Many visitors to Portland, Oregon extend their trips in order to take advantage of the Willamette Wine Country, the idyllic valley where the roads are practically paved with pinots, both noir and gris. With wine-producing towns such as Newberg and Dundee located about 20 minutes from the city, the majority of travelers tend to stick to the northern part of the region. But there’s much more beyond the northern valley. A mere hour or two of driving south reveals the charms of the less-trodden parts, with a host of working farms, quaint towns, outdoorsy diversions and, of course, excellent winery stops. Wondering how to do it? We created an itinerary for you.

The trip: Four Days, 350 miles, starting from Portland International Airport (PDX), traveling south through the valley west of the Willamette River, before looping south of Eugene and returning north to the city, this time east of the river.

How to do it: Car rental is the way to go. Avis, Hertz, National, Dollar and Enterprise all have on-site rentals at the airport.

When to go: It depends what you want. The blossoms of springtime provide breathtaking scenery, especially for hikers, while June through September offers the warmest weather and least rainfall. True oenophiles opt for harvest season, during September and October, and wine auctions in November. “Cellar season” in the winter allows for less-crowded tasting rooms.

Day 1: Independence, Oregon

As you leave Portland proper, hulking city structures and strip malls soon yield to fir-lined byways and open green pastures surrounding sturdy farmhouses. You’ll know you’ve arrived in the Willamette Valley when vineyards stretch as far as the eye can see—there are 765 of them, supplying 564 wineries. Along the way, visit Martha’s Tacos in Lafayette, a little over an hour into the drive, which is known for its crispy tripe tacos, bulging pork burritos, and “wet” tamales, drenched in red sauce. After a bite, continue south for 32 miles and stop in the riverside town of Independence, where pioneers from eponymous Independence, Missouri, came by wagon to settle in 1845. The Independence Hotel makes for a great modern-day settlement, right on the banks of the Willamette River. Opened in fall 2019, the terracotta and sand-colored structure and the newly refurbished Riverwalk path alongside it signal boom times in the town, due to its commutable convenience to the state capital of Salem and a reputation as a hotspot for agricultural tech. Some of the 75 rooms feature terraces with river views. The hotel’s roof deck, however, offers an even more expansive view, along with a firepit.

a large room

© Courtesy The Independence Hotel

The Willamette Valley Scenic Bikeway lays just over the River Road bridge and is a great place to put two wheels to use. Start there for a beautiful 25-mile loop through farmland and a nature refuge before crossing back via the Buena Vista Ferry. Since Independence was once known as the “hop capital of the world,” a stop at Rogue Hopyard Farms is warranted. The tasting room serves beer brewed with ingredients cultivated on site, such as honey and jalapeños. There’s also pub food, roving farm animals, and outdoor games for entertainment.

Spend the late afternoon and early evening exploring Downtown Independence, compact enough to do on foot. The Independence Amphitheater—a popular spot for dogwalking when not hosting outdoor movies, concerts, and a farmers market—lies across the street from the hotel. On the corner of Main Street, the laptop crowd fills wifi-hub Brew Coffee and Tap House. The Cooper Building across the way is Independence’s visual icon. Built in 1895, the Queen Anne style building houses a candy store, an ice cream shop, and a group of homegrown retailers. A few blocks further into town, nostalgic shoppers will hit the jackpot at Picken Chicken Antiques, Second Chance Books, and Same As it Never Was Vintage. The Jubilee Champagne and Desserts Bar is a fun stop while you admire your purchases.

Day 2: Corvallis

Rise and shine and take advantage of breakfast at the hotel (included in the room rate) before hitting the road. Among the offerings: fresh, soul-hugging biscuits and gravy, fluffy scrambled eggs, and locally made sausage. The staff is especially proud of the homemade marionberry jam, with good reason. Corvallis, 22 miles to the south and home of Oregon State University, is the next stop. A great way to explore downtown: the Alley Art Walk, a self-guided tour highlighting public art along Madison Avenue. Charming boutiques, such as a chocolatier and a book shop, also dot the trail. The walk culminates at the Riverfront Commemorative Park, an urban green that also features its share of sculpture. Stop for lunch at Bellhop, located in the building that was once the historic Hotel Corvallis. John F. Kennedy slept here while on his Presidential campaign trail in 1960. The fried chicken is the talk of the town, but the meatloaf, served with sausage gravy and mashed potatoes, is righteously tagged “of the gods.”

