If struck with a sudden samosa craving while hurtling down Highway 26, pause in Hillsboro at Chennai Masala Indian restaurant for the excellent lunch buffet, or continue down NW Cornell Road towards Syun Izakaya for sushi and sake. In Forest Grove, slip into McMenamin’s Grand Lodge Hotel for a dip in the year-round soaking pool (non-guests $5 an hour), then curl up by the fire with a cappuccino, or perhaps something slightly stronger, in the Billy Scott Bar. If approaching wine country from the south, go by water—the Willamette River-forging Wheatland Ferry runs daily and will set you back $2 per car (cash or check only); after disembarking, head 10 minutes west to Brooks’ Amity tasting room, where you can pre-book an Everyday, Estate, or Ouroboros Experience, each offering a different perspective of the winery, including tastings, of course.
Darling small town Carlton, in the heart of the Yamhill-Carlton AVA, may only be three blocks long, but those three blocks will keep you well occupied during your weekend getaway. Grab ham and Swiss breakfast sandwiches on freshly baked ciabatta at Carlton Bakery, compile a custom cheese and charcuterie plate and listen to live music at The Horse Radish, and if it’s the weekend, take advantage of Republic of Jam’s Swanky Tastes, a sampling of sweet and savory bites made with the company’s jams. Or, after drawing straws to see who’s driving home, investigate Carlton’s claim to have, at twenty-two, the most tasting rooms per capita in the entire United States.
Via scenic OR-240, head for the red hills of Dundee, a small but mighty former railroad town turned winemaking mecca. Since you no doubt have quite a few stops in the Dundee Hills AVA planned, pre-fortify at Babica Hen Cafe with a sturdy brunch of benedicts and banana chocolate crunch waffles by the fireplace, or lunch at Red Hills Market, where you can sit down to a wood-fired pizza topped with burrata and truffle oil, pick up sandwiches and salads to go, or shop the well-curated housewares for non-liquid wine country souvenirs. If you like a white tablecloth with your wine, book the nine-course dinner menu at James-Beard-nominated Painted Lady, which features a special experimental winter dinner series every Wednesday night through the end of March.
A cork’s throw to the east, old-fashioned downtown Newberg hails. At Ruddick Wood, set in a renovated 1920s garage, chef Paul Losch tempts with lamb and sweet potato hash and hazelnut biscuits, a nod to the region’s deep filbert farming roots. Browse the books with a cup of Bespoken coffee in hand at Chapters indie book and coffee shop, sample blueberry-pinot ganache truffles at Honest Chocolates, shop the 200+ pinot noirs at Valley Wine Merchants, and catch a flick at the Historic Cameo Theater, sister theater to Newberg’s beloved 99W Drive-In. If you prefer saisons to syrahs, grab fish tacos to go at friendly Dos Mundos food cart, then pair them with one of the exemplary brews on tap at nearby Wolves & People Farmhouse Brewery, founded by award-winning beer writer and author Christian DeBenedetti and his wife Lila Martin DeBenedetti, a Kauai-born food publicist.
From Newberg, it’s about a half hour west to charming historic McMinnville, not including a stop at the Evergreen Aviation & Space Museum and adjacent Wings & Waves Waterpark (claim to fame: a water slide that shoots out of the genuine Boeing 747 perched on the roof). Once downtown, stroll the quaint main street before lining up with the locals at Community Plate for a heap of heritage pork hash topped with an amber-yoked local duck egg, washed down with a housemade chai or Annie’s Bloody Mary. After a little light boutique shopping and antiquing, pop into R. Stuart & Co. wine bar for a glass of bubbles, a cheese plate and a chat with delightful proprietress Maria Stuart. After on-foot wine and beer tasting in the town’s burgeoning Granary District, home to nearly a dozen wineries and breweries, plus Flag & Wire coffee roasters, take a break for smoked mozzarella-topped turkey melts at Valley Commissary. Or, wind along the back roads to venerable Coeur de Terre Vineyard or Maysara Winery, a bewitching biodynamic newcomer with a riveting backstory. Then hustle back to town for your dinner reservation at intimate date-night darling, Thistle, followed by a nightcap with a side of stargazing at the Rooftop Bar atop McMenamin’s Hotel Oregon, or a game of pool in the back bar of buzzy Nick’s Italian Cafe.
For a room with a view and all the creature comforts one could desire, look no farther than Newberg’s The Allison Inn & Spa, outfitted with a full-service spa, private art collection, and Jory restaurant, which boasts a James Beard Award-nominated wine program. In Dundee, sleep steps from your pinot noir and pork schnitzel at the pet-friendly Inn at Red Hills, perched above Babica Hen Cafe and Angela Estate Tasting Room. And in McMinnville, check into one of the eleven elegantly outfitted 3rd Street Flats, which woo with fireplaces, full kitchens and a prime downtown location. In May, downtown McMinnville will also welcome the Atticus Hotel, a thirty-six-room luxury retreat anchored by Bless Your Heart Burgers, the sister restaurant to the popular Portland eatery. And for the sensation of a spring break getaway without the endless backseat squabbles, wrong turns and potty stops, reserve one of the nineteen meticulously restored retro campers at The Vintages Trailer Resort in Dayton.