This is one of my favorite Portland festivals, and not just because of the strolling accordionists. I recommend arriving early to secure a table in the beer and wine garden at the top of the bowl on the SE side of the square. You’ll have an excellent view of the stage in the middle of the square. Wine is available by the bottle or the glass; and you’ll find the Festa Italiana drink prices to be more reasonable than at most festivals. Beer is available too.
Italian and Italian-ish restaurants (including Piazza Italia, Bastas Trattoria, La Bottega, a Cena, Mita’s Italian Ice, and Gelato Maestro) from all over set up shop in the square for the festival, offering gelato, pizza, etc.
The entertainment line up is impressive. Musicians from all over regale the crowds with everything from opera to Sinatra, and plenty of accordion. In addition to the music enjoy the grape stomp competition, cooking and pizza tossing demonstrations, marionette shows, and folk dancers. Check out the whole event calendar here.
Admission is free. Hours are noon until 11pm Thursday and Friday, and 11am until 11pm on Saturday.