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Two-Week Road Trip Through Oregon with Friends: Part 6

  • Written by Lindsey Huster
  •  / 
  • 9 min read
  •  / 
  • Last updated 5 months ago

This two-week trip through Oregon consisted of meeting friends from our hometown in Indiana at the Portland airport. We picked up a rental car and headed out to explore a large portion of Oregon together. We drove down the coast and into California to Redwood National Park before heading inland to Crater LakeBend, and Columbia River Gorge, to name a few highlights. Essentially, a loop covering significant points of interest in Oregon.

Thoughts About this Trip

It was surreal to think about everything we had done in those 2 weeks. At times the trip seemed like it was months long with everything we were able to pack into the itinerary. In other moments, we wished there was still more time together. Jason and Kristen are not only great friends, but they are excellent friends to travel and vacation with. We love spending quality time together, exploring new places, and making a ton of memories together ❤️

Highlights Along the Oregon Coast

The first day was everything I had built up in my head. Reaching the Oregon coast and walking in the Pacific Ocean in Cannon Beach was just how I imagined it. The chill in the air, the cool wind on our hair, the salty water, and the fine sand on our feet. Stopping at Pelican Brewing for a seafood dinner before heading to our beachfrom hotel topped off the day.

My favorite beach wasn't exactly a beach at all. Cobble Beach consists of black rounded rocks that make the most magical sound as the water flows between the rocks and recedes knocking the rocks into each other. I felt like I was the only one there as this sound drowned out all other sounds.

Iconic stops like walking the boardwalk to Rockaway Big Tree, touring the Tillamook Creamery, and standing near Devil’s Punchbowl were all reality now. Things I could check off the long list of this trip. It was exciting to see the plan come to fruition and see these locations with my own eyes.

This just continued that first week with whale-watching in Depoe Bay, walking around Devil's Churn, watching photographers at Thor’s Well, laying eye on the Heceta Head Lighthouse, smelling the famous Sea Lion Caves and so much more.

Another big highlight for me was stumbling up the sea lions at Cape Arago South Cove. We thought this would be a short walk to stretch our legs, little did I know this would be one of my favorite stops. We had been looking right at the sea lions, not seeing them. All of a sudden the noise and their location were put into focus and there were several lying just below us on some rocks relaxing. There was another large group on a rock island further out. These were the rambunctious bunch and seemed to be “yelling” at one another and playing. This was a great surprise.

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Highlights of Southern Oregon and Northern California

Redwood National Park is absolutely stunning and unbelievable until you are there. Upon entering the park, we had to stop the car, get out, and see these giants without the constraint of a vehicle.

Hiking Grove of Titans had our jaws dropping and each of us in our own worlds trying to comprehend the size of these massive trees. Continuing with Stout Grove, Simpson Reed Memorial Trail and Ellsworth Loop Trail gave us more time to explore and experience this magical place.

Endert's Beach wasn't even on our itinerary and is exactly the reason you need to chat with people, especially park rangers. I had high hopes of sea life on this trip and I had no idea how abundant it could be. We had seen a couple of starfish earlier, but arriving at this beach I had no idea what we were in for.

Massive tide pools lined the beach bursting with invertebrate life; mussels, starfish, sea anemones, etc. We were all in amazement at the sheer number of sea creatures on the beach. We continued to walk along and there were just more and more of these tide pools. It was so exciting and I knew immediately this would be the highlight of the day and probably of the trip for me.

Visiting Crater Lake National Park, hiking Cleetwood Cove Trail and putting my feet in the lake was something I had been looking forward to for quite some time. This was probably the second most memorable part of the trip for me.

It was early morning, the air was crisp, and walking down the dirt trail was exciting. The switchbacks offered different views of the lake and once you reach the water bank, there were boulders to navigate to the water's edge. Sitting on the boulder and putting my feet in the water was something I was excited to check off my list.

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Highlights from Interior Oregon

Touring around Bend was an amazing experience! This area has a lot to do and the kind of place we could spend more time. The Deschutes River offers a pretty view and outdoor recreation. The Old Mill District is a relaxed area to shop, eat, and just hang out outdoors. Nearby skiing, museums, parks, and more make this an ideal location to visit. Continuing our drive back to Portland was filled with interesting stops. The giant troll named Olebolle was a fun spot.

Our time at Timberline Lodge was another true highlight. Exploring the lodge was better than I imagined. I loved the rustic look and the furniture was interesting to me. Lots of sitting nooks I could imagine myself enjoying after skiing, hiking or just vacationing. We took some needed relaxation time indoors and outdoors to take it all in.

Mount Hood kept us searching for times it would be viewable. It was quite cloudy, but we got a couple of peaks at Trillium Lake Dam. Eventually, we got another great view after driving around and exploring a trailhead.

An entire day chasing waterfalls was exciting and offered beautiful scenery at every stop. Each waterfall was special in its own way. The mix of hiking, walking, and basically reaching the waterfall just after a parking lot stroll helped us to keep momentum and allowed us to see a big portion of what is known as the "Waterfall Corridor."

Our first waterfall, Wahclella Falls, was definitely a highlight of the day. The 2.4-mile (3.86-kilometer) hike included canyon views, bridge crossings, and a little boulder scrambling. It was well worth the effort.

Multnomah Falls is not only iconic but quite impressive to see in person. If I had to repeat this, I'd probably spend a little more time here. Maybe grab a treat at the snack bar and sit to enjoy the waterfall or give the restaurant a try. It's a busy area, but probably worth the hassle.

Latourell Falls is another one that sticks out in my mind. The height and color contrast are just unforgettable. Walking up to the waterfall and taking pictures was so much fun. The splashes of the water took away all other sounds and felt so peaceful.


I am so thankful Keith and I had the chance to explore Oregon. Any time we travel, we learn so much, have memorable experiences and our worldview expands. So many times in the months since this trip, Keith and I have referred to a specific adventure, location, or other memory from this vacation.

The very best aspect of this trip was traveling with friends! Do you travel with friends? Tell us a great location for a friend's trip. Let us know in the comments section below.👇 💬

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