a group of people sitting on a bench in a garden: Students on campus Oregon State University in Corvallis Oregon

© Alamy
Students on campus Oregon State University in Corvallis Oregon

From there, it’s another 25 miles south through fields and twisting mountain roads to Leaping Lamb Farm. Originally homesteaded in 1862, today the farmhouse and cottage serve as a farm stay where guests can gather eggs, feed the animals, work the vegetable garden, or just enjoy the bucolic setting. Hiking trails spread throughout the site; keep an eye out for “fairy houses” built within some of the towering trees. The land is also home to turkeys, lambs, goats, chickens, horses, a peacock, friendly dogs, barn cats, and a somewhat rotund, affectionate donkey named Paco. Tours are available for day-trippers but it’s a worthy night’s stay (from $175). Barbecue grills and a kitchen are available for DIY meals; or nearby Deb’s Café offers up comforting specialties like clam chowder and prime rib.

Day 3: Wineries

As hard as it is to leave the pastoral charms of Leaping Lamb behind, more natural beauty lies ahead at the Alsea Falls Recreational Site, about 12 miles south. There, take a gander at the rushing 30-foot falls before hiking to Green Peak to admire an even more impressive 45-footer.

a group of people in a field

© Courtesy King’s Estate Winery

Once you have your nature fix, it’s wine time. Drive 50 miles south to the aptly named King’s Estate Winery, where 1,000 sprawling acres of vineyards produce some of the region’s best biodynamic grapes. Pinot gris is their prized grape; their wine portfolio also includes pinot noir, chardonnay, viognier, sauvignon blanc, gewürztraminer, cabernet, syrah, Riesling, muscat, and even cider fresh from the property’s apple and pear orchards. Try a flight at the beautiful cherrywood bar in the tasting room. Until the restaurant and tasting room can safely reopen from pandemic, the winery can accommodate a limited number of picnickers who may wish to bring their own provisions, buy a bottle of wine from the Tasting Room, and find a nice, secluded spot to spread a blanket and enjoy a front-seat view of the landscape.

After some sustenance, drive about 20 miles to Eugene, Oregon’s second largest city, and check in to the bespoke boutique hotel Inn at The 5th, where you’ll be greeted with a glass of wine upon arrival. Each room contains a private butler pantry for room service, which should not be missed as it comes from the James Beard Award-nominated Marché restaurant.

Day 4: Eugene

Inn at The 5th is conveniently located adjacent to the 5th Street Public Market, so why not spend the morning browsing the shops? Start with breakfast at Provisions—perhaps their signature breakfast pizza with bacon, potatoes, eggs, mozzarella, and grana Padano—before checking out the wares at shops like Made in Oregon, purveyors of local products; New Twist housewares and jewelry; and Pendleton Woolen Mills, makers of cozy wool blankets famous the world over.

a view of a city next to a body of water: View of Eugene Oregon and Willamette River

© Diane Bentley Raymond/Getty
View of Eugene Oregon and Willamette River

Then head downtown for a dose of Eugene’s famed counterculture. Pay respects to Merry Prankster (and former Eugene resident) Ken Kesey at the statue in Kesey Square, and if it’s Saturday, take a trip to the Saturday Market for artisan crafts and live music. For lunch, stop at Party Downtown Bar, where the flavorful fried chicken sliders are as mind-blowing as a tab of LSD (allegedly). A stroll along West Broadway after lunch will reveal a row of interesting spots to pop in, such as Lazar’s Bazar, an emporium full of head-shop items, posters, and rock and roll memorabilia.

Before leaving Eugene and heading two hours north back to PDX, consider a stop at the Cascades Raptor Center, home to 40 birds of prey, from bald eagles to vultures. In addition to the resident raptors, the center has rehabilitated more than 2,000 injured birds and released them back into the wild. There are fewer more rewarding and inspirational ways to bid the region farewell before taking flight, yourself.