Oregon’s most popular wine grape—cranberry-and-clove-redolent pinot noir—is notoriously thin-skinned: hard to cultivate, quick to overheat, skittish when pressed. On the shelf, this capriciousness can translate to sticker shock for bottles from the Willamette Valley’s best-known pinot masters. When you find affordable Oregon pinots, you can often thank fruit grown in the less-flashy valleys farther down I-5.

Each year, the sprawling Southern Oregon AVA—stretching from Elkton (located an hour southwest of Eugene) all the way to the California border—ships more than half of its annual grape harvest, predominantly pinot noir, to winemakers in the Willamette Valley and beyond. But until recently, Portlanders have been slow to recognize that this reliable, humble supplier’s five sub-AVAs—which together grow more than 70 varietals—are actually offbeat wine destinations in their own right.

Take the Rogue Valley AVA’s newly minted Bear Creek Wine Trail, which links a dozen wineries from Medford to Ashland on a 22-mile route that hopscotches the highway more than five times. Range is what you’ll find along the state’s southernmost wine trail: both in the pours (everything from pinot to gewürztraminer and viognier) and in the personalities that fill these very different tasting rooms.

Make camp for your journey in the historic gold-mining outpost of Jacksonville—a perfectly preserved western town ringed with madrones and autumn-tinted maples. From here, follow the wine all the way to Ashland, home of the world-renowned Oregon Shakespeare Festival. Toast your day Shakespeare’s way—with an evening of theater (several OSF productions run through October, including UniSon, based on poetry by August Wilson, and the Bard-inspired Off the Rails) and a chalice of wine to “bury all unkindness.”

Your One-Day Wine Trek

Start with a full breakfast in Jacksonville, then warm up with a stroll through the Jacksonville Woodlands—18 miles of trails that literally wrap around town. Next, hit the Bear Creek Wine Trail with a first stop at stucco-terraced DANCIN Vineyards, where you can nab wine trail passports along with wood-fired pizza. From here, the specific route is yours to plan. Zigging north toward Medford? Stop at RoxyAnn Winery’s big whitewashed barn. Sticking to the country roads south of 99? Try a trio of tasting rooms near Talent—Pebblestone, StoneRiver, and Aurora Vines. Near trail’s end, find Weisinger Family Winery south of I–5, and the grandiose Belle Fiore Winery just north, in the soft hills above Ashland. Sweeping valley views are a few miles further, at Irvine and Roberts’s brand-new tasting room (too new to make this year’s passport). If the play’s the thing while in Ashland, consider tickets to Jiehae Park’s hit OSF world premiere Hannah and the Dread Gazebo. Still thirsty? For your second day, go west: the Applegate Valley Wine Trail starts right on the other side of Jacksonville. 

Food/Lodging in Jacksonville

Since 1861, the Jacksonville Inn has matured (just like you-know-what) into dusty luxury, with eight brick-walled guest rooms and four opulent “cottages” two blocks away. (As a bottle shop, the hotel’s red-carpeted “lobby” is pure gold.) The inn’s subterranean restaurant offers fine dining by candlelight, or stroll a few blocks west (past a veritable saloon) to Gogi’s Restaurant for upscale New American cuisine.

Food/Lodging in Ashland

Enjoy your pick of perches, from the luxe Peerless Hotel to camping at nearby Emigrant Lake. Pair Rogue Valley wines with farm-to-table fare at Larks—or local ales and lamb burgers at Standing Stone Brewing.