It's a day trip from Portland, but it's impossible not to mention Oregon Shakespeare Festival (OSF) when talking about the arts in Oregon. Presenting a multitude of diverse works by Shakespeare and others, this is the most famous theater festival in Oregon. It takes place in the quaint town of Ashland which is worth a visit even if you aren't in town for OSF.
Head down I5 to Ashland - it's a 4.5-5 hour drive, so plan to stay a while and see a few shows!
15 S Pioneer St, Ashland, OR 97520, United States