Oregon Road Trip Highlights

By Kate Riley October 8, 2021

I spent the first week of August exploring the state of Oregon, a place I had never been to before even though it’s my neighbor to the north. On my road trip, I stopped in Ashland, Portland, Hood River, and then drove the entire Oregon coast home all the way back to California.  It was a lot of driving but I wanted to visit my northern neighbor by car to see the mountains, rivers, and explore the towns.

I had to make my way through several northern counties in California before crossing the border. The golden plains turned to hills and then mountains covered in forests as I made my way toward the Pacific Northwest. It was almost dusk as I crossed the border into Oregon where I stopped on the side of the highway to photograph the “Welcome to Oregon” sign as semis whizzed past me at high speeds almost blowing me over.

At sunset I arrived in Ashland, Oregon and I had just enough time to make a last seating for dinner downtown. I dined under globe lights in an outdoor cafe and while I ate I struck up a conversation with a local theater manager. She offered me a quick walking tour of the town after dinner, pointing out various sights I should see during daylight. Friendly locals always have the best tips and remind me of the kindness of strangers.

The next morning I set out on foot to explore the town in daylight and snapped a few photos with my phone. Ashland is known for its theater productions but I will remember it for its small town charm. Highlights: the interior of the historical Ashland Springs Hotel which will transport you to another time, and the very cute shops and restaurants next to Lithia Park.

After soaking up the parks, cafes, and shops I headed north to Portland. I didn’t get to spend anytime in Bend, which I’ve heard is really wonderful and in hindsight I wished I’d budgeted an extra day to see it.

Arriving in Portland my immediate impression was the opposite of Ashland. It was big, crowded, and confusing to navigate. I checked into the Hoxton hotel and headed to the rooftop bar to relax with tacos and sunset views.


I loved the interior of this hotel, its decorated with a chic mid century vibe (see more pictures here) and it was a cozy place to relax and have morning coffee.


I explored Portland on foot for two days. They take pride in their local motto “Keep Portland Weird” and I had mixed feelings about Portland downtown, but I found some spots that were cool like Pioneer Square and the Pearl District.

In Portland I discovered (and I had been warned) that the city struggles with a serious homeless population. The downtown areas are covered in tents and there were a lot of transients walking around. It’s tragic and those of us who know San Francisco are acutely aware we have the same problem. I don’t know the solution but I do know it impacts the vibe of a city.

The highlights of Portland for me were popular Powells Books, the Saturday Portland market, and my outdoor lunch at Luc Lac kitchen. My most favorite stop was my hike through Washington Park to the zen Japanese garden, it was so beautiful and worth the long walk to that side of town and uphill hike through the park.


I left Portland and headed east to Hood River, a town I’d been wanting to see since reading about it. The drive east is beautiful, winding through the Pacific Northwest along the Columbia River, it’s hard to keep your eyes on the road with such natural beauty all around!

Hood River looked like a place where they’d film a Netflix series. You know they type: a few charming downtown streets filled with shops, cafes, and breweries, surrounded by craftsman style homes, where life moves slowly and it feels like everyone meets for coffee every morning and knows everyone in town.

I rented a private room at the best Airbnb that was decorated with such cute and quirky furnishings and decor.

I had two amazing experiences in Hood River, the first was whitewater rafting with ZooRaft. So much fun! As a solo passenger I was partnered with a really cute family and spent a few hours riding rapids and drifting down river with them. It was one of the most pleasant travel experiences I’ve ever had, being on the water riding through a canyon surrounded by beautiful forests.

Hood River is a place where there are a lot of outdoor adventures: windsurfing, kayaking, and hiking, no wonder it’s such a happy place to be!

Another highlight was the Gorge White House, a stop recommended to my by my cousin. This farm had orchards and flowers and delicious hard cider, I highly recommend this place if you’re ever in Hood River!

I left Hood River and followed the Columbia River to the coast. What a beautiful drive!

I took two days to drive the Oregon coast home, it was a long but another extremely scenic drive. I started in Astoria where the Columbia River meets the Pacific Ocean and turned south down Highway 101. Astoria has a really cool maritime museum and a really cute downtown where I stopped for an early dinner at a great brewpub.

I stayed for a few hours then headed down a gently winding highway to stop in Seaside for dinner and to sleep for the night.

