Ashland, Oregon Travel Guide: Shakespeare, Gardens & Gluten-Free Gold

Curtain time at the Oregon Shakespeare Festival.

Ashland, Oregon is a town of about 21,000 people where the main employer is, essentially, Shakespeare.

Sit with that. A whole functioning small-town economy — hotels, restaurants, bookstores, a downtown that hums past dinner — built around a repertory theatre festival. Ashland is the small town where artists, actors, and creatives actually make a good living with their art, and you can feel it in every storefront: the whole downtown is artsy in a lived-in way, not a gift-shop way.

We spent three days here on our Oregon road trip. Here’s the full guide.

Where to Stay in Ashland

We stayed at the Swank Suites at Swank House, and I highly recommend it: high-design suites in a restored historic house, within walking distance of everything — the theatres, Main Street, Lithia Park, dinner. In a town this walkable, staying central is the entire game, and Swank House plays it perfectly. (Google Maps)

The Oregon Shakespeare Festival: Book the Outdoor Theatre

The Oregon Shakespeare Festival is the reason to time your trip. Our formula, which I’d repeat exactly: three days in town, two nights of shows, and a slow walk downtown for a bite before each curtain.

One thing we didn’t do that you absolutely should: book at least one show at the Allen Elizabethan Theatre — the open-air stage patterned on a 1599 London playhouse. Shakespeare under the stars in an Elizabethan-style theatre is the postcard Ashland experience, and tickets go fast. We caught a musical indoors instead (zero regrets, see below), but the outdoor stage is the one I’m coming back for.

Come From Away, moments before it emotionally destroyed the room.

Things to Do in Ashland, Oregon (Besides the Theatre)

• Lithia Park — 93 acres of gardens and forested canyon along Ashland Creek, designed by John McLaren, the same landscape architect behind San Francisco’s Golden Gate Park. We wandered the gardens and did a little hike up the canyon; it starts a block off the Plaza. (Google Maps)
• Bookstore-hop downtown — there are SO many bookstores for a town this size. Budget a suitcase pound or two.
• Do something silly — we won a Wild West escape room downtown, and the photographic evidence of us in cowboy hats holding prop gold will outlive us both.
• Creekside dinner + live music — the row of restaurants along Ashland Creek behind the Plaza is the pre-show move, and the town has real nightlife and live music for its size.

The heist was successful. The hats were mandatory (they were not mandatory).

Where to Eat in Ashland (a Gluten-Free Paradise, Somehow)

I did not expect a town of 21,000 to out-gluten-free San Francisco, and yet: Ashland is loaded with gluten-free-friendly restaurants.

• Zi Spice — the runaway winner. Farm-to-table, chai lattes with A2 milk, and a gluten-free sourdough so good I demanded a recount. I wrote a full Zi Spice review because it earned one. (Google Maps)
• Blue Toba — Indonesian food downtown, and the noodles are great. We went for dinner and left plotting a return. (Google Maps)
• Greenleaf — our creekside meal by the Plaza; exactly the setting you want before a show. (Google Maps)

When to Visit Ashland (Read This Part)

Summer is beautiful, and the Shakespeare Festival season is peak Ashland — go then if you can. One honest caveat: southern Oregon has a real fire season. During one recent bad stretch, this area recorded some of the worst air quality in the country. If you’re visiting outside festival season, check air quality before you commit the trip.

Ashland was one stop on our Oregon road trip — my Portland travel guide covers the northern leg, and the rest of my travel guides go considerably farther afield.

This is part of my travel series — I spent five years reviewing places around the world as a digital nomad (all the guides live here), and now I road-trip out from San Francisco with the same notebook. Subscribe to my newsletter for new guides and reviews — and if you’re a writer who wants a career that travels this well, that’s what Make Writing Your Job is for.