The Cascade Festival of Music is coming up at the end of this month, from August 26th through September 2nd. The concerts each day take place in Drake Park, and tickets range in price from $15 to $38. (Although you could just hang out around the park and listen to music for free… not unlike floating the river during concerts at the Les Schwab Amphitheater.)
And lest you think the Festival is all about classical music, not so! In fact, one of the concerts is "A Tribute to Ray Charles" featuring a "who’s who of Oregon blues and jazz musicians." This would be the concert I’d attend.
And on Tuesday the 29th, there are even some free children’s events during the day, including an "instrument petting zoo," a concert, and Ben & Jerry’s ice cream.