Trip 1: Gaston & Highway 47

From the Washington side of the Columbia Gorge to the new Van Duzer Corridor American Viticultural Area near Salem, there are roughly a dozen distinctive grape growing regions within an hour or so of the city. Find some of the closest in the hills around Forest Grove and Gaston, just south of US-26.

No matter where you go, a COVID-era wine country trip takes some planning, with many tasting rooms operating by reservation only to avoid any crowding, though walk-ups are sometimes allowed when there’s room. Some spots allow access only for members of their wine clubs (membership is generally just a commitment to buy a few bottles a year), while others—like Plum Hill Vineyards, which has a “pampered puppy play area” in addition to its patio strung with grape lights and warmed by a brick fireplace—will let anyone and their dog book a tasting. At the Tuscan-inflected Apolloni Vineyards, guests can book two hours on the bocce court and play while they sip full-bodied pinot noir. Known for its bubbly, Kramer Vineyards was mid-renovation on its tasting room when the pandemic closures hit, so it was a good time to push service outside to its dahlia-lined shaded patio. Guests can also take a glass to a dispersed seat amid the Müller-Thurgau or chardonnay vine rows. It can be hard to choose between an indoor or outdoor spot at Saffron Fields Vineyards in Yamhill; the tasting room doubles as an art gallery, and the grounds are home to a classically designed Japanese garden.

For a well distanced overnight, check out the Beacon Hill Cabin, perched across the vineyard from Beacon Hill Winery’s tasting room. Like a fire lookout with a much easier climb up, the cabin’s second floor has just a bed and wraparound windows, while its cozy ground floor features a wood-burning firehouse and a very efficiently laid out tiny kitchen. (The bathroom is not attached to the cabin—bring a robe for the quick dash outside.) Find plenty of other distanced lodging options on Airbnb, including a glampy tent platform surrounded by goats just south of Cornelius.

Is a drinker who’s not that into wine tagging along? They might enjoy a stop at Forest Grove’s SakéOne craft sake brewery. If all else fails, just drop them at the One Horse Tavern in downtown Gaston for a burger, live music on the patio, and a “May the horse be with you” souvenir beer koozie. —Margaret Seiler

Trip 2: 99W & Newberg

Highway 99W spins out of the metro area, weaving under I-5 and over 217, bypassing the quaint downtowns of swallowed-up suburbs to leave drivers staring at strip malls and traffic lights. But then, just past Sherwood, we’re suddenly shot through a green tunnel of tree canopy and out into another world. Blue signs point to farms just off the highway (and to a farmhouse brewery, Wolves and People). There’s the classic 99W Drive-In. And the surrounding hills hide wineries and vineyards galore.

Think of this year’s practically mandatory reservations not as an inconvenience but as a chance to plan and hone. Maybe zero in on wineries involved in this fall’s Celebrating Hispanic Roots (September 15–October 15, celebratinghispanicroots.com), including biodynamic-focused Cramoisi Vineyard in Dundee and Yamhill’s Atticus Estate Vineyard & Winery, which offers private tastings in both English and Spanish.

Distancing is easy at Durant Vineyards, where tasters can book a wine cabana, accessed with a quick ATV ride, for a private picnic among the grapes. You can even sleep among the grapes by renting out the two-bedroom Stoneycrest Cottage, a plush pad with a wraparound porch. (While you’re there, book an olive oil tasting, too: oilioteca Durant Olive Mill opened in 2008.) Another overnight option is The Vintages in Dayton, where well-appointed classic trailers mean you’re not sharing space with any fellow travelers.

Through the end of September, get an extra early start on the weekend by timing a trip to catch the Wednesday-evening Newberg Farmers Market, where you can stock up on late-summer produce for trip snacks and share a market pizza from Hook N Ladder, a wood-fired brick oven mounted on a fire truck. Year-round, Newberg’s strollable downtown has not one but two combo bar and toy shops: a chalkboard of local and regional beers shares wall space with Dixit, Settlers of Catan, Tokaido, and other board games at Barley & Vine, and the shelves of local wine bottles giving way to Bruder trucks and kid activity sacks at Social Goods. Break up the boozier stops with a peek into Chapters/Cream Northwest coffeehouse/bookstore/scoop shop; Velour, a vintage-and-new clothing store where you might find an old Jantzen swimsuit, a wool watch cap, and some perfectly broken-in overalls; or Antique, Freak & Flea, a secondhand shop with an emphasis on the Freak. —MS

Trip 3: Stay in Town

Oregon’s wonderland of wine destinations isn’t just picturesque, vineyard-lined hills and barn-dotted landscapes. It’s easy to take a wine tour (and even a world tour) without leaving the city at all. Here are a few spots to add to an urban itinerary.

“There’s always something different open every night,” says sommelier Trevor Gorham, who helps helm Montavilla’s charming Vino Veritas, a wine bar and bottle shop. Owner Sami Khawaja offers a standing $16 flight option that allows you choose from three of the dozen-plus glass pours available. Offerings change regularly and reflect the seasons—“chilled white wines and warm weather reds in the summer,” says Gorham, “transitioning into more fuller-bodied reds when the weather is cold.”

There are outdoor tables for the intrepid urban wine tourist, or if you’d rather explore from home Vino Veritas offers local delivery. With choices like Troon’s sparkling Piquette! from the Applegate Valley and a chenin blanc by Idiot’s Grace in the Columbia Gorge, you can explore the world of wine without leaving your couch.

In Northeast Portland’s Concordia neighborhood, Jane Smith’s Dame has built a national reputation for its cutting-edge natural wine program, but also for eclectic food, atmosphere, and intimate service. If you’re new to natural wine, this is a great place to start; if you already know your way around a trendy wine list, Dame rewards with a deep menu of hard-to-find cult bottles. Each of the 12 nightly glass pours is also offered by the half-glass (it should be a law), which means you can start slow, maybe with with a small-producer Piedmontese Barbera, before moving on to the avant-garde wines of Slovenia, Croatia, and the Republic of Georgia. There’s also same-day delivery, and a “storage container wine shop” Smith is planning for the space between Dame and Beast, with outdoor seating.

In a parking garage renovation project at SW Ninth and Morrison funded in part by Prosper Portland, The Crick PDX is a downtown offshoot of the North Plains tasting room for Abbey Creek Winery. The Crick PDX offers tasting sessions by reservation to try Bertony Faustin’s exceptional late-harvest gewürztraminer, pinot noir blends, and juicy chardonnay.

No Portland urban wine tour is complete without a visit to an urban winery, and SE Wine Collective is the city’s best. Not only have founders Kate Norris and Thomas Monroe built their accomplished Division Wines label in this space, they’ve also established an ever-growing troop of resident winemakers and alumni working on the collective’s shared facilities. Amid pandemic uncertainty and the space needs of the fall harvest, house eatery Oui! Wine Bar & Restaurant is going on “indefinite hiatus” starting in September, but bubbled-together groups of up to 10 can book the collective’s space for private tastings and get a look at harvest season in action. —Jordan Michelman