Oregon’s wine-tasting rooms have always been places that inspire full-sensory delight — from the scenic mountain and vineyard views to the bright pop of a crisp rosé on a sunny day. As the warmer weather rolls in, wineries across the state are excited to celebrate Oregon Wine Month in May with an array of special events, including live music, wine-pairing and charcuterie board workshops, art walks and winemakers talks. However you choose to sip and explore, reservations are highly recommended for the best experience.

Cabanas, ATV Tours and VR Experiences
Those looking for an exclusive, private tasting experience are in luck — many of Oregon’s wineries offer premium, small-group experiences for wine enthusiasts who want to gather with a small group from the comfort of their own VIP-style cabana. In the famed Dundee Hills, Durant at Red Ridge Farms welcomes parties of four to book a private cabana for a two-hour slot, available May through October.
The visit begins with a scenic ATV ride through the vineyard and estate olive orchards, followed by a complimentary bottle of estate wine and a light picnic for four. Adelsheim Vineyard in Newberg reopens its seasonal cabanas in May. Perched near the estate gardens on a hillside overlooking the vineyards, the upscale cabanas seat up to eight guests. Reservations are best made alongside an estate tasting, though walk-ins may be accommodated based on availability.
At the iconic Stoller Family Estate in Dayton, enjoy an immersive tasting experience at the expansive Stoller Experience Center. Just steps from the vineyard, guests sip curated flights while exploring interactive tasting tables, augmented-reality art, large-screen video installations, and a virtual-reality experience designed to deepen wine knowledge in a fun, engaging way.
Also in Dayton, Joel Palmer House Restaurant stands as a fourth-generation Willamette Valley legacy destination, showcasing more than 600 Oregon wines dating back to 1994. An ever-evolving prix-fixe menu highlights the region’s seasonal bounty, expertly paired with some of Oregon’s finest pinot noirs.

Experience Oregon’s Diverse Wine Regions
Wine lovers can order the official Oregon Wine Touring Guide for maps and itineraries of all the state’s winegrowing regions, and for a limited time enter to win the Oregon Wine Month sweepstakes featuring airfare, lodging and curated wine experiences in the Willamette Valley or Rogue Valley.
For a do-it-yourself sip trip, venture off the beaten path to one of Oregon’s lesser-known wine regions. Sip the cool-climate wines of Elkton, a little community along the Umpqua River Scenic Byway, a stone’s throw from the beautiful Umpqua River. An ideal stop for road-trippers to the Oregon Coast or Southern Oregon, you can visit Elkton’s cluster of friendly, uncrowded tasting rooms within two miles of one another.
While in the Umpqua Valley, pay homage to Oregon’s oldest estate winery and the birthplace of pinot noir. HillCrest Vineyard in Roseburg, founded by Richard Sommer in 1961, is more than 50 years old. Sommer planted the state’s first malbec vines here, along with riesling and pinot noir. Nearby, Abacela is celebrated as Oregon’s tempranillo pioneer, planting the state’s first commercial tempranillo grapes in 1995 on its stunning estate outside Roseburg. Just south, you can also go wine tasting around the Rogue Valley, another compelling tasting destination, prized not only for its wines but also for its uncrowded outdoor activities — everything from hiking, biking and golfing to rafting, paddling and fishing.
The Dalles is another lesser-known region for wine tasting with vibrant tasting rooms like Tierra De Lobos, run by owner and winemaker Adolfo Ocheata Mollinedo. Come for the riverfront views, welcoming vibe and ample heated, outdoor space. As you travel along the Columbia River Gorge, you’ll retrace the path of the Missoula Floods and see how the dramatic geological event shaped the distinct terroirs of this region.

Wine Tasting Close to the City
Prefer to skip the drive and savor wine tasting closer to the city? Portland’s urban wineries make it easy to explore on foot, by bike or scooter, or via rideshare. Plot your own course among the PDX Urban Wineries, from Boedecker Cellars in Northwest to Hip Chicks Do Wine and Division Winemaking Company in Southeast; most recommend reservations. Don’t miss newish spots, including the downtown Domaine Serene Wine Lounge.
In Portland’s West Hills, Amaterra Winery delivers an elevated experience with afternoon tastings and full dinner service in the evenings. Just south and west of Portland, get inspired to enjoy Tualatin Valley wineries, along with Oregon’s two newest winegrowing regions, the Chehalem Mountains and the Laurelwood District.
And if you’re craving a getaway to sunny Bend, oenophiles will find plenty of fresh reasons to visit. The city is now home to a number of new tasting rooms including Bledsoe Family Winery, Stoller Wine Bar, Evoke Winery and Amaterra Kitchen + Social Club.

If You Go:
- Map out your Oregon wine tasting adventure with the official Oregon Wine Touring Guide — best of all, it’s free.
- When it’s time to take a taste of Oregon wine country home, remember that Oregon wines fly free on Alaska Airlines.
- Extend your trip with a vineyard stay in wine country, and round out your trip with memorable dining, hands-on farm experiences and stops along Oregon’s celebrated food trails.