Portland has a pretty solid music scene, lots of jazz. Devin Phillips is from New Orleans, killer sax player. Look for him and if he is laying it down, go. BTW, my one son is his bass player.
If there is live music at the 1905 on a Friday night go, plan to stand, seating is limited.pizza slices are excellent, bar is busy, house rocks.
Peruse the Wineries in the Willamette Valley, lots of fun places to do tastings, play bocci and listen to music ( sometimes ) as well.
Great trails on the coast and just about everywhere inland. Both my kids do a ton of hiking out there.
There are many cool neighborhoods to check out where the Main Street is restaurants, bars, music shops, other shops, etc. etc.
Go to Proud Mary’s for breakfast, sit at the counter.
If you can get a seat at a communal table at Han Oak grab it.
Screen Door, another killer spot for Brunch. My sous chef son digs Nomad.
One of my favorites is Laurelhurst Market. Stand outside on the patio, have a glass of Pinot Noir before being seated. Great place.
If you like books, Go to Powell’s downtown, a full city block of happiness. Very cool to experience.