I'm not a local so can't speak to what may be going on when you visit, but I love visiting Portland! I have a good friend who lives there, so have been out there 3 or 4 times, and had a great time with each visit - including my most recent trip a month ago which was for me to run my first marathon!
A few suggestions for destinations - Multinomah Falls, or some of the local parks are lovely to hike around. The coastline is really beautiful and not a far drive, if you want to spend a day or two there. Powell's bookstore is a great place to hang out and look for something interesting to read. The "Pearl" district has lots of good restaurants.
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