If you want traditional productions with beautiful sets and Equity casts:

Portland Center Stage or Artists Repertory Theatre

If I were going to take a grandparent to see theater in Portland, I’d take them to either Artists Repertory Theatre or Portland Center Stage. Both places put on well-produced plays that make for a nice, if not always artistically challenging, night out. Of these two, Artists Repertory Theatre is my favorite, if for no other reason than they tend to choose riskier material more consistently than PCS. But if you are going to PCS, a pro-tip: The shows in the smaller downstairs theater tend to be more experimental and interesting than the ones in the bigger street-level theater. See you in the basement! Artists Repertory Theatre, 1515 SW Morrison; Portland Center Stage, 128 NW 11th

If stand-up, sketch comedy, or improv is more your speed:

The Siren Theater or Helium Comedy Club

Good news! Portland is home to a strongly established stand-up scene, and a sketch and improv community that’s getting just as big. Get your fill of either with just about anything on offer at Chinatown’s Siren Theater, a performer-owned and operated space that hosts a mix of local performances and out-of-towners. If you just want to see stand-up, Helium Comedy Club is the city’s staple and is heavily considered as our town’s best comedy open mic. The Siren Theater also rents out an attic classroom to Kickstand Comedy Space, where you can see low-key improv jams and local comedians testing out new material on a smaller audience. Siren Theater, 315 NW Davis; Helium Comedy Club, 1510 SE 9th

If you’re ready for things to get weird:

Shaking the Tree and Theatre Vertigo

Ask Portland theater professionals where they see shows in their free time, and chances are good they’ll mention either Shaking the Tree or Theatre Vertigo. I’ll see almost anything they produce, and I can honestly say that I’ve never regretted even the weirdest play I’ve attended at either company. (If you’re wondering: It was Theatre Vertigo’s lengthy murder ballad of a performance, Carnivora.) Theatre Vertigo tends to produce unusual contemporary productions—past topics have included guns in art school, the saddest bachelorette party of life, and love in the information age. If you’re feeling more traditional but still want to see inventive theater, Shaking the Tree is your best bet. Artistic Director Samantha Van Der Merwe’s incredibly immersive productions even make classics from the likes of Henrik Ibsen and Tennessee Williams seem new. Shaking the Tree, 823 SE Grant; Theatre Vertigo, 2110 SE 10th

Seven More Places We Recommend:

Portland Playhouse 602 NE Prescott

Hand2Mouth Theatre 210 SE Madison

Curious Comedy Theater 5225 NE MLK

Profile Theatre 1515 SW Morrison

Third Rail Repertory Theatre 17 SE 8th

Imago Theatre 17 SE 8th

Oregon Children’s Theatre 1939 NE Sandy