Learn About Some of the Best Wineries in Southern Oregon, Plus Travel Logistics and Things to Do in the Region

Down near the California border, there’s a breathtaking stretch of Oregon where the wine is as good as anywhere else in the state. The Willamette Valley tends to get most of the credit, but if you’re after scenic terrain, superb wines, and charming small-town life, it’s best to head south. Southern Oregon is spoiled when it comes to good looks and winemaking prowess.

Travel Logistics

The drive from Portland is about four-and-a-half hours and a mostly pleasant drive but there are more direct routes. Travelers can fly into nearby Medford, about 12 miles away.

Ashland makes for fine headquarters, a city set just a stone’s throw from scores of great wineries and tasting rooms. The city of 22,000 is part college and theater town, part high country paradise, and home to the Shakespeare Festival and Rogue-River Siskiyou National Forest. The Rogue River Valley is the backdrop for dozens of wine producers, specializing in everything from Pinot Noir to Viognier to Rhone blends.

Exceptional Southern Oregon Wineries To Visit

Just outside of town is Irvine & Roberts Vineyards, with its stunning patio and tasting space nestled in a sea of foothills. Set up a tasting appointment here if you like estate Pinot Noir, Chardonnay, and the occasional lesser-known varietal like Pinot Meunier. Down the road is Belle Foire, an opulent estate inspired by French architecture. Set up with a wine pavilion and chateau-like structure, the winery also features vineyard tours. The European flair extends into Belle Foire’s wine lineup, which includes the likes of Barbera, Montepulciano, Tempranillo, and more.

Ask most wine types where to go next and they’ll likely drop the Quady North name. Herb Quady’s wines are beloved all over the region and the longtime grower and producer just opened a new tasting space just outside of the historic town of Jacksonville, about 25 miles from Ashland. On top of photogenic views of the Applegate Valley, guests are treated to lovely wines and charcuterie, if hungry. Quady North is behind some of the best Rosé (made with grapes like Counoise and Grenache) in southern Oregon, along with elegant Cabernet Franc and Syrah.

Down the valley on the outskirts of Grants Pass is Troon Vineyard, one of the eldest in the state. Launched in 1972, the winery focuses on mindful farming and is both Demeter Biodynamic Certified and Regenerative Organic Certified. In other words, it’s all about minimal inputs and celebrating the health of the soil, which gives rise to some truly outstanding wines. Look out for excellent Tannat, deftly-made blends and some great orange wines, made with grapes like Vermentino.

Back in Ashland, Weisinger Family Winery makes exceptional small-batch Gewürztraminer and Sauvignon Blanc, along with a grilling season favorite in Malbec. It’s a standout spot for Bordeaux and Rhone blends paired with amazing hospitality.

Fans of refreshing whites like Grüner Veltliner, Riesling and Pinot Gris are encouraged to head to Reustle Prayer Rock Vineyards, a bit north in Roseburg. They also make some intriguing port, sparkling, and dessert wines. It’s a considerable drive north but a great stop especially en route to Portland or the Willamette Valley. It’s part of the flourishing Umpqua Valley appellation, the other major growing area outside of the Rogue in this part of the state. If you go, be sure to pop into Abacela Winery, makers of fantastic Spanish-style wines.

Outdoorsy Things To Do

Wine ought to be in the foreground of your trip but you’d be letting the place down if you didn’t plan some one-of-a-kind outings. Oregon’s only National Park is an easy day trip from town and home to the impossibly blue waters of Crater Lake, the country’s deepest lake. There’s a postcard image in every direction and the old lodge is worth perusing, especially if you forgot to pack a lunch. There’s blue-ribbon rafting and hiking along the Rogue River, not to mention some fine fly-fishing, depending on the time of year.

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A closer trek is to the aptly-named Mt. Ashland, just 8 miles from town but a towering 7,500 feet in elevation. The air is pure atop the highest point in the Siskiyou’s and the panoramic views won’t soon leave your memory. While a snow bunny’s version of heaven, the peak also has its summer merits, like mountain biking, camping, and a robust trail system that includes part of the famed Pacific Coast Trail.

Dining and Lodging

Ashland Springs Hotel is easily the best in Ashland and stands out as a nine-story skyscraper amid the petite skyline. It’s a historic hotel beautifully restored and dating back to 1925, home to Larks Kitchen, with its impressive local wine list and fresh cuisine. Dining at the hotel restaurant is a time capsule experience, with little evidence of the modern era outside of the occasional glow of a patron’s phone. Grab a coveted seat on the sidewalk outside if you can.

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Jacksonville is just a few miles away and easily one of the best-kept secrets in the Pacific Northwest. The tiny town is an old western haunt preserved in mint condition (it’s where The Great Northfield Minnesota Raid was filmed). With its impeccable architecture and pedestrian-friendliness, you’ll want to ditch the car or bike for a few hours, at least. The Jacksonville Inn is the beating heart of this charming town, where guests can stay onsite or a few blocks away at one of several well-appointed cottages. Whether you overnight or not, a trip to the house wine shop is well worth your time, as is a meal at the top-notch hotel restaurant.

For a vineyard stay, check out the cottage at Weisinger, set in a modernized farmhouse that was originally built in 1920. Troon offers similar accommodations while Hummingbird Estate offers gorgeous guest suites in a restored mansion.

Other Ashland restaurants of note include the wine-centric Alchemy, convivial Skout (right near the beautiful grounds of Lithia Park), and the celebrate Cascadian cuisine of chef Josh Dorcak at MÄS.

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