In the heart of Southern Oregon’s Rogue Valley, Jacksonville offers the perfect blend of history, cuisine, and award-winning wines. Just a short drive from I-5, Jacksonville is conveniently located between Portland and San Francisco, and only 15 minutes from the Medford Airport—making it an ideal destination for a weekend getaway or extended trip.

A Wine Lover’s Paradise

Recently ranked the #2 Wine Region in the country by USA Today, the Rogue Valley wine region stretches from Grants Pass to Ashland, with over fifty wineries producing 70+ varietals. An array of micro-climates combined with Rogue Valley’s concentration of small, independent owners and winemakers means that no two wineries are exactly alike. Visitors can experience everything from robust Malbecs, Syrahs, and Tempranillos to crisp Sauvignon Blancs and sparkling rosés.

Jacksonville sits at the very center of this bounty. With tasting rooms just steps from the historic main street and surrounding estates easily reached by the Jacksonville Wine Trolley, visitors can enjoy a carefree day of sipping and sightseeing without ever getting behind the wheel. Just over the hill from Jacksonville, the Applegate Valley offers boutique wineries and scenic drives that wind past farms, rivers, and forested hillsides.

Jacksonville’s wine roots go deep. The motto of the Jacksonville Wine District is “Where Oregon Wine Began,” and it’s no exaggeration. As the wine trolley loops in and out of Jacksonville, you’ll pass the site of the first winery in Oregon, Peter Britt’s Valley View vineyard.

Living History

A National Historic Landmark, Jacksonville is known for its Victorian-era architecture and preserved downtown, making it a living history experience. Boutique inns and cozy bed-and-breakfasts offer modern amenities within beautifully restored spaces.

History buffs can explore landmarks like the Beekman Bank Museum or hop aboard narrated trolley tours to experience the Gold Rush stories that shaped the town. Simply strolling the historic streets creates a connection between past and present.

Jacksonville’s dining scene reflects this balance as well—both rooted in tradition and embracing global flavors. Start the morning with a handcrafted coffee and pastry, linger over a casual lunch, or treat yourself to a refined evening meal featuring seasonal Pacific

Northwest ingredients paired with local wines. From casual bites to refined Pacific Northwest dining, Jacksonville celebrates the region’s culinary richness.

Always Something To Do

Downtown Jacksonville is a paradise for shoppers. Independent boutiques, artisan galleries, and specialty shops line the historic streets, offering everything from hand-crafted goods to carefully curated fashion, books, and home décor. Local galleries showcase the work of Southern Oregon artists, while artisan spaces invite visitors to explore creativity themselves. Whether picking up a souvenir or treating yourself, the retail scene perfectly complements the town’s food and wine offerings.

Beyond the shops and galleries, Jacksonville brims with activity year-round. Autumn brings spectacular fall foliage across vineyards and trails, while mild weather allows for outdoor adventure in every season. Visitors enjoy hiking in the Jacksonville Woodlands, rafting on the Rogue River, paddleboarding at Applegate Lake, or simply strolling through vineyards.

Music is also at the heart of the community. The world-renowned Britt Music & Arts Festival draws performers and audiences from around the globe, while local venues and wineries host intimate performances that ensure there’s always a soundtrack to your stay.

Plan Your Visit

Jacksonville isn’t just a destination—it’s an experience, and easy to see why travelers from across the country are discovering this gem. Whether it’s wine-tasting by trolley, shopping along Victorian streets, exploring the outdoors, or sampling seasonal dishes, Jacksonville offers the perfect combination of flavor, history, and hospitality in the heart of Southern Oregon wine country. Come Visit Jacksonville!