Do you prefer your wine tasting with food pairings, live music and supporting great causes? Oregon offers that all year-round but really steps it up during Oregon Wine Month in May, which culminates in a grand Memorial Day Weekend finale at tasting rooms in all corners of the state. Oregon’s winegrowing regions are full of accolades, the latest one ranking the Willamette Valley as No. 1 among the World’s Top 10 Wine Destinations for 2025, by VinePair. The ranking cites Oregon’s longstanding calling card of world-class pinot noirs, now with additional layers of excellence — “booming with diverse projects that celebrate a wide range of grapes, from chardonnay and gamay to syrah and chenin blanc,” as well as being a premier destination for stellar biodynamic and sparkling wines.
Wherever your wine adventures lead, know that Oregon wines fly free on Alaska Airlines, so you can take a bottle of Oregon wine country home with you.
Here are our top tips on how to uncork and join the party.
Attend Wine Events
If you’re looking to level up your wine-tasting experience, consider checking out any of the special events featuring Oregon wines in May and beyond.
One of the hottest tickets of the year is to the Oregon AAPI Food + Wine Fest, founded in 2023 with the mission to celebrate the state’s diverse wine and culinary scene. Expect two days packed with delicious bites and flights from popular AAPI-owned restaurants and wineries at Stoller Family Estate’s Experience Center in Dayton.
Head to McMinnville and mingle with 40+ small-batch, independent producers at the Indie Wine Mixer in late May. Hosted at Ricochet Wine Co., this 2-day event celebrates wines born from grit and passion projects, led by upstart producers often working on a shoestring budget. Another springtime celebration not to miss is Pink! Rosé Festival in Hillsboro, where nearly 30 Tualatin Valley wineries serve tastings of their favorite summer sippers.
In Central Oregon, the month-long Sunriver Resort Food & Wine Festival is a gastronomic celebration through May that includes wine-paired dinners, blind tastings and cooking classes.
If your travels go beyond Oregon Wine Month in May, plan ahead to attend Savor Southern Oregon in June, a two-day festival in the historic town of Jacksonville that brings together the largest gathering of Rogue Valley wineries along with expert-led workshops, guided tastings and access to rare and limited-edition bottles. For sparkling wine enthusiasts, don’t miss Method Oregon in July, this inaugural event is dedicated to the state’s traditional method sparkling wines with tastings, panel discussions and more.
See the Oregon Wine Board’s event calendar here.
Savor Food and Wine Pairings
From local cheese and charcuterie to seasonal pasta and tasting menus, there’s nothing quite like a bottle of Oregon wine paired with your favorite foods. You’ll find many places to enjoy unique wine-pairing experiences in Oregon. Most tasting rooms offer opportunities for noshing, but many Oregon restaurants and wine bars also offer exceptional wine selections. Top spots for wine-paired dinners in Portland include Arden Restaurant, OK Omens, L’Orange and Heavenly Creatures.
In the North Willamette Valley — southeast of Portland — you can relish the newly renovated dining space and extensive wine lists at JORY at The Allison Inn & Spa and romantic meals at The Painted Lady Restaurant in Newberg. Or head to McMinnville for exquisite pairings at Humble Spirit, La Rambla and Pinch.
In the Columbia River Gorge, Riverside offers sensational waterfront dining and a Gorge-focused wine list and Solstice Wood Fire Pizza serves up show-stopping pies alongside local wines.
There’s no shortage of wine-centric restaurants in Southern Oregon, too. Try fresh pasta Gogi’s Restaurant in Jacksonville and fine dining at Ashland’s popular Alchemy Restaurant and Bar.
Do Good for the Community and Planet
As you choose where to wine taste or buy bottles of your favorite Oregon wine, there are numerous places where your dollars will make a difference. It’s a great opportunity to support Oregon’s diverse winemakers and leaders in the industry like Tiquette Bramlett, founder of Our Legacy Harvested – an incubator that works to advance opportunities for BIPOC individuals in the wine industry. Some wineries even donate a portion of their sales or tasting room fees to ¡Salud!, a program that provides healthcare to vineyard workers and their families.
A longtime leader in environmental stewardship, you can support Oregon’s eco-friendly wineries – those dedicated to leaving the planet better through sustainable farming and winemaking practices. For instance, Soter Vineyards — a biodynamic vineyard in Carlton that is devoted to holistic farm management practices — donates $1 from each bottle of their Planet Oregon pinot noir to the Oregon Environmental Council to support the nonprofit’s work towards climate resilience. Or look for Salmon-Safe certified wines, a program growers adopt to protect and restore salmon habitat. Oregon also has the most B Corp wineries in the world, a global certification that uses business as a force for good.
Visit a New Wine Region
Oregon is home to 23 winemaking regions, each with terroir as diverse as the landscapes. If you’ve been to the North Willamette Valley (towns like Newberg or Dundee), why not try the Mid-Willamette Valley (Salem and Corvallis area) or South Willamette Valley (near Eugene)? Each beautiful region has their own unique character with friendly winemakers and gorgeous tasting rooms both in the city and in more rural areas.
Southern Oregon is home to the state’s other esteemed wine region and is perfect for wine-paired adventures. Check out the scenic Bear Creek Wine Trail (Central Point to Ashland), and the wineries and wildflower hikes around Grants Pass, Rogue Valley and Applegate Valley. Three cheers to the Rogue Valley for landing on USA Today’s 10 Best Wine Regions in 2024 and Ashland’s Winchester Inn securing a spot on the list for 10 Best Wine Country Hotels.
The Columbia River Gorge is home to stunning wineries and landscapes as well; both Analemma Wines in Mosier and riverfront Tierra de Lobos Winery in The Dalles are part of the East Gorge Food Trail and are stunning places to visit after a nearby hike or a U-pick fruit adventure. Travel just a bit further east to Milton-Freewater to experience the Rocks District — an enclave of tasting rooms that have sprung up in recent years to showcase the famous Walla Walla Valley terroir.
Book a Tour and Go Car-Free
Love wine tasting, hate worrying about the drive? Don’t fret, that’s exactly what Oregon’s wine tours are here for. Expert guides across the state offer a variety of transportation options, from private car services to luxury vans or shuttles like Carlton-based NW Wine Shuttle, which offers everything from itinerary support to hourly transportation. Or, you can pedal your way through wine country on a tour with Wine de Roads. When you go with a guide they’ll curate the best possible trip and take care of all the details. They’ll also share stories about the wine region and may introduce you to the makers or include special tours of the vineyards or cellars. For more tips, visit this guide on how to go car-free in the Willamette Valley.
Find out more about Oregon Wine Month, including special tastings, events and specials around the state at OregonWineMonth.org.
