Road Trip: Oregon

Don’t worry about the band name, just rest assured there was an ample amount of jangly guitar playing and a fair amount of shoegazing onstage because I’m a ’90s kid at heart. I harbor not-so-secret hipster tendencies, so you probably never heard of them. Anyway, we all have our tastes, and it’s the venue I recall more than anything. I’ve been to a lot of underground bars and seen a lot of shows, but most of those don’t implant in the hippocampus like this.The Doug Fir Lounge (830 E. Burnside, Portland, 503-231-9663) is dim and unsubtly timbered as the name would imply with a certain je ne sais quoi that makes those tandem guitars reverberate a little stronger, especially with a local pint from Breakside Brewery (820 NE Dekum St., 503-719-6475) in hand.

Sea life exposed on rocks at low tide on the Oregon coast
Sea life exposed on rocks at low tide on the Oregon coast (Photo: Adobe Stock)

It’s easy to spend time indoors in Portland, Ore. Whether because of the overflowing well of indie music, the flood of craft libations or the artisanal food, which is never far away, it’s a place that encourages indulgence and mornings as foggy as the stereotypically overcast canopy. It’s also a staging ground for invigorating adventure under crystal-clear skies, where getting lost among the towering evergreens can shake off any kind of lingering haze. The push and pull never really subsides. Casual lingering over the last third of a pour over coffee gives way to an overwhelming urge to explore the trails, especially once the long gray of winter has mercifully given way to spring sun and the GORE-TEX becomes superfluous for a time.  

The hues of the Northwest are richer and the views, where the densest forest wanes and allows, are simply scaled differently. It’s time to chart your own trail west. Don’t sit still. There’s much to do.

Portland White Stag sign illuminated at night over Burnside Bridge. The sign can be spotted on top of Old Town's White Stag Building.
Portland White Stag sign (Photo by Justin Katigbak/Courtesy Travel Portland)


Portland has several notable nicknames. I suppose this is unsurprising for a place that was named via coin flip in 1845 when Francis Pettygrove of Portland, Maine defeated Asa Lovejoy of Boston two flips to one. It’s unclear if Pettygrove called heads or tails, but the penny used is on display at the Oregon Historical Society. The city’s official nickname, at least since 2003, is “City of Roses” owing to the area’s ideal climate for growing the flowers which can be admired at the International Rose Test Garden (400 SW Kingston Ave., Portland, 503-823-3636). The nickname I find most apt, however, is the one that was in vogue prior to the fateful coin flip. Stumptown.

The name was derived from the vast number of trees which were cut down to facilitate growth. Ever since European settlement shamefully and often violently displaced the native people of Oregon, including the Kathlamet, Wasco and Wishram, Clatsop and Clackamas nations, the area has been the epicenter of the lumber industry in the United States. Today it is the country’s top lumber producing state, and even the beloved professional soccer team is named the Timbers. But as much as the felled trees have shaped the area, the mountains rising from earth define the state’s identity.

Mount Hood, the iconic stratovolcano easily visible from Portland some 60 miles away, is so prominent as to have inspired debate about its height, with 19th century estimates pegging the mountain as the highest in North America at over 18,000 feet tall. Modern measurement reads 11,249 feet—oh, to live in a time where disinformation was wrought from lack of data instead of willful denial. Today Hood is the home of multiple ski resorts and is a hub of outdoor adventure. Take the trip from Stumptown to the hills and see for yourself.

Forest Park is a great place to escape the city and walk or hike more then 80 miles of trails
Hikers enjoy Portland’s urban playground at Forest Park (Photo by Justin Katigbak/Courtesy Travel Portland)


Emerging into the crisp morning air after a night at the Doug Fir Lounge is refreshing. Seeking some penance from my own decision making, I headed to the city’s northwest corner for a little outdoor therapy in Forest Park, a 5,000-acre respite from Portland’s energetic churn. Starting at Lower Macleay Park, I hiked through a dense temperate rainforest up the Lower Macleay Trail to the Wildwood Trail for roughly 2.5 miles. Along the way I passed a historic stone house covered in moss the forest was attempting to reclaim as I winded up the hillside before reaching the Pittock Mansion (3229 NW Pittock Dr., Portland, 503-823-3623).

