: John Valls / Oregon Wine Board

Top Spots for Wine Tasting with Friends in Southern Oregon

Mellow tasting rooms, stunning scenery and wines for every palate await in Southern Oregon.
April 11, 2025

The only thing better than wine tasting? Wine tasting with friends. Four hours south of Portland and home to its own international airport, Medford is the perfect home base for a wine-tasting getaway everyone can enjoy. Surrounded by rolling farmland, scenic views, rivers to raft and numerous hiking trails, Medford offers travelers a wide array of options — plus easy proximity to the Rogue and Applegate valleys, where more than 70 grape varieties thrive. That means uncrowded tasting rooms serving a vast array of wines for every palate, from elegant sparklers to full-bodied reds. Here’s where to take your crew on your next laid-back wine-tasting getaway. Whether you and your friends walk, roll or stroll, it’s easy to get around in Medford. Wheelchair accessibility is available at most wineries and on the streets in each town. 

Picnic tables line a calm river.
Red Lily Vineyards (Photo by John Valls / Oregon Wine Board)

Sip Riverside Rosé or Enjoy Sunday Supper in the Applegate Valley

Just west of Medford is the Applegate Valley, a stretch of sparkling riverbanks and steep forested slopes with vineyards around every bend. About 15 miles southwest of downtown, you’ll find Quady North. Make a reservation for a guided flight of estate-grown blends, including many varieties from Southern France like syrah, grenache, and an especially silky and elegant viognier that thrive in Southern Oregon’s long, warm growing seasons.

Just a couple of miles west on Highway 238 is Red Lily Vineyards, which offers a light lunch menu with treats like local cheeses and grilled panini, as well as the chance to lounge on the scenic banks of the Applegate River while sipping a glass of the refreshing Lily Girl rosé. Eight miles farther west is the biodynamic Troon Vineyard & Farm, which offers tastings as well as a weekly three-course Sunday supper featuring paired wines and produce grown right on-site. 

Wine bottles and glasses sit on a wine barrel.
The Punch House (Photo by John Valls / Oregon Wine Board)

Get Cozy by the Fire in the Upper Rogue Valley

The Upper Rogue Wine Trail is a cluster of six wineries that spans a scenic arc of the Rogue Valley directly north of Medford. One of those is Kriselle Cellars, which welcomes guests by appointment year-round. Snuggle up by the fire with a cozy blanket or sit under the refreshing water mist on a sunny day. The winery produces several varieties, including a show-stopping sauvignon blanc. 

In search of something richer? Look no further than Cliff Creek Cellars, which is known for big, oak-aged red wines. Try the claret and savor its dark-spice notes. Top off the day with a visit to boutique winery The Punch House, named after the first small building where grapes transformed into wine. These wineries are open for tastings year-round, but May is an especially good time to visit. The annual Roam the Rogue tasting event, usually in early May, is a timely kickoff of Oregon Wine Month

A brightly-painted mural showing blossoms and pears.
The "Oregon Mural" in downtown Medford (Photo by Jak Wonderly / Travel Southern Oregon)

Murals, Blue Cheese and Festival Fun in Jacksonville and Medford

Five miles west of Medford, Jacksonville is a historic mining town now more famous for wine than gold. Today it’s a cultural hub famous for the annual Britt Music & Arts Festival, as well as its walkable downtown lined with well-preserved 19th-century architecture, art galleries, dining establishments and boutique shopping — plus plenty of opportunities for wine tasting.  

Some of the region’s favorite producers — like DANCIN Vineyards, Hummingbird Estate and Dos Mariposas Vineyards & Lavender Farm — are located within a few miles’ drive. Padigan Wines‘ frequent live music might get you on the dance floor if you’re not careful. RoxyAnn Winery is on the National Register of Historic Places for its 1917 colonial-style residence and its legacy pear and apple orchard. Honor Barn Red — a blend of merlot, cabernet sauvignon and syrah — is one of its best-selling wines. It’s a lot to take in on a single visit, so mark your calendars for the Savor Southern Oregon wine festival, typically held each June in Jacksonville. 

Back in Medford, take in a self-guided walking tour of 12 meaningful murals around town that celebrate the region’s history and culture. You can also head to Rogue Creamery in Central Point for samples of award-winning cheeses, including the seasonal Rogue River blue made with syrah leaves from Troon Vineyard. Or visit one of the many year-round Rogue Valley farmers markets to stock up on local produce, baked goods, flowers, crafts and more. 

Then head back to your hotel to rest up. With 35 hotels and 250 short-term rentals, there are plenty of places to stay in Medford. One great option for families and groups is the island-style Compass Hotel by Margaritaville, which has an on-site pool, bar and restaurant.

About The
Author

Estelle Rogers
Estelle Rogers lives in McMinnville, where she's been appreciating pinot noir over the past three decades. She enjoys slow travel, wine and great dining experiences, and has written for publications like Oregon Wine Press, 1859, AAA's Via, and NW Travel & Life Magazine.

Trip Ideas