High Desert Road Trip: Portland to Bend, Oregon

Tumalo. Metolius. Sisters. Warm Springs. Powell Butte. Mill City. When your eyes scan the map of central Oregon, you will encounter these distinctive place names. Artifacts of the past, the language hints at the region’s layered history — the indigenous river cultures, still very active on the plateau; the native fauna, like white salmon; the early settlements of frontiersmen; the misty days of 20th century logging. 

Other cities, like Bend, have a simpler backstory.  “It refers to a bend in the river,” a woman helpfully explained to me. 

For Spring Break this year, I traveled with my family from the flatlands of the midwest to the very not-flat lands of the Pacific Northwest. I lived in Portland, Oregon for a formative chapter of my life. It’s where I met my wife. Made enduring friendships. Learned to appreciate the endless trails of the Cascades. I’d been hesitant to return, for reasons we’ll come back to, but I also wanted to introduce my sons — Eli, 7, and Cal, 10 — to the mountains and the trees and the food carts that serve only poutine.  

Oregon’s high desert is an ideal location for a holiday with kids. Sunny days. Wild rivers. Cheap food. Lava flows. Outdoor activities in every direction. And a culture where just about anyone will have a friendly conversation with you. Whether that’s what you’re looking for or not. 

For travel, the Pacific Northwest is a relatively cheap flight destination, especially during the rainy season, which is most of the year. Bend has an airport, but you typically need to fly through another city. Alternatively, you can fly into PDX and embark on one of the  country’s great road trips, as we did. 

Portland, Oregon, is well stocked as a road trip provisioning station. Bulk up on snacks and drinks at Wellspent Market in southeast Portland. For coffee and pastries, Lauretta Jean’s, also in SE, has a well-deserved cult fanbase. For a proper breakfast, stop by Bunk Sandwiches, grab a legendary breakfast sandwich and ask for extra Mama Lil’s peppers, a spicy and oily hungarian pepper that is unique to the region. 

Along with LA and Austin, Portland has some of the best food truck culture in the US. Zoning is flexible, which means food carts are plentiful. Portland has over 500 food trucks. A Singaporean I met was not so impressed (they have over 10k stalls), but it’s a strong showing for an American city. Hinterland Bar & food carts in Southeast is good, so is Brooklyn Carreta Bar & Carts, further south in the confusingly named “Brooklyn.” 

Before you leave, walk through the moss-encrusted neighborhoods with your kids. The entire city feels like a terrarium with succulents and odd lawn ornaments sprinkling the landscaping. We found a flop-eared rabbit hanging out in someone’s backyard. The boys fell in love and made a persuasive argument that we should have a bunny in our family. We called the rabbit Floppy Joe and then I swiftly changed the subject. 

As you drive away from the city, ecosystems change rapidly. The urban valley transitions to old growth forests and then high alpine terrain, which then levels out to high desert with clear vistas. Driving up route 26, the profile of the monumental Mount Hood rises from the background, sure to wow your kids, if they’re not already fast asleep. But your ecology lesson will surely be appreciated another time. 

While this is no secret, I can recommend a stop at Timberline Lodge, famously the exterior of the lodge in The Shining. Inside, the scene couldn’t be more different from the movie. Architecture is WPA-era, characterized by raw timber beams and a massive fireplace in the lobby. This is a good opportunity to pick up a hot chocolate and to point out Mount St. Helens on a map, the active volcano to the north that blew up in 1980. In fact, your children should know that most of the volcanoes in the cascades are active, including the one they’re standing on. 

As you emerge from the mountains, the plateau of the high desert is a completely different environment — clear skies, deep ridges, 360° panoramas. This is the exact moment when you should play your (or your kid’s) favorite road trip song. Traffic is sparse and you feel like you’re in a European car commercial, albeit with more food wrappers on the floor of your car. 

Bend is one of the few cities in Oregon’s high desert with any significant population, although at 100,000 people, it’s far from a metropolis. Bend is an isolated oasis, surrounded by harsh desert to the east and a mountain range to the west. You may wonder why the city even exists. 

The main reason is natural resources, namely timber. Trainlines, rivers, and access to forests, all converged to make Bend a hub for lumber processing. Logging has declined, but the population has gone the opposite direction and the city is thriving. Now, the primary export is a very different type of commodity. It’s less about logging and more about lifestyle. 

For accommodations, good Airbnb options abound and I can recommend securing a place in town, which has good walkability. The Old St. Francis School, part of the regional McMenamins franchise, is a charming former school with a campus that features a soaking tub and small taverns warmed by fireplaces.

