Come for the music, stay for great food, wine and culture in this charming gold rush town.
Dreaming of live music and a picnic with friends under a sky full of stars? Get away to pictureseque Jacksonville, surrounded by rolling hills and vineyards near Ashland and Medford. In this small town, many of the 19th-century brick buildings and gracious homes have been preserved, and the downtown district, with its brick facades, feels like the film set of a Western. Each summer it’s home to an outdoor music festival that makes the town come alive with arts and culture.
With hiking, history tours, boutiques, top-notch restaurants and cozy lodgings, this fascinating town will coax you to stay the whole weekend — or longer. Even better, it’s a quick 15-minute drive to Rogue Valley International-Medford Airport. Here’s how to plan your trip.
Catch a Concert Under the Stars
The Britt Festival, Jacksonville’s beloved summer music festival, has been going since 1963. The venue, in the heart of town, is a natural amphitheater set among pines and madrones on the hillside estate of Peter Britt, a renowned photographer who, in the 1850s, planted some of the very first grape vines in Southern Oregon. Though within easy walking distance from many lodgings, you can also catch the free trolley from several convenient stops around town.
Running from June through September, the Britt has a show for every taste, from jazz, pop, rock and bluegrass to dance, musical theater and comedy acts. This summer’s lineup includes Alison Krauss & Union Station, Bonnie Raitt, Los Lobos & Los Lonely Boys, Pink Martini, comedian Jim Gaffigan and more.
If you time your visit for June, you can catch part of the Britt Orchestra’s three-week summer season, which will feature a mix of classical favorites from Mozart, Beethoven and Dvořák along with the film score to “The Empire Strikes Back.” Choose from reserved bench seating or spread a blanket on the grassy hillside. Be sure to bring binoculars and a picnic; you can purchase beer and wine from the on-site vendors.
Vines, Hikes and History
You don’t even have to leave town to sample the area’s renowned wines at eight outstanding wineries. Jacksonville is also the ideal headquarters for exploring the nearby Applegate Valley wine region, where warm summer days and cool nights favor varietals like merlot and chardonnay. Drive yourself — or better yet, take a trolley tour — through the picturesque wine country.
Jacksonville was once the bustling hub of Southern Oregon, and the town has seen gold strikes, destructive fires and larger-than-life characters. Learn more about Jacksonville’s fascinating history on a self-guided walking tour or trolley-driven historic Jacksonville tour. On Saturday mornings through summer, you can take a walking history tour with a knowledgeable guide in period dress. Afterward, explore the downtown boutiques — be sure to stop by Art Presence, an eclectic fine-art gallery featuring Southern Oregon artists.
For a dose of nature, check out the Jacksonville Woodlands Trail System. Several trails in this 18-mile network start right from the Britt Festival grounds. Choose a flat, easy route alongside a lush creek or a more challenging climb through sunny stands of oaks, pines and madrones.
Where to Eat and Stay
If you like your lodging with a side of history, you’ll find plenty of options in and near downtown. The McCully House Inn, built in 1860 by Jane and John McCully, is the oldest home in Oregon used as lodging. Right on California Street is the historic Jacksonville Inn, which was originally a brick mercantile warehouse.
Choose from one of five suites at Kubli Haus, a restored 1860 landmark with a wraparound porch perfect for lounging, or the Wine Country Inn, where you can charge your EV while you recharge.
Jacksonville boasts a diversity of restaurants for its small size. C St. Bistro offers fresh, eclectic cuisine and wood-fired pizzas, while the hyper-seasonal menu at Cowhorn Kitchen features Pacific Northwest ingredients paired with biodynamic wines. At Bella Union, enjoy live music along with pizza, burgers and salads on their vine-covered patio, or catch local bands and complimentary wine tastings at the Jacksonville Inn’s cozy Wine Lounge.
For more casual fare and coffee, try local favorites like Pony Espresso, with its cozy, Western-outpost vibe; and GoodBean, housed in a brick building that was once a billiard saloon.
Top photo of downtown Jacksonville by Jak Wonderly
