While we could have easily stayed busy the whole week we were in Portland, OR, we decided to rent a car and take a road trip for a few days.
Day 1
I took an early Uber to the airport to get a rental car, then headed back to our hotel to pick up The Husband, The Best Friend, and Her Wife.
Of course, our first stop was for coffee. We decided to try somewhere new and stopped at Haven Coffee Company. Like the basic B that I am, I had a pumpkin spice iced latte and it was delicious.

Fueled up, we continued on to our first actual stop, Cannon Beach. If you’ve searched Oregon on Google or social media, you’ve seen Cannon Beach. We decided to stop at Ecola State Park first, so we could see Cannon Beach from above. The uninterrupted coastline, the Pacific Ocean as far as you could see, and the incredible rock formations jutting up out of the water were breathtaking.
It’s also known as a filming location for parts of the cult classic The Goonies.




While we all could have stayed there forever, we had to keep moving. We headed down to Cannon Beach. We started at the most famous spot: Haystack Rock. It was slightly chilly and the wind was blowing, which was perfect for the vibes.
It’s hard to tell, but Haystack Rock is HUGE. The scale is impossible to understand from photos. Like most of Oregon, it was incredible to see in real life.



After walking the beach for a while, we stopped for lunch at Pelican Brewing Company. It was convenient to Cannon Beach, had a parking lot, and a nice variety of options.



After lunch, we headed to Hug Point Beach. The Husband read that it had beautiful views and a waterfall. The views were as beautiful as promised, the rock formations were gigantic, but the waterfall was practically dry.




The next stop was the one we were collectively most excited for—Tillamook! As lovers of cheese and ice cream, we knew we couldn’t go to Oregon without stopping there. And it did not disappoint.
When we arrived, we started by taking a self-guided tour of the production floor. The setup is pretty cool—you head upstairs, get some cheese samples, then watch them make cheese and ice cream below through huge observation windows. And it’s free!




After learning more than we needed to know about dairy production, we headed downstairs to get some ice cream. They have tons of flavors, including ones only available at the creamery. We ended up getting three flights so we could try multiple flavors. There were all my favorite.

High on ice cream, we decided we didn’t want to miss out on trying their pizza. Despite none of us being hungry, we ordered a whole pizza and saved it for later.

Fat and happy, we got back in the car and headed to our final stop for the night, The Holman Hotel in Salem, OR. The capital city (town?) had very little going on. So we checked into our hotel, walked around a bit, and returned for dinner at their restaurant, Gamberetti’s Italian Restaurant. Everything was fine, but we only stayed there because it was close to Silver Falls State Park.



(Literally the only photos I took in Salem)
Day 2
We headed out early the next morning. We stopped at Isaac’s downtown for coffee and breakfast, then headed to the Trail of Ten Falls in Silver Falls State Park.



The trail is an eight-mile loop with (you guessed it) ten waterfalls. Luckily, there were shortcuts so we didn’t have to do the whole thing. The Husband and I ended up doing a five-mile hike and seeing seven of the waterfalls. It definitely wasn’t easy, but it was worth it. (Full details coming on the next blog post.)






After eating leftover Tillamook pizza in the parking lot, we started the drive to Bend. We rented the cutest Airbnb, and it was such a relief to be somewhere comfortable for two nights. It was right in the heart of downtown Bend, which was way cuter than we expected.




For dinner, we headed to Deschutes Brewery Public House. The Husband and I enjoyed appetizers there so much in Portland that we wanted to go back. The food was fantastic, but the Brussels sprouts were the star of the meal.




We slowly meandered back to our Airbnb. We stopped at Amaterra for a wine tasting and cocktails. It was fun to have cocktail drinkers with us, since I would never pick it over red wine. That way, I got to try their drinks and still have what I wanted. And everything was delicious.


We came across Bonta Gelato and decided it was time for dessert, even though none of us were hungry.

We waddled back to our Airbnb with full intentions of retiring for the night. But a collection of buildings across the street piqued our interest. Turned out it was McMenamins Old St Francis School, an old Catholic schoolhouse that was converted into a hotel, with bars and a brewery. It’s a super cool spot.
We also learned about the Broom Closet, a speakeasy-style bar that we just had to check out. We went through a secret door into a “broom closet” passageway that opened up into a bar. We had a quick drink, then headed home.




Day 3
We originally planned to go to Crater Lake, but the Crater Lake National Park webcam showed very low visibility. We decided it wasn’t worth the drive if we couldn’t see the lake. Instead, we spent the morning walking along the Deschutes River. Everything was so green and beautiful. We stopped for lunch at Bend Brewing Company before walking away from the river to Blockbuster.




Yes, Blockbuster. The last Blockbuster standing is in Bend, OR, and you can still rent movies! They also have a great selection of memorabilia. It was definitely worth the long walk from downtown. You can read the full review here.




Of course, I needed to get my bookstore fix. First, we stopped at Big Story Bookstore. They had a great selection, and their logo is an owl, so obviously I loved it. Then we stopped at Dudley’s Bookshop Cafe, which also had a great selection and delicious coffee, and Pegasus Books of Bend, which sells primarily comics and graphic novels.



We stopped at Cravin’s Candy Emporium, because who doesn’t like old-timey candy in an old card catalog?

Our last stop before heading to dinner was Bend Whitewater Park, to watch people river surfing (like in Munich).

Our last stop in Bend was Ken’s Artisan Pizza for dinner. We weren’t sure if we would get a table for Monday pizza at the location in Portland (but thankfully we did) so we went to the location in Bend. Unsurprisingly, it was delicious.

Day 4
We packed up our stuff and began the drive back to Portland. Our first stop was Trillium Lake, and the view of Mount Hood. It was so peaceful, and the view was unmatched.

We had a quick lunch at Mount Hood Brewery, the only non-chain, non-fast food option on our route. It wasn’t worth a special trip but it was fine.
After lunch, we happened upon the North American Bigfoot Center in Boring, OR. It’s a whole ass museum dedicated to “proof” that Bigfoot exists. As a lover of conspiracy theories (hearing them, not believing them), I was enthralled. The museum was well-done and almost made believers out of us.





Our final stop was Multnomah Falls. At 620 feet, it’s the tallest waterfall in Oregon. Part of the Columbia River Gorge, there are trails and multiple waterfalls, and you could spend hours there. Parking is impossible (only 200 spots), so if you go in the peak season, consider taking a tour or bus. We got a spot relatively quickly considering. The best view of the falls is right next to the parking lot, so we were in and out pretty fast.

Then we headed back to Portland for our final days there before The Husband and I headed to Utah.