Located just a few miles north of the California border, the former mill town of Ashland is a cultural gem, famous for its quaint downtown and months-long Oregon Shakespeare Festival.
Standing out from the more agricultural cities of the region with its unhurried, artistic, hippie-friendly vibe, Ashland compels you to slow down and meet its pace, surrounded by farmlands and forests. There’s a proud sense of style in every block here—48 of the town’s buildings are on the National Register of Historic Places. Ashland’s famous Shakespeare festival celebrates the Bard, sure, but salutes other playwrights as well, and crescendos in the summer. A highly walkable downtown is full of restaurants boasting the area’s best dining.
Here in the Siskiyou Mountains, hills are low and rounded, covered with trees. Although Ashland is on the west side of the Cascades, it’s not as rainy as most of Oregon’s western side; the climate is a bit drier and a little sunnier, like a mix of the state’s two sides. The Rogue and Klamath Rivers slice through the region, with Ashland up a low valley on one of the former’s tributaries, offering recreational opportunities for white-water rafting.
Just a short drive away, the wild side of Oregon is on display at stunning Crater Lake National Park. A brilliant blue and formed by a volcanic eruption, Crater Lake is the deepest in the country and the state’s only national park. The pace may be languid in southern Oregon, but there’s much to discover.
If you’re visiting during Ashland’s famous Shakespeare festival, which runs most of the year (Feb.-Oct.), book tickets to plays you might want to see in advance and build your time here around performances. For shows in the height of summer, book tickets in early spring; outside this high season, you can typically book tickets a few weeks in advance. The town itself can be seen in a day, but stay overnight if attending a night show.
A white-water rafting trip or an excursion to Crater Lake National Park deserves at least an entire day each—don’t try to mix them in with a Shakespeare day. Once off the interstate, travel can be slow on the small rural roads, so you’ll want to build in plenty of time to get into the wilderness and then back out. In summer at Crater Lake, visitors can explore plentiful hiking options, drive the entire circumference of the lake via the Rim Drive, and take boat tours. In winter, there’s snowshoeing and a meal at Crater Lake Lodge to fill the time.