Portland and Nearby Oregon 2026

Trip Introduction

In June of 2026 we decided to take a trip to a portion of the Pacific Northwest neither of us had visited previously. We flew into Portland, Oregon and visited several areas on the western side of the state over the next 10 days.




Saturday, 6/13/2026 – Westward(ish) Ho

Our flight out of Des Moines wasn’t until later in the afternoon so we finished packing in the morning and had an Uber take us to the airport around 2:45p. We had booked the west bound flights using airline miles, which meant the low-cost route took us through DFW near Dallas. Our flight south left about 20 minutes late, but our layover was 2 hours, and we made it in plenty of time. We had been watching all afternoon as the departure gate for our flight to Portland jumped around, but when we landed it was only a 10-minute walk between gates. The flight was also listed as being delayed a little over 30 minutes, so we had plenty of time to find something to eat before boarding. As a bonus, somehow, we jumped to the top of the upgrades list and ended up getting First Class seats on a flight we didn’t pay for. Once the plane arrived and we boarded, we sat for a while. The captain eventually explained that one of the passengers needing wheelchair assistance had been brought over without his personal wheelchair. There was apparently concern about time between flights and a representative of the airline promised to get it over to the gate before departure. With the inbound flight arriving late, this apparently happened and the wheelchair was sitting on the gangway when the previous flight’s passengers were unloading. Someone sat in the privately owned wheelchair instead of one of the airport-provided chairs and the person there to help them didn’t bother to ask if it was actually theirs. What resulted was the wheelchair owned by the person on our flight made it all the way to the curb where the other passenger transferred into a car and left it sitting there. Fortunately, the crew of our flight identified the problem before we took off. After an additional delay of about 30 minutes, the chair was located and made its way back to our plane. The result of all this was instead of landing at PDX a little before 11p, we landed just before midnight. After waiting for our checked bag and the hotel shuttle, we arrived at the hotel to be told they did not have any available rooms matching our single, King bed reservation. They did have a two Queen-size beds room and at that point we really didn’t care. We finally arrived at our hotel room at 1a Sunday morning to find 2 full size beds and promptly changed clothes and crawled into one of them.




Sunday, 6/14/2026 – Driving South to Hill Country

We left the room a little before 8:30a. We had reserved a car but didn’t want to pick it up late Saturday to pay for it to sit in a hotel parking lot overnight. James took the hotel shuttle back to the airport and made his way to the Budget Fastlane area where he had been told his car would be waiting. The vehicle in the identified spot did not match the notification he received (Chevy Tahoe does not equal Subaru Forester). As he looked around, he realized the car with the license plate he’d been sent was sitting across the aisle in row E facing the row D spot he’d been given. He returned to the hotel to pick up Julie and the luggage before heading south out of Portland. We stopped at an outlet mall to see what the Clark’s shoe store had available and walked around visiting several other stores. We needed to kill about 3 hours before heading to our next stop. The highs were supposed to be in the mid-90s, very hot for the area in June, and temps were in the upper 80’s as we walked around in early afternoon. After leaving the outlet mall, we made our way to The Oregon Gardens in Silverton. This is the current location of the only Frank Lloyd Wright designed house built in the state. The house was relocated to its current site when new owners of its original site planned to demolish it in the early 2000s. The Gordon House is one of his late Usonian Houses designed just 18 months before the architect’s passing and not constructed until several years later. The original owners lived in the house until their deaths, the wife’s being in the late 1990s. In addition to the unique scroll work typical of each of Wright’s Usonian homes, this house was also unique in that the living area had glass on both sides. On its original site, one side would have looked over a river while the other had a view of Mt. Hood. We enjoyed the tour, which was less detailed on Wright’s work than usual since we had already visited several of his homes and were 2 of the 3 people on the tour.

