One Of 'America's Coolest Towns' Is A Historic And Charming Wine Country Gem On The West Coast

From the Willamette Valley, whose wine country is just as scenic as Napa Valley without the crowds, to the Columbia River Gorge, the secret wine region full of rare varietals and edgy, innovative blends, Oregon is filled to the brim with vibrant vino destinations. Tucked into the heart of the Rogue Valley in Southern Oregon, Jacksonville offers a charming retreat for wine lovers in a historic small-town setting. Surrounded by family-owned vineyards, cozy tasting rooms, and world-class wineries, you'll find plenty of sip-worthy spots, many of which you can explore on the Applegate Wine Trail.

History buffs will appreciate the area's Gold Rush Era roots, which are immortalized in the town's buildings and landmarks. In fact, the whole town is a designated National Historic Landmark, boasting walking tours, haunted ghost tours, museums, lovingly preserved 19th-century homes, and Western-themed buildings housing a variety of restaurants, shops, and inns. Named "One of America's Top 10 Coolest Small Towns" by Frommers (via the town's website), Jacksonville promises undeniable charm complimented by the flavors of one of Oregon's most delicious wine regions.

Residing about 20 miles north of Ashland and nearly 300 miles south of Portland (the trendy city where you can order the best coffee in America), Jacksonville is best reached by car. Visit in the warmer months to avoid snowfall. Of course, one of the town's most popular activities is wine tasting, which can be enjoyed year-round. Situated at the gateway to the Applegate Valley Wine Region, Jacksonville is surrounded by premiere tasting destinations. 

Embark on the Applegate Wine Trail, which is comprised of 18 local wineries crafting a variety of vinos. Favorite stops include Red Lily Vineyards, an idyllic property bordered by the Siskiyou Mountains that specializes in Spanish-inspired blends, or the Quady North Winery Tasting Room, a family-run estate that pours some of the most delicious varietals in Southern Oregon.

In the heart of town, you'll encounter unique tasting rooms like Remotion Wine on Main Street, which is housed in the historic Orth House and offers three private suites for overnight stays. If you're looking for another spot to sip and stay, the Jacksonville Inn is a beloved town staple that boasts The Wine Lounge, a local bar offering a complimentary glass to guests staying in one of the property's gorgeous rooms.

Dating back to the Gold Rush Era, Jacksonville is rich in history. The best way to trace the town's roots is to embark on a walking tour. Departing from the Courthouse Square each Saturday at 10 a.m. from Labor Day to Memorial Day, the Historic Jacksonville Walk Through History Tour traverses through the town's homes and businesses on a one-hour adventure through time. Though the tour is free, donations are always welcome. For a journey through Jacksonville's paranormal past, book a Haunted History Tour. Choose between two bone-chilling nighttime strolls through Jacksonville on the second Friday of the month from June to September. The Courthouse Tour is perfect if you prefer stories of haunted brothels and deadly epidemics, while the Britt Hill Tour focuses on the town's murderous history and ghostly tales from Oregon's first Chinatown.

Even if you don't take a formal tour, wandering through Jacksonville's historic downtown district offers plenty to discover. Enjoy an afternoon of antiquing on California Street, which is dotted with vintage shops like Pickety Place and Trolley Stop Antiques. Afterward, settle into a beloved downtown eatery like Bella Union Restaurant and Saloon, which features delicious dishes with locally sourced ingredients and a bar that is well-stocked with craft beers and bourbons. 

If you're staying the night, the aforementioned Jacksonville Inn is a popular place to stay. You can also book a historic stay at the McCully House Inn. Tucked into an 1860 homestead, the charming bed and breakfast is the state's oldest home operating as an inn and is the perfect home base for an authentic Jacksonville retreat.