I drove through a lot of Oregon the end of July. You probably aren't going to be put in Mt Hood, because its wet. However, that place is beautiful.
If you have anytime off, maybe you could go ride some mootin bikes at the ski resorts. It isn't that far from Portland. The coast is sweet, maybe go to Astoria (again not that far from Portland) and reenact your favorite lines from the Goonies. "These are my dreams, my wishes and I'm taking them back. I'm taking them all back."
Highway 97 is wonderous, its like that Red Dead Redemption. Canyons, desert, rivers, high elevation pine forests, volcanic legacies.
The 5 isn't anything special. Highway 128 is fucking sweet! The North Umpqua river winds through a canyon. If you're that far south, Crater Lake is a must.
The coast is really special. You're probably not going to find a beach were people are pretending its San Diego but worth checking if you love the sea. I love the sea.
Now for family vacation photos of Oregon from the other week.
Upstream from Toketee falls. I really wanted to swim here.
Toketee Falls
Crater Lake with Dorothy Helen
Somewhere on Highway 97