Seamlessly blending Old West romance, swoon-worthy syrah, and farm-fresh menus, the Applegate Valley is making a strong play for Oregon’s most charming AVA. You’re overdue for a weekend in this rugged, sun-drenched stretch of meticulously tended vineyards. Your launchpad: Jacksonville, a former gold-mining town with plenty of modern comforts. Your mission: 18 wineries in 20 miles.

Day One

Pit Stop #1: Cheese & Chocolate

Take a break from the highway and indulge in ample on-the-road sampling in Central Point, Oregon. Whet your appetite with dozens of handcrafted blue cheeses and wedges of sharp farmhouse cheddar at Rogue Creamery (311 N Front St, Central Point), then duck in next door at Lillie Belle Farms (211 N Front St, Central Point) to load up on bacon caramel bonbons and almond and hazelnut praline bars.

First Sips

Unwind from the morning drive (and complement that cocoa binge) with a flight of syrah, viognier, and some of Southern Oregon’s best rosé at Quady North (255 California St), Bonny Doon veteran Herb Quady’s Jacksonville tasting room.

Pre-Dinner Shopping Stroll

California Street is Jacksonville’s main drag, lined with restaurants and boutiques unified by turn-of-the-century, pioneer-town façades and chock-full of Remy leather jackets, locally designed silver jewelry, and organic candles. Ground zero for culinary retail therapy? The Pot Rack (140 W California St), offering an eye-popping array of kitchenware, knives, and cookbooks.

Garden-to-Table

Dining Owned by brothers Gabriel and Jonoah Murphy, Gogi’s Restaurant (235 W Main St) offers a lavish dinner with an unmistakably local soul. Much of the produce is grown on the Murphys’ farm, and vineyards just minutes down the road dominate the wine list. You’ll find the best seats in the house on the sunny patio, flanked by aromatic planter boxes of nasturtium, lavender, and oregano.

The Nightcap

March your road-weary feet to the new Adit Public House (150 S Oregon St) for a proper nightcap. A row of midcentury refrigerators forms the centerpiece of this convivial wine and beer bar, each equipped with a kegerator tap spouting rare Southern Oregon brews like Walkabout’s Worker’s Pale Ale and Arch Rock’s State of Jefferson Porter. 

Day Two

Late Brunch

Calling C Street Bistro (230 E C St) “intimate” would be an understatement. Cozy up to your neighbors at one of the three communal tables and dive headlong into chef Paul Becking’s decadent creations: duck confit–topped herb waffles, smoked-salmon-cake sandwiches, and the juiciest burgers in town, ground to order. 

Picnic Prep

Stop by Jacksonville Mercantile (120 E California St) to stock up on local cheeses and imported olives, then visit Gary West Meats (690 N Fifth St) for Wagyu beef jerky and tender smoked buffalo strips.

Wine Tasting

The $20 Applegate Valley Wine Passport earns you seven days of free tastings. (Yes, you read that right.) With 18 wineries to tackle within 20 miles, you will not leave thirsty.

Highlights include Rhône varietals from the biodynamic-certified Cowhorn Vineyard (1665 Eastside Rd, Jacksonville), viognier in the century-old haybarn-turned-tasting-room at Valley View Winery (1000 Upper Applegate Rd, Jacksonville), tempranillo on the riverside porch at Red Lily Vineyards (11777 Hwy 238, Jacksonville), and horse-drawn carriage tours through the vines and gardens at Schmidt Family Vineyards (330 Kubli Rd, Grants Pass).

Finish at Wild Wines (4550 Little Applegate Rd, Jacksonville), where Carla David makes wine from foraged flowers, fruits, and herbs like dandelion and rosehips. 

Moveable Feast

Tuck into your provisions in the shade of native laurels and pines at the 88-acre, river-fronting Cantrall-Buckley Park (154 Cantrall Rd, Ruch; $4 day use fee).  

Sushi—with a Side of History

Head back to Jacksonville for dinner at Umi Sushi, a low-key Japanese restaurant in the historic former home of Beekman Bank, one of Oregon’s first financial institutions. Choose from build-your-own bento boxes, savory beef short ribs, and cold soba soups in addition to the requisite rolls and sashimi.

Day Three

One for the Road

Stock up for the journey home with fresh pastries, local berries, and wildflower honey at the Jacksonville Farmers Market, a small-town souk held every Sunday from 10 a.m.
to 2 p.m. on the lawn of Jacksonville’s historic downtown courthouse.

Where to Stay

← The TouVelle House Bed & Breakfast (455 N Oregon St, Jacksonville; touvellehouse.com) is an immaculately restored 1916 craftsman with six well-appointed rooms, a sprawling garden, and a private saltwater pool. Breakfast is plentiful and made from scratch using local ingredients. From $169

Looking for a dose of modernity amid all this country charm? Check into one of the three Élan Guest Suites (245 W Main St, Jacksonville; elanguestsuites.com). In addition to rooms with high-tech amenities, hardwood floors, and ample natural light, Élan also houses a gallery packed with Southern Oregon artists. From $220

HIT THE ROAD

Pack: A picnic blanket, a wine key, and a swimsuit for impromptu river swims

Hot Tip: Keep club soda on hand for stubborn wine stains. (Blot, don’t rub!)

Soundtrack: Ride Out the Dark, the debut LP from Portland band Houndstooth, serves up surf-era nostalgia rock perfect for late-summer vineyard drives.

Staycation: Looking to dip into wine country without a four-hour drive? Start with this year's wine harvest parties.