Not long ago, I took a weekend trip down to Ashland, Oregon. They’re famous for hosting the Oregon Shakespeare Festival (OSF), and I’ve been a major Renaissance geek almost since birth. (I even chose my university based largely on the fact that they hosted one of the largest Shakespeare festivals in the country.) So, I lured the husband under false pretenses, threw the dogs in the backseat, and headed south! Turns out, it’s just about the most perfect weekend getaway imaginable. ashland oregon travel guide

{Pics from the road: Digging my pedicure? / Haaaaaaay. / Gratuitious puppy photos /
Gorgeous shops downtown / Shakespeare Festival goodness}

Ashland – an easy day’s drive from Seattle, Portland or San Francisco – is a charmer of a town. The whole city just seems to conspire to give you the best, most relaxed vacation you’ve ever had. The shops are quaint, the people are friendly, the food is good…it’s hard not to love. And the crown jewel in all that wonderful? The Oregon Shakespeare Festival. We saw a production of As You Like It, and I was awestruck. The sets were unbelievable, and the acting was some of the best Shakespeare I’ve seen anywhere. Even the husband liked it! I can’t wait to go back next year and see a full weekend of shows.

If you go:

The Basics: Ashland is in southern Oregon, right off I-5. It’s an 8-hour road trip from San Francisco, 7 from Seattle or a quick 4 hours from Portland. Once you’re there, you’re a hop and a skip from Crater Lake, Klamath Falls and all sorts of other natural wonders…as well as the Rogue Creamery, which is key if you’re a cheese fiend like me.

Stay: I’m partial to the Best Western Windsor Inn. No, it’s not the fanciest spot in town, but I’m a sucker for a theme vacation, and it’s decorated like a Tudor mansion. Their service is always wonderful, they take pets, and they have a pool. But if it’s luxe you’re after, you want the Ashland Springs Inn, which is gorgeous and right downtown.

Do: Try to see at least two plays…and make sure at least one (if not both) are in the open-air Elizabethan theater (in that photo above) – it’s an incredible experience to watch Shakespeare under the stars! I always prefer the traditional shows over the modern interpretations, but pick what you love. {I’ll also add that the OSF box office people are beyond wonderful if you need help choosing. In fact, one of them even watched my dogs while I saw the show!}

Get your shop on: Shopping is actually pretty great in Ashland – lots of awesome vintage clothing, even more wonderful book shops (specializing in Tudor lit, of course), and a couple of surprises, including a shop called Prize which was so lovely it deserves its own post. Too bad they wouldn’t let me take photos of the interior. Packed with beautiful fine and costume jewelry from some of my all-time favorite designers, home accessories, gifts and old-fashioned candy, this store was singing my song in a big way.

Eat: If I’m honest, I don’t go to Ashland for the food. It’s good, don’t get me wrong, but nothing’s ever blown my socks off. That said, one of my great pleasures in life is the boiled egg breakfast at Cafe 116 (which also has Blue Bottle coffee!). Finding a soft-boiled egg is nearly impossible these days, and this one comes to you perfectly cooked to order, in one of those cute little egg cups, and is served with toast and fresh jam.

If you’re in need of a last-minute Labor Day escape, give this one some serious thought. Happy trails!

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