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Ashland, Oregon, has always been something of an enigma to me. There’s no major industry, no seaport, no international airport and the population is only about 20,000 people.

osf banner

I’ve listened intently when friends told of their visits to this secluded little town. The big draw was always the Oregon Shakespeare Festival — but still? My curiosity finally got the best of me and I had to find out more about this laid-back woodsy community located just 15 miles north of the California border.

The scenery is beautiful, with lush green forests and rolling hills nestled at the foot of the Siskiyou and the Cascade mountain ranges, all served up in a mild, smog-free, four-season climate.

ashland street scene

On the streets of Ashland, Ore.

The streets of Ashland are dotted with unique little shops and eateries and festooned with banners and flowers that celebrate the Oregon Shakespeare Festival, known as the OSF. It was interesting to walk around town and observe the other folks doing the same. They were generally dressed comfortably in shorts and sandals, or sneakers, with smiles on their faces.

I noticed a high percentage of young adults, undoubtedly students at nearby Southern Oregon University. And there was a Bohemian culture replete with artsy types, tie-dyed shirts, long hair and tattoos. It’s a pretty eclectic, but very friendly, population. There also were a lot of senior citizens, obviously retired.

Ashland has been consistently ranked as one of the best places in the U.S. to retire. I dropped in on some old friends who retired there 25 years ago and asked them about their favorite local attractions. They gushed on and on about the virtues of Ashland, local wineries and the OSF. Perhaps if they were younger they would have told me a little about the extensive outdoor activities too.

emigrant lake

Because of the close proximity to the Rogue River and Emigrant Lake, there’s plenty of water sports. Summers offer swimming, white-water rafting, kayaking and hiking. In winter there’s skiing, snowboarding and sledding. For the truly athletic, there’s serious competitive-running and year-round bicycling events. For the sedentary, how about golf and fishing? Something for everybody.

Tourism draws about 300,000 people a year and in spite of all there is to do in Ashland, the main event is still the Oregon Shakespeare Festival, which claims about 1/3 of the visitors every year. The locals are all wild about the OSF.

Green stage setup

The OSF complex consists of three main theatres, the Angus Bowmer Theatre, the Thomas Theatre and the Allen Elizabethan Theatre. The name “Allen” was recently added to this huge outdoor theatre — justifiably so — as a thank you for a large donation from Paul G. Allen, co-founder of Microsoft.

Green Show performance

The Green Show

On the patio outside of the theatres there’s a free show most evenings where music lovers sit on the lawn to watch local talent perform their hearts out. It’s called the Green Show and I truly enjoyed the performance, but my postage-stamp-sized place on the lawn was pretty cramped. I was grateful when it was time to go into the Allen Elizabethan Theatre to watch the headline performance of “The Wiz.” 

Wiz backdrop

Admittedly, The Wiz is not Shakespeare, but it’s in keeping with the annual OSF tradition of presenting plays by Shakespeare, along with other classic and contemporary productions. Their season runs from mid-February through October and, including all three theatres, features 11 shows each year.

If you’re not ready to go to Ashland yet, here are a few more points to consider: cheap gas and legal cannabis — and, how’s this? There’s no sales tax in Oregon. Maybe that’s why so many people retire there!

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