I’d longed to visit Portland, Oregon for years, hearing rave reviews of its hipness and natural beauty. Through a series of odd (yet delightful) opportunities, I was able to do a whirlwind tour of the city before driving out to Bend, OR on Route 26 — then back to Portland via Route 20.

What was revealed is that the highways that stretch from Portland to Bend Oregon, are every bit as fabulous as the destinations, themselves. Come take a tour of the two routes!

Route 26 From Portland to Bend, OR

Route 26 is a joy to drive. As a child of the northeast (Boston-raised, with petite Mount Greylock being the tallest hill around), imagine my ecstasy at first glimpsing towering, snow-capped Mount Hood as it peeked around the bend of Route 26! Luckily, there are several scenic overlooks with safe shoulders to pull over on, and I took full advantage of that to snap the photo below.

Route 97 and Culver, Oregon

Further along the northern journey from Portland to Bend, you’ll turn from your eastward Route 26 path onto Route 97 heading south. At that point, don’t miss the Peter Skene Ogden State Scenic Viewpoint right along the drive through Culver, Oregon: the overlook onto Crooked River High Bridge and the Rex T. Barber Veterans Memorial Bridge will take your breath away!

Crooked River High Bridge Warnings

Just make sure to take the cliff warning sign pictured below seriously. A 300-foot drop into the gorge of Crooked River near the bridge would be… awful. I was reminded of the danger signs at the Newport, RI Cliff Walk: The stick figures hurtling off the edge look comical, but it’s no laughing matter in reality.

Peter Skene Ogden State Scenic Viewpoint

You can spend just a few minutes at the Ogden Viewpoint (it’s convenient that it’s right off the highway), or take much longer to walk the paths along the bridges. As you stroll the area, you may notice something…

Oregon: Half Lush and Green, Half Desert

What I didn’t realize until doing the drive from Portland, OR to Bend is that the west of Oregon is the classic lush greenery that I associate with Pacific Northwest destinations like nearby Seattle, Washington — but the eastern half is desert! The town of Bend sits in the middle of those opposing forces (though more in the leafy green side), and this drive takes you through each.

Dry and Arid Oregon?!

The stretch of Route 97 (and Route 26 right before it) around Crooked River reminded me of a moonscape, parts of it are so dry, arid, and rocky. Oh, and don’t get confused — I’m talking about desert, not dessert. We’ll talk about yummy dessert in a few paragraphs, never fear.

Route 97 continues through the towns of Terrebone, Redmond (where there was a fire raging nearby, the day we drove through), and right into Bend. Because I spent a few days in that town, here’s my round-up of articles about it…

Bend to Portland, via Route 20

Enjoyed Bend and ready to head west again to Portland? To mix things up, we used the southern route for our return trip, taking Route 20 through stunning forests, mountains, rivers, lakes, and old-fashioned Wild West towns.

Sisters, Oregon

Speaking of old-fashioned Wild West style towns, Sisters, OR fits the bill! I felt like we should be pulling up in a stagecoach instead of a modern rental car. I was particularly enraptured by the log furniture shop, as well as the general store that was packed to the gills with wind chimes and lawn decorations, pictured below. Stop by Sisters, Oregon for all your pressing flamingo statue needs!

Detroit Lake, Oregon

An hour and a half east of Bend on Route 20, tall, thin trees tower above, and azure Detroit lake sparkles. I was reminded of Devil’s Lake near Bend — but also a little bit of Ha Long Bay in Vietnam! I could imagine a wonderful getaway trip here of several days, frolicking in the water and through the forest.

Which Portland-Bend Route is Better?

I really enjoyed both routes between Portland and Bend, OR, so it depends what you’re seeking, if you’re choosing between the two. The northern one, Route 26 to 97, is more direct and faster, and goes through more of the desert regions. The southern one, Route 20, has splendid mountain, forest, and lake views, and is very natural and wild. In an ideal world, do both routes like we did!

Back in Portland from Bend

Returning to the bustle of Portland after days in tranquil, nature-soaked Bend was a bit of a culture shock. The delicious food and sights soon soothed, though. Even the streetcars in Portland are jolly!

Temperatures in Oregon

This visit — the summer of 2021 — was during the historic Pacific Northwest Heat Dome, and so usually cool-weathered Oregon turned into an oven. Check out our rental car temperature gauge pictured below: 114 degrees Fahrenheit!!! Needless to say, the car came in handy when it was too scorching to walk outside. Thank goodness for scenic drives.

Edible Cookie Dough?!

Given that ice cream would melt in this scorching heat, I opted instead to head to The Cookie Dough Cafe in Portland for some edible cookie dough: a delicacy I discovered in Portland which I’d never before encountered. Below, ogle three different flavors: brownie batter, chocolate chip, and Snickerdoodle! It was darn good, and I wish Boston would get a store like this.

Thanks, Portland and Bend!

I highly recommend a trip like this which combines Portland and Bend, OR — all while enjoying the road journey, which is a destination unto itself! Have YOU been to this part of Oregon, or any other part? If so, what was your experience like? Do share!

Want to extend your Pacific Northwest fun? Take the Amtrak train north from Portland to Seattle as I did to check out the beautiful colored glass Chihuly Seattle, WA exhibit!