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i dont know portland at all, so i cant really give you any advice on trails.
what i did notice is that you're doing this hike alone??
i wouldnt recommend that you hike alone. EVER. always take someone with you no matter how small the hike is. If you're adamant about going alone, make sure you let someone know exactly what trail you're doing and that you have safety gear with you in case you get lost.
I have a few friends that got lost on a mountain here not so long ago. after a hard days trek, and provisions and clothing only for a day trek they were exposed to the harsh realities the night brings. it wasnt a pleasant experience from what i hear. so if you dont have safety gear ( ie. as a minimum that would include compass, maps, possibly a flair, satellite phone or phone reception, a full battery and a car charger to charge every day and food for 2 days & 2 nights including the provision that you sleep overnight) then i wouldnt recommend you go alone. always err on the side of caution.
sorry for the thread jack, but it needed to be said i think.
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