If you really want to make sure you end up by yourself in the Wallowas, you can start on the South side of the range near Halfway, OR. The one caveat to coming this way is that you need to make up your mind and commit early – before you even start driving because the entry points are very far from each other, driving-wise. Joseph and Halfway are only about 30 miles apart across the mountains, but it is either a 2.5-hour, 70-mile drive over forest roads, or 3 hour, 160-mile drive via highways! There are fewer trails to access in the South region, but the views are still incredible, and it is easy to find alpine lakes and vibes. One destination is Crater Lake (not that Crater Lake). This is about a 14-mile round-trip hike from the East Eagle Trailhead with about 3500 feet of elevation gain.
Again, for the peakbagger, this section also contains a county high point – Red Mountain. Climbing the actual summit is actually just a slog up from Crater Lake up a loose talus slope and should not be taken lightly. It will add about another 3 miles round-trip and another 1800 feet of elevation gain to get to the summit, but it is a very slow and challenging 1800 feet. Another starting option is from Summit Point Trailhead. This will cut off some elevation gains, but getting to the trailhead is a little trickier, and the trail itself is a bit more technical.
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