A Southern Oregon Foray

[Ashland, OR, Sep 4, 2026]

With my big trip to Mackinac Island, Isle Royale and Voyageurs scrapped in favor of a quick trip to Voyageurs in August, Labor Day weekend was now free. We decided to head 5 hours south to Ashland, OR.

If you haven’t heard of it, you are not alone. The town of roughly 20,000 sits just 16 miles north of the California border, in the foothills of the Siskiyou and Cascade ranges. It is best known as the home of Southern Oregon University and the Oregon Shakespeare festival. It was the latter that had brought Ashland to my attention back in the day. A friend had gifted me the book 1000 Places to See Before You Die, and Ashland’s Shakespeare festival was featured in it. What an obscure thing to include, I thought at the time. It turns out, the Oregon Shakespeare festival is nationally renowned and draws 350,000 visitors annually.

Since the drive was about 5 hours long and we anticipated having to make several stops to charge the car, we left around 8 am. Tesla chargers are sometimes near a Starbucks or a grocery store, but having a food truck nearby was a first. Curry Bai‘s proprietors arrived just as we were finishing up charging, but we decided to wait a bit longer so we can grab a chai and a snack. They were both excellent!

For lunch, we stopped at the McMenamins in Roseburg so we can get our passports stamped. McMenamins is a PNW hospitality company founded by brothers Mike and Brian McMenamin. They got their start in the restaurant and beer business in the 1980s. They championed Oregon’s landmark Brewpub Bill, which allowed breweries to sell beer directly on site where it is brewed and gave birth to the brewpub movement. After opening a second location, the brothers embarked on their first large-scale project in 1991 – converting a poor farm in Troutdale into the iconic destination resort Edgefield. Since then, the McMenamins empire has expanded to over 50 locations in the PNW, many of them salvaged historic buildings such as schools and fraternal lodges. McMenamins locations are full or original artwork and they are all quirkily decorated. I learned about the McMenamins passport soon after I started spending more time in Portland and of course, I had to get it!

We arrived in Ashland around 3 pm, just in time for check in at our downtown hotel. I checked out the wine tasting in the lobby while Ash took a nap. We then took a walk at nearby Lithia Park. The park was designed in the early 20th century by John McLaren, who also designed Golden Gate park in San Francisco. It stretches for 100 acres along Ashland creek and is named for lithia water, which was found nearby. Lithia water — naturally occurring water with elevated lithium and mineral content — was believed to have therapeutic properties, and the city briefly marketed itself as a health destination around this resource. City leaders originally envisioned a lithia water spa in the park, but the endeavor proved too expensive.

Today, Lithia park is home to several duck ponds, pickleballs courts, a Japanese garden and a rose garden. It also attracts many deer who are apparently accustomed to people! We saw a few on our walk through the park and I was amazed that they let us pass right by them!

Next, we strolled through downtown en route to the restaurant we had reserved for dinner.

We knew we’d have more time to check out all the shops and galleries, but I couldn’t help but take a closer look at the bas-relief bronze sculpture titled Street Scenes. The 14-ft tall piece reflects the cultural essence of Ashland and its deep connection with theater. The sculpture was cast using real-life local Ashland residents and actors from the Shakespeare festival. It is flanked by donor tiles bearing the names and signatures of community contributors who funded the installation as part of the city’s 1988 Downtown Plan.

Once we got to Cocorico, we found out they couldn’t take us right then but they were able to change our reservation time to an earlier slot. When we came back for dinner, we were plenty hungry! The octopus starter was delicious. I had the pasta while Ash indulged in the mussels. The Biscoff tiramisu was an interesting spin on the traditional dessert and it was also to die for! We were glad we had a 10-minute walk back to our hotel so we can burn at least a few bites of our feast.