I’m not sure how far into Oregon you were planning on driving, but if you’re looking for atmosphere in the southern part of the state, Ashland is the town for you. Surrounded by mountains (Cascades and Siskiyous), its vibe is about as European as you’ll find almost anywhere in Oregon.
Just off Interstate 5 and just north of the California border, Ashland arguably is the region’s main tourist destination. The small, walkable downtown area is full of historical buildings, along with the Railroad District, which is an easy walk of several blocks. Lithia Park is one of locals’
favorite spots for easy, picturesque hiking. Ashland has a wide variety of restaurants and accommodations from bed-and-breakfasts to high-end hotels, plus the Oregon Shakespeare Festival, Cabaret Theater and a vibrant arts scene.
Ashland makes a good home base for exploring the region’s other attractions. I couldn’t agree more that Crater Lake is a must. The drive from Ashland to the national park takes about two hours.