Strategies for finding short hiking trails near a driving route in the Pacific North West?

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Google Maps actually can be a good resource for this, though you'll have to do some manual searching. The key is to look for light green spaces in the map view (not the earth view...and this could be a problem if you're colorblind). When you zoom in sufficiently, in most of these the name of that area will appear. You can then click on the name to get more information.

Seminary Hill Natural Area

(I did take a look myself, and there really isn't that much directly next to the route; most places that look like they might be worth stopping at will be at least a few miles out of the way.)

If a name doesn't appear in such an area, it's either private land and not open to the public, a large state or national area of some sort, or Google knows nothing about it for some other reason.

For instance, this route passes through Mt. Hood National Forest, which has its own web site listing hiking trails and providing its own topo maps. From there I can see that you will pass by or near numerous trailheads. I also saw on the website that some trailheads require fees to park your car, so that's something you will want to check in advance.

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