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Cozy Winter Wineries in Southern Oregon

Warm up with a glass or a flight of wine at these welcoming spots.

’Tis the season for cuddling up next to a fireplace with a richly flavored, warming glass of red wine. From the scenic wineries of the Umpqua Valley to the snug, softly lit urban tasting rooms of Jacksonville, here’s where you’ll find some of the coziest wine-tasting experiences in Southern Oregon.

Reustle Prayer Rock Vineyards

The Umpqua Valley

The northernmost of Southern Oregon’s wine regions, the Umpqua Valley has a diverse climate that makes it ideal for growing Oregon’s beloved pinot noir and pinot gris, along with warmer-weather varietals such as tempranillo. It’s also home to the oldest estate winery in Oregon, HillCrest Vineyard, where the first pinot noir in the state was planted. HillCrest’s indoor tasting room feels like a mix between an old tavern and a living room with soft lighting, wood paneling and a large area rug that makes the space feel particularly homey. 

The Secret Wine Society in nearby Oakland is another fab choice, serving local and imported wines — including mulled wine — along with cheese, charcuterie and desserts like Basque cheesecake. Built in 1895, the historic building with high ceilings and exposed-brick walls was once a saloon. Enjoy a glass pour or bottle purchase from a selection of over 200 possibilities as you lounge in lush purple-velvet chairs.For a particularly elegant experience, head to Reustle Prayer Rock Vineyards, where you can sip estate vintages in an elegant wine cave that’s reminiscent of a medieval castle. Pull up a seat under a chandelier in the Grand Hall, or share stories in one of the winery’s three catacombs — private, nook-like tasting areas. You can also book an inviting stay in the winery’s original tasting room and former carriage house, furnished with French antiques.

Weisinger Family Winery

Jacksonville and the Rogue Valley

The sunny Rogue Valley produces both cool- and warm-climate wine in and around Ashland, Medford and beyond. In the middle of it all sits the historic town of Jacksonville, where you’ll find plenty of little tasting rooms and wine bars within a short walk of one another. In the middle of it all, South Stage Cellars offers a wonderfully diverse selection of wines in a snug and intimate historic building with exposed red-brick walls and a pair of fireplaces to match — just be aware that they are closed in January. On the outskirts of Jacksonville, Rellik Winery features a beautiful tasting room with a mix of farmhouse tables and plush furnishings (think soft velvet chairs and tufted sofas). Curl up inside with a glass of viognier or sparkling grenache, or head out to visit the fluffy alpacas that call Rellik home.

Farther south in Ashland, Belle Fiore Winery welcomes visitors into a fairy-tale chateau, complete with luxe, borderline regal furnishings, though the more casual mezzanine level at the Pavilion Tasting Room is a cozier option with tables for two. For something with more of a friendly lodge feel, head over to Weisinger Family Winery. While the star attraction of the tasting room here is an expansive outdoor deck with views for miles, it also has a small indoor area complete with plush sofas and low ceilings where you can try out a tasting flight on a cold winter’s day.

Cowhorn Biodynamic Vineyard & Garden

The Applegate Valley

A subappellation of the larger Rogue Valley AVA, the Applegate Valley is known for its production of full-bodied wines in the Bordeaux and Rhone styles. It’s also a great region for winter wine-tasting, with comfy tasting rooms galore. Schmidt Family Vineyards is a great place to start, offering a wood-clad tasting room with a big stone fireplace, reminiscent of something you might find in the Swiss Alps. For a decadent experience, relax there as you sip one of the acclaimed dessert wines. The tasting room at Red Lily Vineyards is similarly cozy, with a rustic-chic ambiance created by ample use of unfinished wood. Settle into one of the plush easy chairs near the stone fireplace with a glass of tempranillo and you’ll feel like you’re in a friend’s living room. 

Just down the road, Cowhorn Biodynamic Vineyard & Garden’s compact tasting room brings the outdoors in, with big picture windows that make it possible to take in views of surrounding fields and mountains while staying warm and snug. Pair a flight of organic wines with wood-fired pizza from the on-site oven. After a winter break in December, they’ll be booking again in January.

Top photo: Schmidt Family Vineyards