Another ride you could keep in mind is
Ride the Rim. Usually in September, half of Crater Lake is closed to traffic and for bikes.
There is the
American Lung Association Reach the Beach ride. It used start in several places including Monroe, Oregon. But they've changed to only start in the Portland area, heading to Lincoln City.
Do you run? Perhaps the
Hood to Coast relay There is also the
Portland Marathon
Keep your eyes peeled for
Pedalpalooza, a whole month of bicycle activities in the summer.
Check out TravelOregon. There are several
"Scenic Bikeways". I've been up and down the Willamette Valley Scenic Bikeway several times.
https://traveloregon.com/things-to-d...ion/bicycling/
HWY 242 (McKenzie Pass) is very beautiful. It is closed now, but they allow cyclists to hop the gate and ride up the hill with cars. I don't remember when it is opened to cars, but it would be a good ride for late May or early June.
HWY 101, Oregon Coast is also popular, but expect a narrow road with lots of traffic.