Pittock Mansion, located in the West Hills of Portland
Visitors enjoy the sun outside of Pittock Mansion (Photo by Justin Katigbak / Courtesy Travel Portland)

The labyrinthine 46-room, French Renaissance-style chateau sits atop a hillside with an enormous vista overlooking Stumptown. On clear days Mount Hood is visible, as is the ominously flat-topped remnant of Mount St. Helens. Beckoned by the call of the colossal volcanoes, I descended back into the city before heading East to explore Oregon’s vast rivers and mountains.

I drove along the Columbia River, passing waterfalls and innumerable osprey nests until I reached Hood River. The first time I visited Hood River, someone earnestly asked me what water sport I did. Lacking any semblance of an answer has always bugged me, so I figured “when in Rome” and tried dusting off the remnants of windsurfing knowledge my father had imparted during my youth. I did mostly poorly, but the legendary winds were mercifully moderate so as not to thrash me too intensely. Lessons are available for those seeking more success than I was able to achieve.

The following day I departed Hood River to head to the high slopes of Mount Hood. Timberline Lodge Ski Area (27500 E. Timberline Rd., Government Camp, 503-272-3311) offers lift-served skiing most of the year and is open at least until the end of May. The Palmer Glacier sits high on Mount Hood’s south flank, offering expansive ski terrain and stunning views of the chain down volcanoes running along the country’s west coast. Remember, ski season never ends until you let it.

Food from Afuri Izakaya
Food from Afuri Izakaya (Photo courtesy Afuri Izakaya)


I could write several books about what to eat and drink in Oregon, but I’ll try to boil it down to a few essentials for you. We’ll start with coffee, and for that you’re going to want to head to The Clearing Café (2772 NW Thurman St., Portland, 503-841-6240). Simply put, it’s the best cup of coffee I’ve ever tasted in my life. There’s a reason it ended up in a Portlandia episode.

We can’t ignore the craft brewing culture either. The Cascade Brewing Barrel House (939 SE Belmont St., Portland, 503-265-8603) has an impressive selection of handcrafted, barrel-brewed sour beers. Typical beers these ain’t, and your palate will enjoy the one-of-a-kind flavors on tap.

Tuna melt at Double Mountain Brewery
Tuna melt at Double Mountain Brewery (Photo courtesy Double Mountain Brewery)

For incredible dining in PDX you won’t do better than Afuri Izakaya (923 SE 7th Ave., Portland, 971-386-2945). The wonderful Japanese small plates and free flowing drinks are a delight, especially the asari sakamushi, which features sake steamed clams, shoyu koji and house sourdough.

In Hood River, the best food and drinks come from the same establishment, Double Mountain Brewery (8 4th St., Hood River, 541-387-0042). The brick oven pizzas—try The Buffy with crumbled goat cheese, kalamatas and peppadew peppers—and the beer—the Vaporizer, a refreshing dry-hopped pilsner, is my all-time favorite—are salvation after a day on the water.

Hops at Double Mountain Brewery
Hops from Double Mountain Brewery (Photo courtesy Double Mountain Brewery)


McMenamins Kennedy School (5736 NE 33rd Ave., Portland, 503-249-3983) is one of several hotels associated with the McMenamins brewery in Portland. What makes this one stand out from the others is it’s actually located inside a former elementary schoolhouse. Some of the 57 rooms even have chalkboards on the walls. The on-site bar is an added bonus.

Hood River’s Columbia Gorge Hotel (4000 Westcliff Dr., Hood River, 541-386-5566) sits atop a cliff overlooking the truly stunning Columbia River Gorge. I assure you my words here don’t do the location justice. It’s the first place I ever spent an evening in Oregon, and I’ll never forget the view as the sun rose over the gorge the next morning.

On Mount Hood, no place can compare to the Timberline Lodge (27500 E. Timberline Rd., Government Camp, 503-272-3311). The enormous building, which is just steps from the chairlift, was constructed during the 1930s by the Works Progress Administration during the Great Depression. The iconic hotel was used for the exterior shots in The Shining though as far as I know there’s nothing to fear in room 237.

Couple fat biking in Pacific City
Fat biking in Pacific City (Photo by Dylan Van Weelden/Courtesy Travel Oregon)
Hiker overlooks Crater Lake National Park
Crater Lake National Park (Photo by Satoshi Eto/Courtesy Travel Oregon)


Start: Pacific City // End: Painted Hills

From the misty coast to a temperate rainforest to arid high-desert hills, Oregon’s landscape is one of the dramatically varied natural wonders. Choosing just seven among them is a harrowing task, but one that allows the adventurous to sample the diversity on tap.

