Loading LoadingDay 1: Fresh Fare, Cold Beer Awaits in the Willamette Valley (Portland to Oregon City)
Fly into Portland International Airport (PDX), and drive just 30 minutes south to your basecamp at the Best Western Plus Rivershore Hotel in neighboring Oregon City. Conveniently located along Interstate 205, all rooms offer views of the Willamette River and easy access to downtown Oregon City—winner of the 2018 Great American Main Street Award. Grab lunch at Wayward Sandwiches in the nearby community of Canby; the deli sources its ingredients locally, often from farmers in the area, and boasts a curated selection of hard-to-find local wines and international varietals.
After lunch, get artsy as you cross the Willamette River, head to Lake Oswego, and take the city’s free Gallery Without Walls walking tour—where you’ll see up to 80 works of art in outdoor spaces around the community. After your walk, savor a well-deserved beer on the lakefront patio at Stickmen Brewing Company—or enjoy a glass of wine at Domaine Serene Wine Lounge near Millennium Plaza Park.
From there, head to The Kitchen at Middleground Farms for your pre-reserved cooking class with chef Jessica Hansen and her stellar staff. Set on a working farm, The Kitchen’s fully modern commercial space offers classes where even experienced foodies are bound to learn something new.
Day 2: Head Into the Heart of Oregon Wine Country (Oregon City to Dayton)
Start your day with brunch at The Hive Social, known for crafting made-from-scratch dishes with locally sourced ingredients. From Oregon City, embark on an hour-long drive west to Wine Enthusiast magazine’s 2016 Wine Region of the Year. As you enter the heart of Oregon Wine Country, you’ll find more than 700 wineries, from boutique artisans to popular estates. Pair your tastings with a stop at one of the area's many U-Pick farms, depending on the season, to grab your choice of blueberries, apples, peaches, and more; the Willamette Valley produces more than 170 crops each year, many of which show up on dinner plates and in wine glasses at destinations you'll visit this weekend.
Stop at Tabula Rasa Farms at The Ground to learn more about regenerative farming and permaculture in the Willamette Valley via bookable farm tours. (Later on, you can see the farm’s work in practice at the McMinnville-based restaurant, Humble Spirit, which uses Tabula Rasa’s meats in a variety of dishes.) Following your farm tour, visit the beautiful tasting room at nearby Fairsing Vineyard to try Pinot Noir, Chardonnay, and Rosè. Next, stop by Soter Vineyards at Mineral Springs Ranch—which hosts a biodynamic farm, vineyard, and tasting room. (Pro tip: Book a Provisions Tasting experience that pairs Soter’s acclaimed wines with a guided culinary experience that showcases ingredients grown on-site.)
After a full day of exploring and sipping, treat yourself to dinner at Rosmarino Osteria in Newberg for traditional Italian fare—or Ruddick/Wood for dishes that are sourced from and inspired by the seasonal bounty of the Willamette Valley.
If you’re looking for a quirky glamping experience, spend the night at The Vintages Trailer Resort just outside the community of Dayton; The Vintages host renovated and updated Airstream trailers in the heart of Oregon Wine Country. For more luxury, spend the night at The Allison Inn and Spa in Newberg.
Day 3: Kick Back on Country Byways and in Quirky Eugene (Dayton to Eugene)
Start your morning with breakfast at Alchemist's Jam in McMinnville; the hip spot serves some of the area’s best breads, cinnamon rolls, biscuits, and other pastries. Continue your southbound trip with a stop at Left Coast Estate, a family-owned-and-operated winery specializing in sustainable viticulture and winemaking; if you’re hungry for lunch, Left Coast Estate also serves an appetizing selection of wood-fired pizzas. For more of the Willamette Valley’s acclaimed wines, pop over to Johan Vineyards next door for beautiful views and certified biodynamic wine.
Continue your day’s trip south on Highway 99E and Territorial Highway (one of Oregon’s oldest roads). This heads through one of Oregon’s newest federally designated American Viticultural Areas (AVA)—the Lower Long Tom AVA; visit Benton-Lane Winery, whose vines straddle two counties. Enjoy a glass of Pinot Noir on the tasting room’s sun-dappled patio that looks over the Southern Willamette Valley; on a clear day, views offer a glimpse of the snow-capped Mt Jefferson. Afterward, hop over to Brigadoon Vineyards near Junction City to see how new vines get their start—or watch biodynamic farming at its best at Antiquum Farm Tasting Room, where farmers utilize the help of pigs, sheep, geese, and a vineyard dog or two to keep the grounds pest-free and fertilized.
Arrive in Eugene, and ditch the car by walking, biking, or scootering to urban wineries and craft breweries in downtown and in the artsy Whitaker neighborhood.
Check into the downtown Graduate Eugene, The Gordon Hotel, or Inn at the 5th for a convenient stay in subtle luxury while surrounded by casual and fine dining options. “Farm to fork” is nothing new on the dinner menu at Marché (celebrating 25 years of delicious and inspiring meals), the rooftop bar at Carlita’s pairs its flavorful margaritas with sweeping views, and Lion & Owl puts a locally sourced spin on comfort food fare from inside a renovated Airstream trailer. Finish the day with a nightcap at 86 Speakeasy, which requires advance reservations for the secret code to get in.
Day 4: Relax With Wine in Roseburg, Hot Springs in Ashland (Eugene to Ashland)
Start your day with flaky biscuits at Magpie Coffeeshop, or stroll a few blocks for a Liege waffle from Off the Waffle. If visiting on a Tuesday or Saturday, check out the Lane County Farmers Market in downtown Eugene for fresh produce, baked goods, and organic meats and fish. Don’t forget to pick up food for the road at Provisions Market Hall—or stop into Creswell Bakery for decadent cinnamon rolls as you leave town and head south.
Continuing south from Eugene, you will enter the Umpqua Valley—where travelers can peruse wineries, eateries, and specialty culinary stops along the Great Umpqua Food Trail. In Roseburg, just an hour south of Eugene, pair your wine tasting at Melrose Vineyards with a curated selection of local treats. Continue south on I-5 to the charming city of Ashland, home of the Oregon Shakespeare Festival. Spend the night at Lithia Springs Resort, where thermal hot spring water is piped directly into your room. When you’re done relaxing, enjoy wines from the celebrated Rogue Valley and Applegate Valley at the on-site tasting room.
Looking for an offsite dinner or tasting? Visit the nearby Irvine & Roberts Vineyards, where the tasting room offers spectacular views of the broader Rogue Valley—as well as an award-winning wine selection, curated menu of light bites, and vineyard-to-table meals.
Day 5: Pick Up Local Bites to Enjoy Back Home (Ashland to Medford)
Start your day along the Rogue Valley Food Trail—a self-guided selection of the best food and culinary experiences the Rogue Valley has to offer. Rogue Creamery’s cheese shop provides world-famous blue cheese, while Jefferson Farm Kitchen in Jacksonville offers an assortment of small-vendor and craft selections. (Be sure to save room in the suitcase so you can remember your Oregon trip from the comfort of your kitchen.) Fly out from the Rogue Valley International Medford Airport (MFR), just 30 minutes north of Ashland, which offers direct flights to Los Angeles and convenient connections.