Once the tour wrapped up around 3p, we headed farther south to Oakland where we had reserved a VRBO. When we arrived, a little before 6p, we were surprised to find two cars parked at the property. James opened the door to find food on the counters and could clearly see open luggage in the bedroom. Nobody answered when he called out so he left the house and called the management company. They contacted the Owner whose father lives adjacent to the two tiny homes around an old mill pond. As the father was on the phone, another car with 5 people pulled up. After several minutes of back-and-forth between the other family and the owners, we learned that a couple from Britain had arrived the previous Wednesday and occupied the wrong unit. When this family showed up on Friday, they took the unit the British folks should have vacated today for us to check-in to. We could either make the other family pack all their stuff and move, or we could take the other unit. The plans were similar, but the one we reserved had a few nicer features. That being said, we didn’t want to wait for them to move out and then have someone come clean the place so we said we would look at the other unit and if we thought it would work, we’d just stay there. What we discovered when looking at the other unit was it had not been cleaned after the other couple departed early in the day. So, we left to go get something to eat and see what was actually open in a small Oregon town late on Sunday evening. We returned to the property around 7:45p to have the cleaner show up 5 minutes later and let us know it was going to be another hour before he finished. We sat around the property for a while before heading into nearby Sutherlin for some toiletry products we realized were not provided and finally unloaded the luggage into the unit around 9:15p.




Monday, 6/15/2026 – Windy Roads and Calm Waters

We left the tiny house around 9a and headed back to Sutherlin for a bite to eat. From there we headed southeast on country roads to visit Crater Lake National Park. The drive was a little over 100 miles but took two and a half hours because of the windy roads and a few spots where construction reduced a mile or more of the two-lane road down to one. There were several scenic overlooks along the way, but we only stopped at one near a bend in the North Umpqua River. We reached the park via the north entrance and approached the rim from the northwest. Crater Lake sits in the caldera of an old volcano. While the temperatures were again warm, there was little wind in the early afternoon, so the water was very smooth creating incredible reflections of the cliffs and hills that form the sides of the lake. We spent a couple hours stopping at various viewpoints around the west and south rim taking a lot of pictures. James even had a butterfly ride on his hat for about 5 minutes at one of the stops. We couldn’t drive the full loop because the southeast section of the rim road was under construction and the north side still hadn’t opened after the winter closure. While temps were in the mid 80’s, there were still sizable patches of snow in a few areas. We elected not to stop and take a picture in the snow, though it was popular with many of the visitors.


We headed out of the park through the south entrance knowing it was going to be a longer route back to our accommodation but not wanting to back-track around the rim road. There was not much traffic as we went along the tree-lined roads. We stopped at one viewpoint along the Rogue River Gorge and were able to see some very powerful rapids and waterfalls running through the narrow valley. After that, we ended up on some very windy roads through what felt like a mix between Maui’s Road to Hana and the Mt. Rose Highway south of Reno. After almost two hours covering a little over 50 miles, James was happy to see the interstate where he didn’t have to slow down every couple of hundred feet to turn a corner. We stopped for an early dinner in Roseburg before returning to our rental to rest for the evening.




Tuesday, 6/16/2026 – A Day of Rest

Tuesday, we slept in and didn’t leave the VRBO except for an afternoon walk and to get something to eat in the evening. We spent the day doing what you should always do at some point on a vacation: discussing your next one or two vacations. It was good to relax. In the evening we organized our luggage for the next leg of our journey which would take us to the coast and back north.

Image One
The tiny house on the millpond where we stayed in Oakland



Wednesday, 6/17/2026 – A Drive Along the Coast

We packed the car and left the VRBO around 8:30a. We headed through the Oregon Coast Range of the Cascades following the Umpqua River toward the Pacific Ocean. Once we got to Highway 101, which runs the full length of the coast, we turned north stopping several times along the way for either food or photos. The drive was nice, but as we got further north, the coast was more developed and traffic became consistently heavier. We arrived at our Bed & Breakfast in Seaside right at 4p. After checking in and unloading our stuff, we walked the block to the promenade the runs along the beach. We enjoyed the cool breeze off the ocean under the bright sun. We walked the main tourist shopping street and returned to hotel to rest before having dinner. We decided to head back to the beach a little before sunset to watch the day end over the Pacific Ocean.