1 / Surf the Oregon Coast

Paddle out for uncrowded waves at beautiful Pacific City. The weather is sometimes moody, but the peelers are perfect. Stop into Pelican Brewing Company after trading the wet suit for board shorts. 

2 / Hike to Waterfalls in the Columbia River Gorge

The 620-foot-tall Multnomah Falls is the tallest of 77 stunning waterfalls on the Oregon side of the Columbia River Gorge. A moderate hike gets you to the top, and the postcard-perfect Benson Bridge is worth a shot for the ’gram.

3 / Go Mountain Biking at Mt. Hood

Take a rip down the famous Timberline to Town Trail, where more than five miles of singletrack wind down the mountain from Timberline resort to the town of Government Camp. Gravity lovers can lap the lifts at Timberline Bike Park.

4 / Take a Boat Tour of Crater Lake

Experience the iconic geology of Crater Lake with a boat tour from Crater Lake Hospitality. The one-mile Cleetwood Cove Trail to the water’s edge is beautiful enough, and the three-hour stop on Wizard Island gives you the chance to explore the unique area rarely seen up close.

5 / Try Rock Climbing at Smith Rock

The towering, volcanic ash spires of Smith Rock attract climbers from around the world. Smith Rock has thousands of routes to test every level of climber, and newbies can get a proper introduction with Smith Rock Climbing Guides

6 / Visit Hells Canyon Overlook in the Wallowas

With more than 8,000 feet of drop to the Snake River, Hells Canyon is the country’s deepest, dwarfing even the Grand Canyon for scale. An abundance of whitewater recreation awaits for those who’d prefer the view from rapids the on the river from the depth’s of this massive, deep canyon.

7 / Get Lost in the Painted Hills

The Martian-like vibes of eastern Oregon’s painted hills—punctuated with arid red hues—feel worlds away from the state’s soggy stereotype. John Day Fossil Beds National Monument is the gateway to exploring the surreal landscape.  

Astoria-Megler Bridge in Astoria, Ore.
Astoria-Megler Bridge in Astoria (Photo by Joni Kabana/Courtesy Travel Oregon)
Oregon Dunes
Oregon Dunes (Photo courtesy Travel Oregon)


Start: Astoria // End: Oregon Dunes National Recreation Area

History, stunning vistas and diverse recreation converge along Oregon’s coastline. Feel the refreshing sea breeze, explore the iconic, rocky shore and enjoy charming coastal towns.

1 / Historic Astoria

Start with a visit to the Columbia River Maritime Museum for a rundown on the Northwest’s rich seagoing history before stopping at Fort Clatsop, where a full-size recreation of Lewis and Clark’s fort lets you walk in the footsteps of America’s most famous explorers.

2 / Seaside Promenade

Visit Oregon’s first beach resort town at Seaside. Step back in time with old-fashioned family attractions including an arcade and carousel before enjoying the paved, oceanfront promenade.  

3 / Three Capes Scenic Loop

Take a side trip between Tillamook and Pacific City to enjoy three capes. Cape Meares has panoramic views and a historic lighthouse, Cape Lookout has pristine beach access and Cape Kiwanda has tide pools alongside enormous sand dunes and seaside cliffs.

4 / Tillamook Bay Heritage Route

Connecting five communities around Tillamook Bay—Barview, Garibaldi, Bay City, Tillamook and Cape Meares—the Heritage Route offers access to unspoiled natural beauty like the forested trails at Kilchis Point Reserve as well as local culture with indulgent stops along the North Coast Food Trail.

5 / Yaquina Head Outstanding Natural Area

Outstanding is in the name! While the picturesque eponymous lighthouse is a gorgeous sight, it pales in comparison to the marine life including flocking sea birds and migrating gray whales you’ll see here.

6 / Cape Perpetua Scenic Area

Trails through the seaside rainforest and rocky coastline make the ideal coastal hiking setting. Attractions like the Spouting Horn, Devils Churn and Thor’s Well keep motivation high as the miles stack up.

7 / Oregon Dunnes National Recreation Area

For 40 miles between Florence and North Bend, enormous sand dunes dominate the coast. From day hikes at the Jessie M. Honeyman Memorial State Park to dune buggy tours in Florence, there are myriad ways to adventure.

