Explore Ashland, a mountain town with a rich culture

By Greg Johnson

Ashland’s picturesque setting at the base of the Siskiyou and Cascade Mountain ranges complements the town’s reputation as a cultural hot spot for live theater, art, dining and award-winning wineries.

Most visitors may associate this eclectic city located off Interstate 5 south of Medford with the world-famous Oregon Shakespeare Festival, while Southern Oregon University in Ashland is known for its focus on environmental stewardship, critical thinking and career preparation.

But there’s much more to explore in Ashland. The town of 21,000 residents boast amazing wineries, culinary delights, recreation and of course, theatrical productions. In fact, Ashland was named among the top best small towns in USA by USA Today’s 10 Best Readers Choice travel awards in 2023. The Oregon Shakespeare Festival will present nine productions this year in its three theaters, which include the 1,190-seat open-air Allen Elizabethan Theatre, the 600-seat Angus Bowmer Theatre and 360-seat Thomas Theatre.

The season’s offerings include William Shakespeare’s “Julius Caesar” as well as reimagined and adapted classics, an August Wilson play and a production of “Into the Woods” with music and lyrics by Stephen Sondheim. The season started in March and runs through Oct. 26.

The city’s vibrant visual art community reveals itself in numerous galleries. Influences range from fine-art prints, sculptures and hand-blown glass to Native American art, pottery, jewelry and handcrafted furniture.

The Schneider Museum on the Southern Oregon University campus displays contemporary visual arts exhibits from around the country. The museum and most of the major galleries are located within walking distance from Ashland’s historic railroad district to the university campus. 

Ashland boasts an array of affordable dining options as well as fine dining. For a unique experience, Caldera Brewing & Restaurant offers 45 beers on tap. Diners can also enjoy delicious pub fare, ales, lagers, seltzers and sodas. Another great option is the open-air hangout Skout Taphouse & Provisions, located across the street from beautiful Lithia Park in downtown Ashland. The dog-friendly creekside pub offers tasty fare, beer, cider and cocktails. On the fine dining side, Alchemy Restaurant & Bar and Chateaubriand36 steakhouse are standouts.

There are several wineries in the fertile Southern Oregon wine-growing region around Ashland. Wine tasting is offered at many of the wineries including Del Rio Vineyards, Irvine & Roberts, Weisinger Family Winery, Dan Campbell Winery and Dancin Vineyards. Visitors will also enjoy the Mediterranean chateau at Belle Fiore Winery, which is surrounded by 31 acres of wine grapes producing classic vintages.

Those exploring Ashland in the spring can see a parade of cherry blossoms while strolling through a mile-long nature walk in the 100-acre Lithia Park, the city’s crown jewel. In summer, they can take a guided 1½-hour nature walk along paved trails through the gardens. The area is lined with trendy cafes and shops and the grounds of the Oregon Shakespeare Festival. Note: No dogs are allowed in the park.

Outdoor enthusiasts will find plenty of recreational opportunities. Fishermen can cast a line in the famed Rogue River for hefty salmon, steelhead and trout. Hikers enjoy trekking the twists and turns of the White Rabbit Trail, Cheshire Cat Loop, Red Queen trail and other trails in the network known as the Alice in Wonderland Trail System (officially called the East Side Forest Lands.) Another hiking option is Upper and Lower Table Rock trails, which wind through wildflower meadows and forests. The hike leads up to clifftops with panoramic views of the Rogue River Valley.

Ashland’s lodging options include the unique Lithia Springs Resort and Ashland Hills Hotel and Suites, a great place for dog owners who appreciate walking their four-leggers on the 14-acre property.

For information:

• Travel Oregon, Traveloregon.com

• Travel Ashland, travelashland.com

• Oregon Shakespeare Festival,

osfashland.org

• Caldera Brewing & Restaurant,

calderabrewing.com

• Skout Taphouse & Provisions,

skoutashland.com

• Belle Fiore Winery,

bellefiorewine.com

Greg Johnson is a travel writer for The Messenger.