A Weekend Winter Trip to Southern Oregon

Plan a winter trip to Southern Oregon for year-round delights

written by Jen Stevenson

Ward off winter-induced cabin fever by planning a road trip to Southern Oregon for a weekend of world-class theater, restaurant hopping, boutique browsing and wine tasting…plenty of wine tasting.

EN ROUTE: Culinary delights along the way through Southern Oregon


Zipping along the I-5 corridor between Portland and Ashland, scrumptious pit stops are plentiful. Rice Hill’s ever popular K&R Drive Inn slings old-fashioned cheeseburgers, thick-cut fries and Umpqua ice cream to a grateful lineup of road-weary travelers. The soccer-ball-sized cinnamon rolls at Heaven on Earth in Azalea have a cult following. Not to be missed—the tasty trio of Lillie Belle Farms artisan chocolates, Rogue Creamery and Ledger David Cellars, which share one delicious block in sleepy Central Point.

EAT + DRINK: Grant’s Pass, Jacksonville, Medford and Ashland


It’s all too easy to bypass Grants Pass, but pull over and stay a while—Ma Mosa’s dishes up a formidable house-brined corned beef hash and no fewer than nine signature mimosas, The Haul specializes in casual, beer-friendly bites and also serves as Applegate-Valley based Conner Fields Brewing’s tasting room, and the year-round Saturday Grants Pass Growers Market is one of the region’s finest.

Nestled between Grants Pass and Jacksonville, the scenic Applegate Valley is home to one of the state’s most intriguing wine regions. Sip biodynamic Rhône-style wines at Cowhorn, schlep your flight down to the Applegate riverbank at Red Lily, play checkers by the fireplace at Schmidt Family Vineyards, and toast glasses of tempranillo around the outdoor fire pit at Wooldridge Creek Winery, which also serves a cheese plate featuring its own CrushPad Creamery cheeses.
Best of luck finding better blueberry pancakes than the ones at Ashland’s Morning Glory cafe, where savvy brunchers queue up a few minutes before opening to bypass the rush. For a midday meal that will stick to your ribs, brave the both-hands-required house-cured pastrami sandwich at Sammich, then spend a long, leisurely evening with crispy sweetbreads, truffle-roasted game hen and a local pinot noir at Amuse.

Explore Medford’s thriving beer scene, with suds stops at Opposition Brewing Company, Portal Brewing Company, and Walkabout Brewing Company, then sample smoked blue cheese-stuffed lamb meatballs and baked manchego with quince sauce at eclectic Elements Tapas Bar. Fifteen minutes west of Medford, explore historic Jacksonville, a lively three-blocks-long town that has painstakingly preserved its Gold-Rush era charm. Browse the boutiques, sip syrah at the Quady North tasting room, dine on cider-brined pork chops at eclectic Gogi’s, then listen to live music at Bella Union.

10 Winter Destinations in Oregon


Ten Romantic Getaways in Oregon

Leave a Reply