Couple in canoe on Sparks Lake under Broken Top Mountain
Sparks Lake below Broken Top Mountain (Photo: Adobe Stock)
Food and cocktail from Wild Rose Northern Thai Eats
Wild Rose Northern Thai Eats (Photo courtesy Wild Rose Northern Thai Eats)
Thor's Well on the Oregon coast
Thor’s Well on the Oregon coast (Photo: Adobe Stock)


Start: Bend // End: Three Sisters Wilderness

Alpine lakes scattered along the Central Oregon high country are the perfect targets for outdoor adventure. Backdropped by volcanic strata and the Cascade Range from Bend to the Three Sisters Wilderness, the Cascade Lakes Scenic Byway is a can’t-miss route.

1 / Begin in Bend

The sunny city at the heart of central Oregon is the gateway to Cascade Lakes adventure, but it has plenty of its own shine. Get some grub at Wild Rose Northern Thai Eats and some suds from local brewery 10 Barrel before you hit the road.

2 / Century Drive to Mt. Bachelor

The road climbs from Bend towards Mt. Bachelor along the Deschutes River, with fishing and canoeing access, past lava flows and ponderosa pine forest before reaching the enormous volcano. Play along the way or head straight to Bachelor—it’s home to famed biking and hiking trails—which can be enjoyed adrenaline-free by riding the lift for a sunset dinner at Pine Marten Lodge.

3 / Hike Broken Top Mountain

Leaving Bachelor, the road passes by Broken Top Mountain, an impressive stratovolcano. Lava dams and glacial ice have formed dozens of lakes in the area, some of which you’ll pass by along the Broken Top Trail.

4 / Land of Lakes

An expansive wetland sits on the edge of Sparks Lake, a scenic 250-acre body of water. A short loop hike explores the jagged lava shore, a perfect encapsulation of the violent geologic activity that shaped the area. Nearby Devil’s Lake is a glowing emerald green waterway surrounded by evergreen trees.

5 / Three Sisters Wilderness

The Pacific Crest Trail (PCT) extends into the Three Sister Wilderness, a nearly 300,000-acre area highlighted by the Middle, North and South Sisters, all volcanic peaks reaching over 10,000 feet. Hike a section of the PCT, made famous by the 2014 film Wild or go fly fishing on the Deschutes River for the fabled lunker “Cranebow” rainbow trout.

Family whitewater rafting in Indigo Creek Outfitters
Indigo Creek Outfitters (Photo courtesy Indigo Creek Outfitters)


Start: Phoenix // End: Jacksonville

Oregon’s wine culture is well-known, but wine tasting adventures needn’t be quiet, sit and sip affairs. Libations and adventure flow together in the Northwest.

1 / Whitewater and Wine on the Rogue

Let the good times flow with a morning on the water followed by an afternoon of wine tasting. Indigo Creek Outfitters starts the morning with a Rogue Valley Rapid Run before an afternoon of being toted around in the Bravo Outings wine tasting vehicle to a variety of local wineries.

2 / Grapes and Safari in the Umpqua Valley

Stop in at Abacela Vineyards—famous for their Tempranillo varieties—before heading to the neighboring Wildlife Safari, the only drive-through animal park in Oregon. Abacela provides hay to Wildlife Safari for their exotic wildlife, including rhinos, giraffes, zebras and lions, and receives nutrient-rich “zoo-doo” to use as fertilizer at the winery.

3 / Wildflowers, Wine, and Pizza

Start the day with a hike at Table Rocks, where wildflowers like the extremely rare dwarf wooly meadowfoam grow. The moderately easy hike rewards with stunning views. Finish the day at Kriselle Cellars where the wood-fired pizza pairs well with the cabernet sauvignon.

4 / Trestles and Test Tubes

Red Lily Vineyards serves up quirky fun with wine tastings out of test tubes in a beautiful setting along the Applegate River. The ports aren’t to be missed. Afterward, stop by the historic Mckee Bridge, a car-free, covered span built in 1917 to connect the town of Jacksonville to a nearby copper mine. It’s a wonderful spot to take a dip if the weather is right. 

For more travel ideas, visit Read more about our Road Trip Series here.

Tony Gill
Tony Gill
Tony Gill is the outdoor and Park City editor for Salt Lake Magazine and previously toiled as editor-in-chief of Telemark Skier Magazine. Most of his time ignoring emails is spent aboard an under-geared single-speed on the trails above his home.

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