Air in central Oregon feels different than west of the mountains. Clear, dry, cool air predominates in the high desert. The climate makes it ideal for outdoor activities. At night, the stars are bright and you might consider finding a place to do some dark sky stargazing. The density of outdoor activities is what makes this area unique. Rafting, fishing, skiing, trail running, biking —  all are accessible close to the city. A car is recommended, but destinations are surprisingly close for the American West. To structure an itinerary, you could cluster your activities around ecosystems —  one day on the trails, one day on the mountains, one day in town. Tablets will not be missed. 

For trails, the Deschutes River Trail is very close to Bend and runs all the way to Sun River, about 16 miles south. I can also recommend Shevlin Park which, despite being less than 15 minutes from the city, feels like the backcountry. With kids, I recommend finding an interesting section and letting them explore. The Deschutes River runs smooth and deep in parts, wild and turbulent in others. Waterfalls are in abundance and will enchant kids from less topographically interesting areas. 

We liked the area around Lava Island, which sounds like a missing level from Mariokart. The sharp pumice stone and scattered crevasses were perfectly dangerous. When it comes to hiking with kids, find a spot that is wild and compact. Free exploration is far better than trying to get them to walk to an arbitrary point, only to turn around and walk back. Most kids will thrive if the trail involves throwing rocks in the river or sitting in one spot and looking at the weird stuff under the log. Think micro, not macro. You may enjoy endurance hiking, most kids do not.

Outside of Bend, you can find much more exotic terrain —  the area is bountiful with world-class trails. But if you have city kids, look no further than the Deschutes River Trail or Shevlin. 

Within the vicinity, you will find Mount Bachelor ski resort and wilderness destination. Due to the elevation, quality snow remains until late in the season. We visited in April and encountered zero lines, decent snowpack, and blue skies.

While I am an experienced skier, I am not an experienced ski educator. For much of the day, we skied the easy greens and my kids enjoyed bombing the gentle slopes. Later in the day, they begged to visit the top of the mountain for more challenging terrain. I conceded and found the easiest blue square trail. As we ascended the steep landscape in the chairlift, confidence levels dropped. Are we actually doing these trails? They asked. Yes, that’s the only way to get down. 

Actually, there are two ways to get down. Ski patrol emergency sleds are the other option. So, if you are traveling with overly ambitious boys from the midwest, I would encourage caution on the mountain. We filed this one under “learning experience.”

For a day in town, there are plenty of activities within walking distance. At Bend Whitewater Park, you will find a place to practice kayaking and a perpetual wave for river surfing. Or river falling, which we also observed. In either case, your kids will be entertained for several minutes in a row. Further downriver, Drake Park is a perfect location for a picnic or tubing.

For food, Bend punches above its weight relative to its size. Jackson’s Corner in Old Bend is a solid option for breakfast or lunch. Lone Pine Roasters is the correct choice for those who are serious about their coffee rituals. For dinner, try The Drake, with its generously portioned plates. You will also find a growing food cart scene. Podski has a cluster of options — Cotto for Italian street food (porchetta sandwich highly recommended) or the Americana cart for smash burgers, which the boys loved. “That was the best burger in my whole entire life,” Eli said. 

One shouldn’t overthink food selections. Practically everything is good. Because Bend is such a desirable place to live, service workers and restaurateurs are in abundance. Competition weeds out low performers. You’re not traveling to Central Oregon for bib gourmands, but you can expect food quality to be reliably high. And given our clientele (grade-school boys), this food scene was preferable. 

For a road trip crescendo, central Oregon is uniquely featured with thermal geologic activity that generates natural hot springs. If you want to be the family hero, take the kids to a natural spring in the wilderness. Terwilliger, Breitenbush, and Umpqua are day trips, but worth it. Plan ahead as conditions may inhibit access. We didn’t and had to settle for the Airbnb hot tub, which was also great. 

I was a little hesitant to return to the Pacific Northwest. I lived there before recommendation engines and algorithms had leached into culture. A time when — like a well guarded truffle-hunting location —  secrets still existed. Restaurants, trails, swimming holes, all passed along by word of mouth and out-of-print books. I didn’t really want to risk tarnishing my memories with exposure to the elements. 

Fortunately for us, and for you, plenty of underexplored territory remains. Further, when you’re traveling with kids, experiences that might seem mundane become magical when seen with fresh eyes.