Kel and I had already taken a road trip along the Oregon Coast. On this spring visit, we followed a different route: south from Portland through the Willamette Valley and Eugene, ending in Medford and the Rogue Valley.
The trip grew from one of Kel's work trips. While she worked, I explored on my own. When she was free, we got back in the rental car to see what was next.
We had five full days to explore, bookended by flights. That week included a Japanese garden and redwoods in Portland, an enormous historic airplane, a winery lunch, a quick stay in Eugene, and a couple of days in Southern Oregon wine country.
Starting in Portland
Sunday was for travel. We flew from Austin to Portland via Denver, picked up a rental car at the airport, then went to dinner at Gado Gado before checking into The Benson downtown.
We had stayed at The Benson once before. Its history, location, and value brought us back, and it made a convenient base for our short Portland stay.
Kel worked Monday, so I set out on my own. After coffee at Less & More Coffee and pastries from Ken's Artisan Bakery, I headed to the Portland Japanese Garden.
It was 53 degrees, cloudy, and breezy, a pleasant chill for walking. The garden was busy, but I slowed down to take in its layers of color and texture.
Waterfalls, rock gardens, koi ponds, and birdsong appeared between the trees. I've visited several Japanese gardens in the United States, and this was one of the best I've seen, perhaps the best.
I wasn't ready to leave when lunchtime came, so I stopped at the garden's Umami Café for a tamago sandwich, hojicha tea, and a small flower gelatin dessert. The café is inside the garden, so you need garden admission to visit it.
From there, I caught the free Washington Park shuttle to Hoyt Arboretum where I followed the roughly 0.9-mile Spruce, Wildwood, and Redwood trail loop, passing the Wedding Meadow and stopping at the Redwood Deck.
Standing among those trees brought back memories of my visit to Armstrong Redwoods in California.
I spent the rest of the afternoon nearby with a self-guided visit to Pittock Mansion. Then I met Kel for happy hour at the hotel bar, and we had dinner downstairs at Honorable Mention.
Portland to Eugene: Donuts, Airplanes, and Wine
We checked out at 6:45 a.m. Tuesday and picked up Blue Star Donuts on our way out of Portland. About an hour later, we reached the Evergreen Aviation & Space Museum, arriving for its 9 a.m. opening.
The main reason for our stop was the Spruce Goose, the enormous wooden airplane Howard Hughes built and flew only once. Seeing it in person was worth the detour, and we spent time with the museum's other historic aircraft before continuing south.
Our next stop was Sokol Blosser Winery in the Willamette Valley. We booked a tasting and planned to have lunch there, but our visit turned out to be more generous than expected.
After I mentioned in the reservation that I intended to write about my experience, the winery provided our tasting and butcher's board free. They also gave me an impromptu tour and two small library pours.
The board included cheeses, cured meats, local hazelnuts, marionberry jam, and apple-pear mostarda. Of the wines in my regular tasting, the 2024 Croft Vineyard Sauvignon Blanc was my favorite and the one I would consider buying. The Pinot Gris was more assertive than I like.
What I remember most, though, is how welcoming the team was. Jared guided our tasting, and Aaron, the event manager, showed us around.
We arrived in Eugene around 3:45 p.m. and checked into the Holiday Inn Express & Suites Eugene Downtown. That evening, we went to Bar Purlieu for a French dinner of oysters, scallops, duck, and pistachio butter pie, accompanied by a soundtrack of 1960s and '70s songs.
A Short Stay in Eugene
I had less than a day to explore Eugene before we continued south. The next morning, while Kel worked, I got pastries and coffee, walked by the Willamette River, and visited Skinner Butte.
I also made time for ice cream, takeout for lunch, and the Cascades Raptor Center before picking her up. That is the short version. I wrote a separate 24-hour Eugene food guide with the meals, stops, and small detours that made up the visit.
By late afternoon Wednesday, we were back on the road. The drive to Medford took us about two and a half hours, and we arrived around 5 p.m.
Ending in Medford and the Rogue Valley
Medford was our base for the final part of the trip. I had been looking forward to exploring a wine region that was new to me, and over the next two days we visited DANCIN Vineyards, Edenvale Winery, and Ravissant Cellars. We also spent a little time in Jacksonville, a historic mining town.
Each winery gave us a different place to pause: a patio beside a koi pond at DANCIN, roses and a pleasant breeze at Edenvale, and a seat under a cherry tree overlooking the vines at Ravissant. The last was my favorite spot of the trip, and 90 minutes there felt too short.
I've covered the visits, wines, and food in my Rogue Valley wine tasting story. For this road trip, Medford worked well as the final base: we could explore the area without changing hotels again, then fly home from there.
We checked out at 5:30 a.m. Saturday for a 7:35 a.m. flight via San Diego to Austin. Returning the rental car at Rogue Valley International-Medford Airport was easy, a welcome ending to an early travel morning.
Would I Take This Route Again?
Yes. I'd make more time for Portland and the Willamette Valley if our schedule allowed, but I liked how varied the trip felt. The museum and winery gave us reasons to stop between Portland and Eugene. Eugene deserved the time we gave it, and Medford opened up a wine region I'd gladly revisit.
If you're planning the same route, I'd choose a few stops you genuinely want to spend time in and leave room around them.
For me, the moments that lasted weren't just the destinations on the map. They were a cool morning in the Japanese Garden, a walk beneath redwoods, a welcoming afternoon at Sokol Blosser, and the still view from under a cherry tree in the Rogue Valley.