I could tell why Seaside was a vacation destination. It had a very cute downtown and beautiful beaches! I stayed at the chic Saltline Hotel for the night and was lucky to catch a beautiful sunset.

I stopped in Cannon Beach for a quick walk along the beach and to check out the famous rock. It was crowded with tourists and I could see why, Cannon Beach felt like it was straight out of a movie with its shops, manicured gardens, and seaside homes with stunning ocean views.

I stopped briefly in Depoe Bay to check out the views and grab some coffee. Wow what amazing vistas!

My final stop was Newport where I had dinner by the waterfront where all the locals enjoy amazing seafood.

My favorite coastal towns along Highway 101 were Seaside, Cannon Beach, Depoe Bay, and Newport! Thank you Oregon, my neighbor to the north, for showing off your scenery!

My  trip to Oregon had highs and lows. Travel isn’t always rainbows, but knowing that I still do it for the new experiences and vistas. Travel always teaches me something and I come back with stories to tell, like the motel where I was scammed! I made the mistake of not checking reviews and ended up at a total dump that used fake pictures to advertise and had no room available when I arrived. Thankfully I got my money back but that wasn’t a pleasant experience.


This road trip was a solo adventure. I’m lucky that Matt is the kind of person to say to me “go, explore, have fun!” while he handles the family obligations. When I travel solo I have a lot of freedom and solitude and I gain clarity being alone with my thoughts. I also have an opportunity to meet locals and strike up conversations with strangers I might not talk to if I was traveling with others.

Exploring new places makes me feel alive, and I always return from a solo trip as a relaxed, inspired, more evolved version of myself.


  1. Solo travel is somewhat underrated. I haven’t done a lot of it, but aside from business travel I did go to Bali alone from Singapore for a week and like you, one of my favorite experiences was white water rafting. And yes, it offers you the opportunity to meet people you otherwise might not if you have the ‘comfort’ of a travel companion.

    I’m not surprised Portland didn’t impress, but also not surprised the smaller towns did. I’ve learned cities are not my thing and much prefer nature and quirky, small towns.

    I notice your travels rarely include Matt. Is he unable to get away, or does he dislike travel?

    • I agree solo travel is wonderful!
      Sadly we have no childcare and two busy teens in school so solo is the only option but I have great travel friends too.

  2. I love each and every one of these photos!! Makes me want to put Oregon on my bucket list!! Do you mind if I ask what camera you use for travel? I have a Nikon D7000 but it is sooo heavy that it almost feels like a burden taking it on vacation. Do you have a camera that you recommend for road trips/travel? thank you!

  3. We did part of that trip in 2019 but in October. We were in Depoe Bay during a storm! Wow was that an experience as the waves break right up to the road!

  4. Wow, I am surprised these photos came from an iPhone!
    What makes them great is your composition skills and appreciation of color and perspective and a steady hand.
    Ok I’m going to keep trying with phone photos. I think I’ve been too hasty with setting up shots cuz I thought the quality would be low anyway.
    I’m with you, solo travel is awesome, as well as solo in-town outings. Everything is so spontaneous and focused. I like planning a trip without constantly wondering if some other person is going to enjoy.

  5. I love your travel posts! Thank you for taking the time to take the photos to share with us. I have heard how beautiful the Oregon coast is, and hope to make it there one day.

  6. Loved your post. My son lives in Portland, he moved from outside the Philly area back in 2017. In 2019, my husband and oldest grandson flew out for a vacation there. Our first trip there. My son took us to many of the places you saw in Portland, along the coast in Astoria, and even that Maritime Museum. Have some of the same pics from our trip. Thanks for sharing, it brought back memories of a happier time for us.

    My husband suffered a catastrophic, severe spinal cord injury the last day of our vacation there. We were stuck in Portland for 8 weeks until I could get him back to the Philly area, where a short time later he died of complications.

  7. My husband and I did an epic road trip from San Juan Islands all the way down the coast, including Astoria and Hood River as well. Now I’m antsy to go back! This all looks BEAUTIFUL and of course, like any place, you can never do it all in one trip. The nature in the PNW is such a different vibe from the rest of the country, really incredible to see in person.

  8. Your photos are incredible! The one of the swings is really cool. I have family in OR and have made lots of trips there but I’ve added a few of your ideas to my list. Thank you!

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