Oregon’s best places to live when you can work remotely from anywhere
written by Cathy Carroll
Reflect a moment on how you felt during a favorite Oregon getaway—gliding through fresh powder, hiking among fragrant pines, swimming in a lake reflecting a snow capped peak, paddling on liquid serenity or being rejuvenated by the salt-infused breeze of the Pacific. Remember wishing you didn’t have to leave, vacation over, back to work?
More than ever, work can be wherever you choose. To be certain, the global pandemic has few silver linings, but the shutdown of offices and the rise of remote work allows more choice in where to live. Across America, millions have begun working remotely since last spring, a trend that’s clearly taking hold in Oregon, too. “Zoom Towns,” idyllic places where you can connect with workplaces virtually, have spurred migrations that appear to be doubling down on existing growth patterns, although it’s too soon to measure, according to the state Office of Economic Analysis.
In general, vacation areas across the U.S. have seen a jump in interest, according to Zillow, the online real estate marketplace. Another Zillow study found that the freedom to work remotely could prompt nearly 2 million renters to look for homes elsewhere. They can’t comfortably afford to buy homes in their current metro areas, but could afford a typical U.S. starter home valued at $131,740. That demographic included 43,191 renters in Portland, 11.7 percent of that group.
You’ve seen those virtual backgrounds for Zoom, the ones that make it look as if you’re on a beach at sunset, the chairlift on bluebird day, or an impossibly still lake. Maybe you’re using one right now, attending a company meeting from a spare bedroom. Why not hit the delete button on the fake scenery and go for the real thing instead?
Ready? We picked five of the best places where you can take your remote work to new heights and live your best life.
Some of America’s best theater, food and outdoor pursuits can now be a part of your everyday life, not just a special treat in this small city at the foot of the Siskiyou and Cascade ranges. Whether it’s before you log in to work, on a lunch break or as soon as you shut down your laptop, you can hit fifty miles of scenic alpine trails for a run or mountain bike ride right from your paved city street.
Mt. Ashland Ski Area, about a thirty-minute drive from downtown, offers forty-four runs. Being close will let you perfect your skills for skiing the chutes of the “Bowl.” Nordic ski or snowshoe to vistas over the Rogue Valley and Rogue River-Siskiyou National Forest and to Mt. Shasta in California.
In summer, take a day hike on the Pacific Crest Trail, within a hundred yards of the Mt. Ashland summit. One of the world’s most biodiverse temperate forests, the PCT is home to 3,500 wildlife species and 125 of the 160 butterfly species in Oregon.
Diversity doesn’t end in the wilderness. The arts are part of Ashland’s DNA. America’s oldest Elizabethan theatre, the Oregon Shakespeare Festival and Southern Oregon University translates to a stimulating community of artists, galleries, museums, independent films and live music. Even when indoor venues are closed during the pandemic, a range of alternatives fill that gap, including outdoor public art installations, a fun, hip downtown and OSF’s new digital storytelling, classes and conversations on everything from the classics to LGBTQ art.
It all adds up to living and working in a place where you can log off and tune in to a healthy lifestyle with an open-minded, stimulating culture. Alexandra Sascha Meier, a former corporate executive who’d traveled abroad extensively, said she moved to Ashland several years ago and loves the groundedness of working from home as a self-employed professional coach. “In Ashland, I can work with people from all over the globe, live a simple, less cluttered existence,” she said after wrapping up an afternoon of cross-country skiing. “It is a place where people care how things are going—intellectually, professionally, emotionally. You can practice stillness here in the midst of the fast-paced, dynamic world.”
Robynne Whitaker, a local real estate broker, said that since the late ’90s, Ashland has been attracting people who work remotely full-time or telecommute part-time. Although home inventory is a third of what it was last year, sales jumped nearly 50 percent in October compared to October 2019, she said.
Jump into that hypnotizing screensaver of the monolithic rock rising from the ocean, backlit by the setting sun. How? Take a selfie with Cannon Beach’s iconic Haystack Rock and make it your background on your morning Zoom meeting. First, though, let the salty, Pacific air clear your mind.
Get your toes in the sand. Pound out a couple of miles at a vigorous pace or wade through tide pools hosting starfish, Seussian-green anemones and comically skittering crabs. Clarity gained, you’ll check off a surprising number of tasks before midday. Back away from the keyboard to stretch and connect with locals at Cannon Beach Yoga Arts (or via live stream until classes reboot in the studio or on the sand).
For that afternoon call, take it from Ecola State Park, as you walk through old growth rainforest. When you’re ending the call, reward your productivity by taking in the headlands, bald eagles riding the thermals and the Tillamook Rock Lighthouse standing sentinel over your home shore.
Manage your work calendar around the tides. Go fishing, clamming and crabbing. Opt for full immersion and learn to surf. Northwest Women’s Surf Camps incorporates beach yoga in its programs, and has private or co-ed group lessons for adults, teens or parents and kids, starting in spring.
The camps’ director, Lexie Hallahan, who has lived in the area for thirty-five years, said the beauty of the ocean along with the pubs, bistros and shops creates a strong community. “People really care for one another,” she said.
You’ll sense that after a well-rounded day and you connect with others, whether it’s Hallahan’s 93-year-old neighbor sipping hot cocoa and watching the breakers from his car, or fellow surfers recharging with a locally brewed Updrift IPA from Pelican Brewing Company.