Thursday, 6/18/2026 – A Train and Cheese and Ice Cream

After breakfast at our B&B, we packed the car and headed out around 9:30a. This gave us plenty of time to stop along the coast and take pictures as we made our way south out of Seaside. Based on a recommendation of a vendor James was working with, we visited the Blue Heron French Cheese Company. They had a nice shop, and we enjoyed lunch from their deli. We then made our way back north a few miles to Garibaldi for our 2p departure on the Oregon Coast Scenic Railroad. We enjoyed the scenic roundtrip trip to Rockaway Beach and back. After returning to the car, we made one more stop near the coast at the Tillamook Creamery. We enjoyed the self-guided tour where we learned how they make and package cheddar cheese. We also enjoyed a flight of three different flavors of their ice cream. We waddled back to the car and headed away from the coast and into Portland. We timed things so we arrived after rush hour and checked into our hotel a little after 7p. We decided to unwind for the night with a light dinner in our room.




Friday, 6/19/2026 – Waterfalls and Mt. Hood

We had booked a tour up the Columbia River Gorge stopping at several waterfalls and heading to Mount Hood for Friday. Our guide picked us up outside the hotel just before 9a and after one more pick-up the guide took the 13 visitors out of the east side of Portland. The guide told stories about what we were seeing the entire time, and it was very interesting to hear about the history of the scenic highway along the gorge. Our first stop was at the first welcome center built as part of the highway construction, Vista House at Crown Point. It was meant to be an attraction, so it was very ornate and the views were spectacular. Our next stop was at Latourell Falls. It was a nice area with views of the falls at two different levels. We then headed to Shepperd’s Dell with a multi-level waterfall that then ran under an arched bridge. The last of our waterfall stops was at Multnomah Falls, which is the third highest in the US. When you search for sights to see in Oregon, images of these falls are often near the top. There is a tall section and then a lower fall with an iconic arched bridge visitors can get to via a winding paved trail. We enjoyed the stop and visit to the visitors’ center and gift shop. Our guide then took us up I-84 to Hood River where we had time for lunch. We shared a table with another couple on the tour at the outdoor seating area of Full Sail Brewery where we tried a new dish, Salmon Fish and Chips. After our lunch stop, we headed away from the gorge entering what is known as “The Fruit Loop.” Our guide took us to a family-owned fruit stand that had a wide variety of jellies, baked goods, and other treats. The stand also provided an exceptional view of Mount Adams in southern Washington. We all piled back into the van and headed to our final stop, Timberline Lodge on Mount Hood. Some might recognize it from the Shining as it was used for the exterior shots of the Overlook Hotel. It is located at approximately 6000 feet above sea level where the pine and fir trees give way to stone. Both the views over the surrounding forests and the architecture of the historic lodge were stunning. Our last leg of the journey brought us back into Portland returning to the hotel around 5:30p. We spent the evening relaxing in the hotel.




Saturday, 6/20/2026 – Stepping Around Downtown

Our plan for Saturday was to visit some of the sites in downtown Portland. We left the hotel around 9:45a and made our way to The Saturday Market. After walking through the stalls looking at the many different crafted items, we headed to Pioneer Courthouse Square. There was an event where kids could race through several inflatable obstacle runs and we sat for a few minutes watching them enjoy the event. Like we had in Boston, we pre-purchased a quest from Urban Adventure Quest. This took us around downtown seeing various points of interest from building art, sculptures, and important city sites. After three hours of solid walking, we were perfectly happy to sit and have a sandwich for a late lunch. Our next stop was at the largest independently owned bookstore in the world, Powell’s Books on Burnside. With around 1,000,000 square feet of bookshelves on three levels, they have just about everything new or used. We found several used copies of books that were part of series we were reading we had struggled to find in the used bookstore at home. We left discussing how these purchases would impact our luggage situation for the trip home. With an extra few pounds in a backpack, we returned to the hotel to put our feet up. According to our trackers, we walked just under 8 miles (Julie - 18,318 steps or 7.52 miles; James - 17,628 steps or 7.64 miles).




