I looked at his trip map and had the question of what town in central Kentucky is he visiting and why?
Bardstown. Bourbon Trail.
Could be Bowling Green for the Corvette museum.
We are following the route just to get a rough order of states. Then when we get to each state we make a list of where we want to go and plan a route.
Here is our Oregon route.
Lava Beds National Monument
Crater Lake National Park
Oregon Caves
Boardman State Scenic Corridor
Oregon Coast Trail
Portland
Columbia Ri ER Gorge
Mt Hood
See if you can get into Silver Falls State Park (about 1.5 hours south of Portland). Great waterfall hikes. Swing by McMinnville to see the “Spruce Goose” (also an indoor waterpark, btw). Mt Hood is a mountain, special to Portlander’s but otherwise nothing remarkable about it. But not far away is Mount Saint Helens, which I find more interesting. Mount Rainier is also better to visit than Mount Hood. I’d avoid the whole area in the late summer wildfire season as road closures become unpredictable and views at e.g. Crater Lake are likely to be smoked out.