, where we decided to try day drinking but Kendel shopped while I tested the limits of ZBiotics, the hangover preventer (spoiler: I still got wrecked). Hahahahahaha!

We stayed two nights at Five Pine Lodge, which was hands-down one of our favorite stays. Beautiful cabins, a soaking tub, fireplace, even a movie theater on the property.

Hot Springs & Crater Lake

From there we drove to Umpqua Hot Springs….natural pools overlooking the forest. Unreal. On the way out, we hiked Toketee Falls (Kendel’s favorite waterfall of the whole trip).

That night we stayed at Crater Lake Country Suites which is kind of like a AirBNB but really in the middle of nowhere. Very little amenities but the spot was cute and quaint. Dinner was at a random Mexican restaurant 15 miles away called the El Rodeo and no joke, best burritos we’ve ever had.

The next day was Crater Lake National Park. We drove the 33-mile Rim Trail, hiked down to the water (yes, I cliff-jumped as you can see in the video up above), and watched the sunset at Cloud Cap. Magical.

Brookings & the Redwoods

We overnighted in some questionable motels (Edgewater Inn, looking at you) before making it to Brookings. On the way, we dipped into Redwood National Forest just south of the border. Mind-blowing doesn’t even cover it.

In Brookings, we caught live music at Oxen Free where they covered “Wooly Bully”….instant flashback to my dad. We also played a co-op card game, Sail. Kendel was more worried about wildfires than winning, but it was still fun.

Up the Coast

We cruised north on Highway 101, soaking in endless coastal lookouts. Stayed in Reedsport at the Anchor Bay Inn (the dumpiest stay of the trip). The bed sagged in the middle big time so although it was a king, it felt like a single bed. Hahahahahahahaha

For Kendel’s birthday, it rained all day, so we saw Eleanor the Great at a tiny local theater (10/10 movie, tears everywhere). GO SEE THAT MOVIE! Then we checked into Overleaf Lodge & Spa, perched right on the ocean. Massages, balcony views, takeout dinner….pure magic.

My Birthday & Cannon Beach

The next day….my birthday….we rolled into Cannon Beach. Lunch at Pelican Brewery (shoutout to our awesome server, Asher), beers with a view, then hit the Tillamook creamery and then we finally checked into the Hallmark Inn & Resort. Our balcony looked right out at Haystack Rock….straight out of The Goonies.

We wrapped it up with dinner at the Wayfarer Restaurant. I ordered the seafood bake, expecting a cozy casserole situation, but what landed in front of me was basically a seafood stew. Don’t get me wrong…..it was delicious. But by the time I was done, I was basically covered head to toe in butter and sauce. Totally worth it, just… a lot of work!

Oregon delivered! From waterfalls to redwoods to coastlines to burritos that changed our lives, it was a trip full of laughs, surprises, and some seriously sweet moments.

This piece was edited using ChatGPT from a transcription of my personal audio recording

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