Sunday, 6/21/2026 – Anniversary Gardens

We left the hotel around 9:30a heading to a nearby streetcar stop. Portland has a robust public transportation system, and we used both a streetcar and the regional light rail to get to Washington Park in the hills just west of downtown. This area is home to several attractions including the Oregon Zoo, Hoyt Arboretum, and a couple of war memorials. Our destinations were the Japanese Gardens and the International Rose Test Garden. It was cloudy and cool when we first arrived, but as we walked through the various sub-gardens of the overall Japanese Gardens the sun came out. While the gardens are meant to be a place to quietly contemplate, they are also quite busy, and Father’s Day brought out many families with small children. While we had missed the cherry blossoms by a month or more, the irises and azaleas were in full bloom.

After a couple of hours there, we walked down the hill a few hundred feet to see the roses. There were many rows on a couple different tiers with varieties of all colors and petal count. We spent close to another hour there looking at only a few of the offerings. We decided to take the train back into town and transfer to one of the streetcars to get near a specialty ice cream shop Julie had found. We stood in line for a bit at Salt & Straw but we agreed it was worth it for the strawberry pretzel salad and the sea salt with caramel ribbons. After that we felt we needed to walk the 14 blocks back to the hotel through what turned out to be a nice residential area. We rested for a bit and started figuring out how to arrange our luggage for the flight home. Around 7p we headed out to dinner before returning to the room for the evening.




Monday, 6/22/2026 – Hiding From the Heat

The only thing we had planned on Monday was to switch hotels to one that had a 24-hour airport shuttle and return the rental car. The forecast called for temps in the low 90’s so we ate breakfast as late as possible and stayed at our hotel near downtown until close to check-out time. We then loaded the rental car and drove to Pittock Mansion. On the self-guided tour of the house, we learned about the family who built and lived there, the history of the beautifully restored early 1900’s structure, and the struggle to furnish it when it opened as a museum. The grounds were up on a hill on the west side of downtown and had stunning views of the surrounding valley. It was a clear day, and the heat haze had not set in, so we had a good view of Mount Hood in the distance. After some last photos of the cityscape, we headed back through downtown and found a mall. Figuring it would provide a place to walk around killing time in the air conditioning, we didn’t realize it was a facility in late stages of use. It was clean but had very few stores occupied; the only real signs of inhabitation were at the ice rink in an atrium space. After walking for close to an hour, we decided to head to IKEA for an afternoon snack and to waste a little more of the afternoon. Knowing we weren’t buying anything, except cookies and a chocolate bar, we ate at the cafeteria and walked through the displays. Once we finished there, it was late enough in the day we could check in to the same hotel we stayed at the night we first arrived. After getting settled into the room, James returned the rental car and caught the hotel’s airport shuttle back. We played some cards, had a light dinner at the hotel restaurant, and headed to bed early.




Tuesday, 6/23/2026 – Getting Home

The alarm went off a little before 4:30a so we could make ourselves somewhat presentable and get to the airport and our gate for a 7a flight. Everything went smoothly at check-in and security, so we arrived in plenty of time. The first leg of our journey was a relatively short flight to LAX. We were on a small plane, so we arrived at a smaller remote terminal only American uses and our flight to Des Moines was out of another gate in the same location. We each got a sandwich as the first flight only provided snacks, and our planned 3-hour layover extended by a little over an hour. The good thing about small planes is they can be turned around quickly so we were boarded and took off again quite fast once the plane arrived. We landed in Des Moines right at 7p, only 45-min late. Once we got our checked bag, an available Uber was nearby, and we made it home in time to hit the grocery store for some essentials.




We enjoyed the wide range of scenery and attractions we visited on our first trip to Oregon. We both came back with a little more sun on our skin and having relaxed while away from our daily routine.