See Shakespeare and Much More in Ashland, Oregon

Ashland, Oregon, is the ultimate weekend destination. The problem is that when the weekend is over, you don’t want to leave. Close to the western border of Oregon and California, Ashland is nestled in scenic Rogue Valley, which offers an exhilarating mix of culture, cuisine and natural beauty. From wineries and farmers’ markets to hiking and rafting there’s plenty to do, but the proverbial cherry on this laid-back, arts-centric community is the Oregon Shakespeare Festival with productions from February through October.

Founded by Angus Bowmer in 1935, the nationally renowned Oregon Shakespeare Festival presents up to 11 plays a season. There are always two Shakespearean plays on the bill but also an eclectic mix of classics, musicals, world-premiere plays and commissioned programs that include “American Revolutions: The United States History Cycle.” The several venues include the enchanting outdoor Allen Elizabethan Theatre that is similar to London’s Globe.

Allen Elizabethan Theatre
The Allen Elizabethan Theatre in Ashland is home to the Oregon Shakespeare Festival. Photo courtesy of Jenny Graham.

Ashland is a picturesque, walkable town with all the boutique shopping, craft beers, espresso drinks, wine bars, ethnic, trendy, vegan and gourmet eateries anyone might crave. The Lithia Artisans Market runs every weekend from April to November, and there are seasonable foodie events — even one for chocolate. The home of Southern Oregon University, Ashland’s the hub of health- and earth-conscious folks who take “organic” to new heights. The Food Co-Op market even has bulk-food scoops labeled “organic” and “non-organic.”

Friendly to both families and pets, Ashland offers green spaces and playgrounds, including the magical Lithia Park located in the heart of the city. Miles of foot trails follow a brook, and “creek walking” is a thing. The exhibits and innovation lab at Science Works Hands-On Museum rival those found in much larger cities and are perfect for a rainy day.

Crater Lake — a spectacular national park — is an easy day trip 90 miles northeast. The pristine lake — the deepest in the United States — was formed by a now-collapsed volcano, and the Rim Drive offers views of the cinder-cone island and other formations. Nearby Mount Ashland has a community-owned ski area where children and seniors ski for free.

Mount Ashland towers above scenic Ashland, Oregon. Photo courtesy of Ashland Travel Guide.

The Rogue Valley loves to celebrate holidays. There’s a huge turnout for the Children’s Halloween Parade, where everyone in costume is considered a child for the day. April features the Ashland Film Festival and the Britt Festival, the Pacific Northwest’s premier outdoor performing arts festival, which takes place from June to September.

Many visitors drive north from San Francisco or south from Seattle or Portland; others fly to Medford, only 12 miles away. The Rogue Valley Airport has frequent connections to all major Western cities, making it either a non- or one-stop trip from anywhere in the U.S. First-time travelers may be surprised to be greeted in the gate area by displays advertising cannabis. Oregon has been a pioneer in legalizing marijuana, and it’s a major crop of the aptly named Rogue Valley, along with flourishing vineyards and orchards. Medford is the home of the Harry and David mail-order company, which also offers a large retail store and factory tours.

Along with a few motels and one historic hotel, bed-and-breakfast inns provide most of the downtown lodgings in quaint cottages and Victorian homes. The best Airbnbs are more rural but only 10 minutes from the center of Ashland. Our favorites are in Talent, a hamlet halfway between Ashland and Medford.

Zenith Farm, with a rotating herd of llamas, sheep and horses, is perched on a hill with breathtaking valley views and spectacular sunsets and offers three accommodations. The Shakespeare Suite, which sleeps five, echoes a Tuscan farmhouse with a working fireplace and private terrace. The Zen Hideaway Loft sleeps seven and has two bedrooms and a huge deck. The most unique offering is a classic Airstream reimagined by talented craftsmen into an artsy tiny home that sleeps three.

Zenith Farm in Talent, Oregon.
A gate leads to Zenith Farm, an Airbnb location in Talent, Oregon. Photo courtesy of Giulia Longo.

Within walking distance of downtown Talent, Shady Grove Farm offers travelers with horses an arena, pasture and quality hay from the farm. The property is a sanctuary for rescued abused and neglected animals. Their Garden Cottage sleeps four with a huge kitchen and a fenced yard, the Studio next to the wildlife pond sleeps three, and the Bunkalo makes “glamping” luxurious with electricity and an outdoor bathhouse. For more pampering they sometimes offer a suite inside their home. Both gated farms have delightful hosts and are pet-friendly.

Wine treks are part of the scene, and it could take several weeks to see them all. You can join a tour, but if you plot your own course, put Cowhorn and Weisinger at the top of your list.

Ethnic restaurants abound, and if they don’t sell organic, locally sourced foods they won’t stay in business in this “crunchy” community for long. One standout is Smithfields in the center of town. Named after the London meat market, it unabashedly serves choice cuts of farm-fresh meats with distinctive plates for veggie-lovers. New Sammy’s Cowboy restaurant in Talent is a destination in itself, but it’s only open four days a week, so plan accordingly for one of the best meals of your life.


Farm stays: Zenith Farm,; Shady Grove Farm,

Restaurants: Smithfields,; New Sammy’s Cowboy Bistro,

Oregon Shakespeare Festival:

Britt Festival:

Ashland Film Festival:

Oregon Chocolate Festival:


Cannabis dispensary: