By Julie Snyder

What’s not to like about Ashland? Nestled in a mountain valley halfway between San Francisco and Portland, the southern Oregon community is a mecca of culture and cuisine, a launching pad for winter and summer recreation, and a cradle of small-town charm.

The 1850s mill town once provided flour and lumber for gold-hungry settlers in nearby Jacksonville. In modern times, Ashland has mined its own gold as an internationally renowned destination. A population of just over 20,000 permanent residents swells seasonally as visitors flock in to partake of the region’s many pleasures.

From March through October, the play’s the thing as the Oregon Shakespeare Festival (OSF), the nation’s oldest and largest nonprofit repertory theater company, stages its magic. Which makes it the perfect annual rendezvous spot for my friend Ellen and me, theater-lovers both. Ashland is nearly equidistant between our respective homes in Oakland, California and Portland, Oregon. A bonus: she’s an OSF member which means first dibs on dates and seats.

In the five years since Ellen and I launched this tradition, we’ve developed a comfortable routine. We stay in the same room at the Bayberry Inn, a lovely bed & breakfast that’s just a 10-minute walk to downtown and the theaters. We see one Shakespeare production and one other play, typically choosing matinees. This year it was a gender-bending As You Like It and an energetic production of Hairspray that had us all dancing in the aisles and singing “You Can’t Stop the Beat.”

And we eat. Always on the menu: fabulous, filling breakfasts at our inn and leisurely dinners at one of Ashland’s wealth of restaurants. This year we sampled sushi at Sakana, a stylish new Japanese pub. Another night, we joined our charming rosy-cheeked innkeeper, Francesca, at Amuse, and shared tasty small bites, including charcoal-grilled prawns, silky-sauced gnocchi, and warm beignets.

Our days begin with a walk in the hills before breakfast for eclectic architecture, flowering gardens, and deer encounters. In the Downtown Historic District (on the National Register of Historic Places), we check in at our favorite bookstores, Bloomsbury Books and the Book Exchange, and browse the wares at Paris Green and Travel Essentials. We always say we need nothing but somehow end up willingly supporting the local economy.

Ashland’s romance with the Bard dates to 1935 when Angus L. Bowmer was inspired to stage Shakespearean plays outdoors in Ashland’s Lithia Park. A crew funded through the Works Progress Administration (WPA) helped build a stage, with an Elizabethan façade. The Merchant of Venice and Twelfth Night were performed that first season. 

Today’s opulent outdoor theater was built in 1959, after a fire and then flimsy construction claimed the first two efforts. There’s nothing quite like watching Shakespeare’s vivacious verse come alive in spirited performances under the stars on a balmy summer evening.

During Angus Bowmer’s 40-year tenure as artistic director, he produced all 37 of Shakespeare‘s plays and performed in 43 separate stagings. Today, performances are held in the 1,190-seat, outdoor Allen Elizabethan Theatre as well as three smaller indoor venues, the Angus Bowmer, Thomas, and Mountain Avenue Theatres.

If you hope to broaden your theatergoing beyond the Bard, fear not. Every OSF season also offers an eclectic collection of classic and contemporary productions.

Behind the scenes, OSF and its 600-person staff have been on a bit of a rollercoaster. The first new artistic director in 12 years (the organization has had just six) joined the organization this year and a search is on for a new executive director. The challenges of filling seats and operational coffers are perennial. A contract for the stage crew union, chartered in 2016, expires in November.

Unfortunately, in recent years Mother Nature has assumed a leading role with raging wildfires that have transformed wilderness not far from Ashland into ash lands. The resulting smoke has forced cancellation of outdoor productions, as well as disrupting other fresh-air pursuits.

In the front of the house, however, the show must go on and theatergoers like Ellen and I savor the performances of an exceptionally talented troupe of actors. We’ve already reserved tentative dates for next year.

In addition to OSF, Ashland’s culture club boasts Ashland Contemporary Theatre, Rogue Valley Symphony, and the Oregon Cabaret Theatre. Over the Christmas holidays, the Festival of Light illuminates the historic architecture along Main Street with over 1 million lights.

On weekends from March through October, the Lithia Artisans Market sets up shop downtown along Ashland Creek at the foot of Lithia Park. Browsers can shop the juried arts and crafts of 40 artists and dine at one of the neighboring cafes with a background of live music.

For foodies, Ashland serves up a tasty menu of culinary events: Oregon Chocolate Festival in March; A Taste of Ashland in April; and the Ashland Culinary Festival in November. And the wine tasting is divine, with more than 70 grape varieties grown in Southern Oregon. Visitors can organize their own tour with maps from Travel Southern Oregon or join a guided wine tour. If beer is the beverage of choice, one can check out Caldera or Standing Stone brewing companies.

Those with a taste for outdoor adventure need look no further than Ashland’s Lithia Park. Designed by John MacClaren, landscape architect for San Francisco’s Golden Gate Park, the 93 acres of manicured grounds and sycamore groves border downtown, steps away from the theaters. Visitors meander to the Japanese garden and lounge next to duck-dotted ponds. And they head into the hills on trails and fire roads for hiking and biking. Nearby Mt. Ashland Ski Area features four lifts and the spectacular Siskiyou Mountains scenery.

Further afield but still close enough to make Ashland home base, the Rogue River offers rafting thrills, while Crater Lake, the deepest lake in the U.S., dazzles from vista points around its 33-mile rim.

But for Ellen and me, it’s mostly about Shakespeare and friendship. And for these, Ashland truly is the perfect rendezvous, Bard-none.

Julie Snyder lives in Portland, Oregon. As a writer, editor and publisher, she’s contributed to a variety of lifestyle, in-flight and travel publications, and produced award-winning catalogs for Backroads travel company. Among her passions are animal welfare, walking, travel, and the Green Bay Packers.