Ashland Offers Arts, Culture and the Great Outdoors in Oregon

Ashland is considered the cultural capital of southern Oregon. Its diverse wine region, sophisticated restaurants and thriving arts scene compares to the Napa Valley, though it maintains a distinctive personality all its own. Renaissance-inspired bars, charming galleries and an array of scenic hikes are just a few of this small town’s draws.

Whether you visit for the Oregon Shakespeare Festival at the Allen Elizabethan Theatre or to explore up-and-coming breweries, Ashland’s infinite appeal caters to a diverse crowd, making it one an easy choice for a weekend or weeklong getaway.

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Lithia Park, Ashland, Oregon

Nature’s Paradise

It’s no secret that Ashland is an outdoor junkie’s haven. With the 100-acre Lithia Park right in its backyard, visitors can hike along Ashland Creek and explore stretches of forested canyonlands without leaving the city. Home to century-old landmarks, a Japanese garden, tennis courts and several ponds, the park offers an array of activities and places to explore.

Lewis Carroll lovers can bike or hike part of the Ashland Watershed Trail system dubbed “The Alice in Wonderland Trail,” a short, single-track route that connects to Lithia Park. Siskiyou Mountain Park is another option for those who want to stay relatively close to town, with 300 acres that appeal to hikers, mountain bikers and horseback riders alike.

For a more strenuous experience, head south of town and hike a stretch of the Pacific Crest Trail to Mount Ashland Meadows, a prime area for viewing wildflowers in the summer. Just east of the city, Grizzly Peak is another popular spot for hikers, offering sweeping views of the surrounding Rogue Valley.

ashland schneider museum
Schneider Museum of Art, Ashland, Oregon

Thriving Arts Scene

It was the Tony Award-winning Oregon Shakespeare Festival that really put Ashland on the map, and it remains a popular attraction to this day. Founded in 1935, the annual festival is one of the oldest and largest nonprofit theaters in the country, offering more than 750 performances over the course of eight months each year.

Visitors are encouraged not only to attend a show, but to also participate in one of the backstage tours. If theater isn’t your cup of tea, Ashland’s historic Downtown District and Railroad District are both full of local art galleries and studios. Art aficionados are encouraged to stop by the Schneider Museum of Art, a free, year-round display of exhibits by local and internationally renowned artists.

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Caldera Brewing, Ashland, Oregon

Eat and Enjoy

With more than 100 restaurants to serve a population of about 21,000, Ashland’s culinary scene is no slouch. For a true taste of the town, visit Oberon’s, a Shakespeare-themed pub with staff in Renaissance garb that offers live music and mead on tap. The restaurant also maintains an eclectic whiskey collection and hosts weekly tastings (but make sure not to mix alcohol and driving).

Larks Home Kitchen Cuisine is an option for those looking for upscale, farm-to-table fare. Known for its diversity of grapes, southern Oregon’s vineyards are starting to gain recognition from oenophiles around the country. For a tour of some of the best wineries in the area, visitors can pick up a Bear Creek Wine Trail passport.

The trail encompasses 14 wineries and nearly 40 wines, covering the southernmost portion of the Rogue Valley American Viticultural Area. The Bear Creek Wine Trail offers a list of drivers for hire to tour the trail responsibly. Exploring Ashland’s many breweries and craft cocktail bars is another common pastime. Alchemy Restaurant and Bar and Brickroom complement their impressive cocktail menus with both casual American fare.

Beer snobs should swing by Caldera Brewing, an Ashland favorite and the first craft brewery on the West Coast to start canning beer. Standing Stone Brewing Co. is another family-owned, distinctly local brewpub that’s worth checking out. Again, remember to schedule a safe ride home when alcohol is involved.

–Written by Maggy Lehmicke, last updated in October 2021.

Interested in planning your next road trip with AAA Washington? Call your travel agent directly or your nearest AAA store to get pro tips, TripTik maps, and more. Find more Pacific Northwest scenic drives and road trips.

  • From Seattle: About 458 miles
  • From Spokane​: About 565 miles
Best For
  • Shakespeare theaters
  • Outdoor adventures
  • Gallery hopping
  • Wine tasting
  • Exploring local breweries
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