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I am planning a 50 mile hike for our Portland area Boy Scout troop this summer (week long). Our initial plans are for either the Mt. Hood loop, or something along the Coast Range. First time for many of these boys, trying to give them a good experience, find something with lakes to swim and fish, but not too difficult. Ideas? thanks!
I'm assuming you are planning on staying within a reasonable distance to portland. If not, I would suggest the Wallowa's. In my opinion it's as amazing as it gets. The timberline trail is a good choice. I believe it is around 40-45 miles. I did it in two days two summers ago. I wish I had taken at least 4 to see some of the stuff I had to blaze pass. There are no lakes on the trail, but a couple side trips could take you to burnt and cast lake. There might be others within a close distance of the trail. Considering the snow this season, steam crossings could be difficult if not dangerous until later in the season. Goat rocks might be a good option as well. I think you could make a loop trip on some trails up there.
Mt. Hood Loop would be a good starter (check the trail conditions, I've heard it was pretty bad last year). You'll have a hard time finding a trail of that length in the Coast Range unfortunately. Other options include: Mt. Jefferson Wilderness - start at santiam pass and hike the Pacific Crest Trail north until reaching Olallie Lake. This is one of the best sections of PCT in Oregon. Lots of lakes in the Jefferson Wilderness, you can rework the trip to hit additional lakes. Three Sisters Loop - Hike PCT, circle around to the east side of the peaks, past Green Lakes. I think it's 50 or 60 miles, but would be an amazing trip.