By now it’s time to pair the frothy ale with the pub’s Oregon beef burger and a dollop of Kiwanda cream ale aioli. For a culinary connection to the sea, pick up cod, halibut or salmon fish and chips from Ecola Seafood.
Should work summon you from your coastal dream, you can be at the Portland Airport in about ninety minutes.
Megan Davis has seen nearly every member of her family migrate to Hood River since she moved there twenty-three years ago. Her youngest sister was one of the last holdouts, until last spring. After her office was closed because of the pandemic, the single 30-something in Portland was working from home instead of commuting downtown.
“She said, ‘Now all I do is stand in front of a computer—I can do that anywhere,’” said Davis. Hood River is a powerful draw on its own, regardless of being near family. “In forty-five minutes, you can be on a chairlift (at Mt. Hood Meadows Ski Resort), at Teacup Lake Nordic skiing or in the backcountry, or get on five different rivers if you’re a paddler,” she said.
You can run out of breath (despite all the outdoor aerobics) in naming ways to play. You absolutely must include windsurfing and kiteboarding in the Columbia River Gorge. If it seems like a steep learning curve, people at area shops such as Big Winds, Brian’s Windsurfing and Windance can help flatten that curve. Throw in whitewater rafting, kayaking, standup paddling and fishing, too.
Bike or drive the Fruit Loop—a 35-mile ring punctuated by farm stands offering some of America’s best pears, apples, peaches, nectarines and berries. Or consume them another way, at wineries, cideries, breweries and restaurants in the valley or the city’s charming downtown.
“In forty-five minutes, you can be on a chairlift, at Teacup Lake Nordic skiing or in the backcountry, or get on five different rivers if you’re a paddler.”
— Megan Davis, Hood River Resident
Working remotely here isn’t apt to let you feel isolated, because the sense of community is strong. Volunteerism at the local food bank and other nonprofits thrive and a local church found innovative ways to help the homeless, Davis said, calling her town “generous, accepting … open-minded.”
This place, although bordered by Oregon’s tallest mountain and most famous river, isn’t remote. “It’s close enough to get to a city (Portland) and that’s one of the reasons I love being here,” Davis said. “I can get on a plane in sixty minutes and go anywhere.”
In some ways, this is the epitome of a remote work town, far from any city life, in a place of deep, pure beauty. In any Zoom session here, be sure to have on your hiking gear, so that as soon as it’s over, you can roam around in your backyard.
Your backyard being Oregon’s largest wilderness area, the Eagle Cap, 556 square miles guarded by the 9,000-foot granite peaks of the Wallowas. The federally protected land is virtually unchanged since Chief Joseph’s Nez Perce summered and gathered huckleberries here.
It’s the kind of place that doesn’t let anything on a screen be taken all too seriously. To gain that perspective, hit the nearby trails from Wallowa Lake. Walk through an alpine forest with mountain goats, mule deer and elk to BC Falls.
These landscapes keep you humble. Buckhorn Lookout is Oregon’s answer to the Grand Canyon. Move on to Oregon’s largest natural intact grassland, the Zumwalt Prairie, where the elk herds roam. Let 515 square miles of wildflowers and grasses swaying in the breeze erase any vestige of any memory of any cubicle. Head to Hells Canyon National Recreation Area, the deepest river gorge in North America for motorcycle touring, world-class whitewater boating and mind-blowing vistas.
Back in town, artists, cowboys, ranchers and craftspeople create a social fabric weaving the traditional and progressive. Literary arts are the focus during the Summer Fishtrap Gathering every July, devoted to good writing, challenging conversations and the American West. The week-long conference has hosted authors such as Bill Kittredge, Ursula K. LeGuin and Cheryl Strayed.
Unplug daily by heading into town, where deer nonchalantly stroll the streets dotted with art galleries, handmade chocolate shops, eateries and boutiques.
It’s not unusual to arrive at someone’s home here to find them sweating, in trail running or Nordic skiing gear, having bolted back from an outing to hop on a business call. For years people have found ways to bring their work with them to their favorite outdoors playground.
The beauty is not only in the volcanic landscape, rugged high desert surroundings and the clear, melted-snow Deschutes River that runs through it. It’s also the priority that the community places on getting out there to play in it.
The Deschutes National Forest rolls out its green welcome mat, offering up hundreds of miles of trails for mountain biking, skiing, hiking, fishing, rafting, kayaking, swimming and standup paddling. For more arid conditions, head east of town to the Oregon Badlands Wilderness, where the terrain is punctuated with ancient, twisted junipers and rocks that appear to be hefty but are featherweight, dried lava.
If your organization has a competition for best Zoom background, you could nail it by taking a meeting from atop a volcano, Pilot Butte, right in the city limits. Easy access to it all this lets you press the power-on button for your soul before you touch anything work related. Powering down afterward is easier, too.
Take to the paths through the Old Mill District, past the Les Schwab Amphitheater, which draws national acts, and along the Deschutes River to Drake Park downtown. Unwind at a brewery, trending restaurant or food cart, browse the boutiques and catch live music or theater.
The blue skies and sun have long seemed to influence the culture. People smile and wave readily and put “Be nice, you’re in Bend” stickers on their cars. They take the attitude elsewhere, too, which is easily done from Redmond Municipal Airport, about a 30-minute drive from town.