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  • A peaceful day paddling the Clackamas River near Estacada, Oregon
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    River Views and Artisan Brews in Estacada

  • Surfers enjoy the waves at Agate Beach in Newport, Oregon
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    Newport: An Oceanfront Gem

  • Fly fishing on the McKenzie River near Eugene, Oregon
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    River Outings for All in Eugene

  • Touring the vineyards at Padigan Wines in Medford, Oregon
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    Sip Your Way Through Medford

  • Taking in views of lava flows at the Newberry National Volcanic Monument near La Pine, Oregon
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    La Pine: Rugged Journeys and Unbelievable Landscapes

  • Riding horses on the expansive grounds of Wilson Ranches Retreat in Fossil, Oregon
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    Learn the Way of the Cowhand in Fossil

  • Stand-up paddleboarding on Henry Hagg Lake in Hillsboro, Oregon
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    Hillsboro: Lake Charms Meet Cultural Gems

Paddling Henry Hagg Lake in Hillsboro, Oregon
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Open-Air Oregon: A Rousing Road Trip through Nature and Culture

By Keely Parker

  • Route distance:
    1,450 km
  • Suggested Time:
    1-2 weeks

Take an unforgettable tour of Oregon, where incredible scenery, adventurous outings and friendly communities are waiting to welcome you.

Embark on kayaking, fishing and even surfing excursions, all set against the majestic backdrop of Oregon’s outdoor wonders. Along the way, stop to sample craft libations and enjoy quaint accommodations in welcoming mountain towns with historic charm. Hop aboard a flight to Portland International Airport and get ready to discover why Oregon is a dream destination for nature lovers.

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A peaceful day paddling the Clackamas River near Estacada, Oregon
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River Views and Artisan Brews in Estacada

The scenic riverfront town of Estacada, just a 45-minute drive south of Portland International Airport, provides an excellent homebase for those looking for outdoor activities on land and water. Spend the morning paddling the Clackamas River, where untouched beauty and tree-lined estuaries are sure to ignite your spirit of adventure. Admire views of the Cascade Mountains and Mt. Hood National Forest from the peace of your kayak. After a morning on the water, head into town to grab a bite and meet the locals. Sip on a curated selection of Oregon-brewed beers and chow down on wood-fired pizza at Clackamas River Growlers, where you may pick up a new language. Owners Linnea and Mark, along with many of the taproom’s bartenders, are deaf: They’ll teach you how to order your brew of choice in American Sign Language.

225 km
2.75 hours by car
02
Surfers enjoy the waves at Agate Beach in Newport, Oregon
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Newport: An Oceanfront Gem

Head southeast to Oregon’s central coast, where you’ll find the lively town of Newport. Get to know this laid-back seaside community by taking private surfing lessons at Agate Beach. Head to Ossies Surf Shop to pick up your gear and get ready to hit the water. Whether you’re a newcomer or a seasoned surfer, knowledgeable instructors will help you take your skills to the next level. Be sure to spend a little time watching the native wildlife, like sea lions and several species of shorebirds. When hunger strikes, check out Newport’s food trucks for tasty fare. You’ll find everything from Hawaiian-inspired small plates to coastal classics like fish tacos and fish and chips.

154 km
1.75 hour by car
03
Fly fishing on the McKenzie River near Eugene, Oregon
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River Outings for All in Eugene

It’s a little less than a two-hour drive southeast to Eugene, where natural wonders meet artsy vibes. Set your sights on the McKenzie River National Recreation Trail, a premier spot for hiking, trail running, camping and more. Thrill-seekers will delight in whitewater rafting excursions on the river, while those looking to take it easy will enjoy the relaxed pace of a fly-fishing tour. No matter how you choose to explore, you’ll be surrounded by the majesty of the Cascade Mountains. Be sure to spend some time wandering Eugene’s colorful downtown to see magnificent murals, savor locally roasted coffee and enjoy spectacular theater shows.

270 km
2.75 hours by car
04
Touring the vineyards at Padigan Wines in Medford, Oregon
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Sip Your Way Through Medford

Make your way south to Medford, located in the heart of the sunny Rogue Valley. This Southern Oregon region boasts an American Viticultural Area designation, and the wines produced here are among the most well-regarded in the USA. Get a taste of the local bounty on guided wine tours, where you’ll be chauffeured to several area wineries for tastings and educational programs. Explore the expansive vineyards of Hummingbird Estate, enjoy a game of Bocce ball at Padigan Wines and savor artisan cheeses and panoramic views at Kriselle Cellars.

143 km
2.75 hours by car
05
Taking in views of lava flows at the Newberry National Volcanic Monument near La Pine, Oregon
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La Pine: Rugged Journeys and Unbelievable Landscapes

Drive north from Medford to reach La Pine, where nature is the main attraction. Adventure through geological marvels on a high-adrenaline ATV tour: Guided excursions take you to the heart of the Deschutes National Forest where you’ll traverse the otherworldly terrain of the Newberry National Volcanic Monument. Ride through ancient lava flows, enjoying supreme views of one of the USA’s most distinctive landscapes. After, head into town to shop for artisan crafted goods at the Made in La Pine Store, then settle down for the night in the rustic comfort of a local lodge or camping site.

250 km
2.75 hours by car
06
Riding horses on the expansive grounds of Wilson Ranches Retreat in Fossil, Oregon
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Learn the Way of the Cowhand in Fossil

From La Pine, travel north to the town of Fossil to immerse yourself in authentic Western ambience. At Wilson Ranches Retreat, you can try your hand at outdoorsy activities like horseback riding and hiking. If you’re new to the cowboy lifestyle, experienced ranchers will help you get comfortable in the saddle with riding lessons and guided ranch rides. After a day riding the range, you won’t even have to leave the ranch to kick back in comfort: Spend the night in a cozy private room at the onsite bed-and-breakfast inn.

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