Open-Air Oregon: A Rousing Road Trip through Nature and Culture

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.

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.

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.

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.

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.

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.

Enjoy breakfast at Wilson Ranches Retreat, then hit the road heading west toward Hillsboro. Venture just outside the town to continue your tour of Oregon’s natural wonders at Henry Hagg Lake. Here, placid waters and verdant shorelines make a prime location for stand-up paddleboarding. Rent a board from the lake house and meet up with your friendly instructor; paddleboarding lessons are offered on weekends. While you might be tempted to spend the entire day floating, make sure to carve out a little time to explore Hillsboro. The Five Oaks Museum and the Jackson Bottom Wetlands Preserve are both well worth a visit. See the colorful shops and art galleries along Main Street before making the hour-long drive to Portland International Airport to catch your flight home.