8.9 out of 10


42.1897527432089 -122.704114794743
Great for
  • Clean & Green
  • Eating Out
  • Neighborly Spirit
  • Parks & Recreation
  • Safe & Sound
Not great for
  • Cost of Living
Who lives here?
  • Families with kids
  • Retirees
  • Tourists
  • LGBT+
  • Country Lovers


5/5 rating details
  • Neighborly Spirit 5/5
  • Safe & Sound 5/5
  • Clean & Green 5/5
  • Pest Free 1/5
  • Peace & Quiet 4/5
  • Eating Out 5/5
  • Nightlife 5/5
  • Parks & Recreation 5/5
  • Shopping Options 5/5
  • Gym & Fitness 4/5
  • Internet Access 4/5
  • Lack of Traffic 4/5
  • Parking 4/5
  • Cost of Living 2/5
  • Resale or Rental Value 4/5
  • Public Transport 3/5
  • Medical Facilities 4/5
  • Schools 5/5
  • Childcare 3/5
Editors Choice

"Stratford Upon Oregon"

Way back when I was in my senior year of high school, I had a little adventure in Ashland. I was a bit of arty kid in the making, so I found out that there was this Shakespeare festival here in Ashland and decided that I would come and see it. Now, for whatever reason, I didn’t really have anyone to go with me so came up alone. Right from the beginning things were funny about that trip. This was back when I lived in Southern California. I got a Greyhound from the North Hollywood station. I checked my bags in and then stood around waiting for the time to go. I remember this guy came into the station and never took a seat. He was very fidgety, pacing back and forth and looking out the window. I just figured that he was one of those nervous types.

Then just as he had come to a stop right next to me, I suddenly saw a foursome of cops come running in, guns drawn, and pointing (for a second I thought it was at me) at the guy right next to me, who they quickly subdued while another set of cops emptied us from the station and put us on the bus. I never found out what was going on with the whole thing, though somebody said they thought the guy had a bomb.

Regardless, they sent us off without our bags. I would never get my clothes back until the day I came back. Luckily, I had my money and wallet with me already and both my lodgings and tickets were already bought and paid for and waiting for me in Ashland.

Ashland is an amazing little city. Not too far north of the California border and about 10 miles south of Medford, Ashland thrives off its Shakespeare festival. Where I live now, in Orinda, there is also a summer Shakespeare festival—Cal Shakes—but our little festival looks like Romper Room compared to what they have going on in Ashland with its multiple theaters and diverse productions (they don’t just do Shakespeare). I have been to a few different West Coast Shakespeare festivals and the one in Oregon is definitely the gold standard of West Coast festivals. (This is not to say they have the best dramatic program on the West Coast, only that their Shakespeare productions are the best.)

Ashland has the feel of a Colorado Rockies sort of town. It is very green and leafy and you definitely feel as if you are well removed from any kind of urban problems. The town obviously grew up off Highway 5, what in California is called the Golden State Freeway, but must surely have a different name once you cross the border. It is the same highway that you can take all the way from Tijuana to Port Angeles, Washington. (I don’t know if when you fairy into Canada it continues there as well.)

They have really cashed in on the Shakespeare Festival as well. There are a number of hotels and quaint restaurants where the actors go after plays. I remember going to one—the Black Sheep Pub, maybe?-- and sitting just close enough to overhear the actors from Cyrano (without the nose but still with leftover make up) drinking it up and reveling in the excitement they got from a good night of live theater. Many of the locals have also converted their lives to make money off the possibilities. This was the case with the bed and breakfast in which I stayed. The woman who ran it—an ex-school teacher—had converted her grown kids’ former rooms into individual rentals. She was awfully nice and took a mother hen sort of attitude towards me once she heard of my “harrowing” trip up.

But really, most everyone in the town was really nice. Even as I wandered about town by myself taking in the plays at night and hanging around town in the day, there seemed to always be someone to talk to. It reminded me most of the town from the Steve Martin film Roxanne (ironically, also based on Cyrano de Bergerac).

Southern Oregon College is at the end of town. It seemed like little more than a community college to me, but I remember that I met one of the students there and after she got over having this high school kid trying to strike up a conversation with her, I remember that we had an animated discussion about whether it was more important to have intensity of emotion or clarity of mind for artistic creation (I argued the former). She was a Photography or Graphic Design major as I remember.

A lot of the rest of the time I spent at the parks in town, which are really great. One of them, has some kind of fancy water works, I think. When the high school kids get off school, a lot of them hang out at these parks in the quaint “downtown” area. When I was there, I met this girl named Autumn P. and we ended up going out one night. (She drove her mother’s car after her mother called the Bed and Breakfast owner to make sure I was who I said I was. That’s the kind of small town atmosphere they have there, everyone knows everyone else.) I still remember how fun it was hanging out with this complete stranger and getting an insight into what it would be like living in a small, kind of hippy-dippy/artsy town like this.

There are some surprising things about Ashland. For example, given the quaintness of the town, you might expect people here to be extremely well-off, but actually the median income here is only $40K. Even with lower costs of living in Oregon, this is really surprising. My only explanation for this is that the students from the local college bring this amount down. It is certainly not because of local high school, which gets the highest ratings around. It is also not because of the crime rate which is consistently lower than the national average.

Overall, this is would be a great little town to live in. I would certainly not mind living here.
  • Shakespeare Festival
  • Quiant Colorado Town Feel
  • Excellent Schools
  • A Bit Out of the Way
  • Tourists Must Get Old
  • Everyone Knows Everyone
Recommended for
  • Families with kids
  • Retirees
  • Tourists
  • LGBT+
  • Country Lovers

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42.1898964854198 -122.715920905576

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