Indeed, there was a time when the town’s quaint soul was threatened. In 1964 the Oregon Highway Commission sought to redirect Highway 234 through downtown. Residents threw a fit—and then they got creative: By petitioning to designate Jacksonville as a National Historic Landmark, they realized they might be able to keep the bulldozers at bay and thus preserve their original architecture. After a successful campaign, the town was named a National Historic Landmark City in 1966.

“We went from sleepy ghost town to bona fide tourist attraction,” says Scott Clay, of the town’s chamber of commerce. “It probably saved us from extinction.”

The designation means that Jacksonville is subject to reviews by the National Park Service, which requires the city to (agreeably) enact strict design-code ordinances. Meeting these standards was challenging for Mike Thornton, who recently built Britt Cottage, a bed-and-breakfast on Third Street. But the hard work paid off: Although the cottage is new and outfitted with flat-screen TVs and Wi-Fi, the Craftsman-style structure fits seamlessly into the town’s aesthetic. “[These codes] are good for business,” says Thornton, 48.

Strolling along California Street today, this seems especially true. There are almost a dozen restaurants nearby, where 20 years ago only the Jacksonville Inn and the burger joint Bella Union were thriving. There are also high-end boutiques, and across the street, a wine-tasting room, South Stage Cellars, housed in an 1865 brick cottage.

“Theater people from Ashland are staying in Jacksonville now,” says South Stage’s owner, Spirit Lount, 37. “You can’t corner the tourism market with a ‘corporate’ perspective. It’s all about charm.”

Jacksonville can now add wine to its list of alluring qualities. And having tasted a delectable viognier made by local winery Valley View, my interest is piqued. On my last day in town, I venture eight miles north on Highway 238 to explore the Applegate Valley Wine Trail, and within a minute, I am driving through an agrarian landscape of orchards, vineyards, and alpaca farms.

Just after the tiny town of Ruch, I turn left onto Applegate Road and see Valley View, the oldest of the area’s 13 wineries. The winery is owned by brothers Mike and Mark Wisnovsky, whose father, Frank, seeking his own brand of gold rush, moved his family here from New Jersey in 1972 to plant grapes. “With a thriving wine country a few miles away,” says Mark, 44, who lives in Jacksonville with his wife and two kids, “we’re the town that has everything.”

An hour later, I am back on California Street sitting in Jacksonville’s first (and only) sushi joint, Jazushi. I ask its owner, Sunni Suzuki, why she chose Jacksonville, of all places, to open a sushi restaurant. “I’d been here once before to visit family,” Suzuki says. “And I loved it so much. It is just so charming.” I had to agree.