Ashland, Oregon is the ultimate weekend destination—the problem is that you never 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 farmer’s 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.

Allen Elizabethan Theater

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 including American Revolutions: The United States History Cycle.  There are several venues including the enchanting outdoor Elizabethan Theater, similar to London’s Globe.

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.”

Family-and-pet friendly Ashland offers green spaces and playgrounds including the magical Lithia Park located in the heart of the city.  Miles of foot trails follow the babbling brook and “creek walking” is a thing.  The exhibits and innovation lab at Science Works Hands-On Museum rivals those found in much larger cities and is 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 the now-collapsed volcano and the Rim Drive offers views of the cinder cone island and other formations.  Nearby Mt. Ashland has a community-owned ski area where children and seniors ski for free!

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.

Celebrating Halloween in Ashland.

Many visitors drive north from San Francisco or south from Seattle or Portland; others fly to Medford, only 12 miles away to the Rogue Valley Airport with frequent connections to all major western cities making it either a non or one-stop trip from anywhere in the US.  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 with a large retail store and factory tours.

Zenith Farm, located between Ashland and Medford

Along with a few motels and one historic hotel, most of the downtown lodgings are in B & Bs in quaint cottages and Victorian homes.  The best Airbnbs are more rural, but only 10 minutes to 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.  Superhosts Giulia and Josh offer three exquisitely clean accommodations.  The Shakespeare Suite (sleeps 5) echoes a Tuscan farmhouse with a working fireplace and private terrace.   The Zen Hideaway Loft (sleeps 7) has two bedrooms and a huge deck.  Their most unique offering is a classic Airstream revisioned by talented craftsmen into an artsy tiny home (sleeps 3).

Shady Grove Farm

Within walking distance of downtown Talent, Shady Grove Farm offers travelers with horses an arena, pasture and quality hay from the farm!  Lin and Lynn’s property is a sanctuary for rescued abused and neglected animals. Their Garden Cottage (sleeps 4) with a huge kitchen and a fenced yard; the Studio next to the wildlife pond (sleeps 3), and the Bunkalo makes “glamping” luxurious with electricity and an outdoor bathhouse.  For more pampering they sometimes offer a bed-and-breakfast 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 Weisingers 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 Smithfield’s 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.

Rogue Valley Oregon, courtesy of sou.ed

So many visitors fall in love with the Rogue Valley that real estate is booming.  Just be sure never to mix up the organic and non-organic scoops at the market!

About the Author:

Gay Courter is a bestselling novelist (The Midwife, Code Ezra, Flowers in the Blood) and documentary filmmaker.  She travels for both work and pleasure since her first around-the-world trip at age six.