Visit RoxyAnn Winery near Medford on an arts and wine tour in Southern Oregon.

Southern Oregon is beautiful driving country. Home to the Wild and Scenic Rogue River, the beautiful North Umpqua River, the Siskiyou Mountains and Crater Lake, its stunning natural beauty is worth the trip alone. The region is also home to a thriving arts culture and the Rogue Valley wine region, which has 19-century roots. Most of the area’s wineries are small, family-owned enterprises, where you are likely welcomed by the wine maker him or herself. For world-class arts, fine wine and a friendly welcome, explore these Southern Oregon towns.

Ashland
Start in the town of Ashland (pop. 20, 232), which presents the annual Oregon Shakespeare Festival. Staging 11 plays at three different theaters, the festival runs from February through November. The outdoor Elizabethan Stage opens in the summer. The Ashland Independent Film Festival takes place in April each year in the beautiful art deco Varsity Theatre, screening 80 films in five days. You can also browse more than 30 art galleries in town, including the Schneider Museum of Art at Southern Oregon University. If you are staying the night, check out the historic Ashland Springs Hotel or the charming Lithia Springs Resort. Charge your electric vehicle at the Ashland Electric Vehicle Charging Station.
Wineries: Near Ashland, visit Irvine Vineyards and Grizzly Peak Winery.

Medford
Southern Oregon’s largest town, Medford (pop. 75,501) retains a small-town friendliness. The Craterian Theater at the Collier Center is the town’s premier performance venue, producing everything from Broadway musicals to live plays. The Randall Theater Company offers comedy, drama and musicals. Local art galleries include Art du Jour Gallery, Rogue Gallery & Art Center and Siskiyou Artisans Gallery & Gifts.
Wineries: Near Medford, visit RoxyAnn WineryPebblestone Cellars and Ledger David Cellars.

Jacksonville
With scores of buildings on the National Register of Historic Places, downtown Jacksonville (pop. 2,807) is 19th century treasure. Take a self-guided tour of town, and visit the nearby Jacksonville Cemetery to learn about the town’s founders, many of who came for the 1851 gold rush. In summertime, enjoy the Britt Festivals, the oldest outdoor performing arts festival in the Pacific Northwest. The venue is located in a natural amphitheater among the trees at the estate of 19th century photographer Peter Britt. Dozens of world-class classical, jazz, blues, folk, bluegrass, world, pop and country music performances take place here during the season. Overnight at the elegant The Jacksonville Inn or the TouVelle House Bed & Breakfast.
Wineries: Near Jacksonville, visit South Stage Cellars, Cricket Hill Winery and DANCIN Vineyards.

Grants Pass
With the Wild and Scenic Rogue River running right through town, Grants Pass (pop. 34,646) is known as an outdoor recreation paradise, but it also has a growing arts culture. Visit the fine arts collection at the Grants Pass Museum of Art and more than a dozen art galleries in town. The annual Art Along the Rogue Street Painting and Music Festival is not to be missed in the fall. The elegant art deco Rogue Theatre is the town’s main performing arts venue, staging rock, jazz, blues and Celtic music each year. Spend the night at the Weasku Inn, a beautifully restored 1920s lodge on the banks of the Rogue River. Charge your vehicle at the Grants Pass Chamber of Commerce.
Wineries: Near Grants Pass, visit Soloro VineyardTroon Vineyard and Wooldridge Creek Winery.

Editor’s note: Check out our other Oregon’s Electric Byways Road Trips for more EV itineraries around the state.

About the Author: Eileen Garvin

Eileen Garvin is the editor of Travel Oregon’s Seasonal Features, enewsletters and annual visitor guide. When she’s not cooking up trip ideas, Oregon Dreamer profiles and outdoor adventures to write about, she’s out exploring Oregon.

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These maps and directions are for planning purposes only. You may find that construction projects, traffic, or other events may cause road conditions to differ from the map results. For travel options, weather and road conditions, visit tripcheck.com, call 511 (in Oregon only), 800.977.6368 or 503.588.2941.

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