I did a solo bushwhack to Middle Osceola (4200-ft) and West Osceola (4114-ft; White Mountains, NH) in August 2005. I left the Mt. Osceola Trail at the west end of the last switchback; then followed the ridge to the two summits. It took 2 1/2 hours over to West Osceola and back, wandering on and off herd paths through open woods and nasty thick stuff.
Since it was nearby, I went over to Mt. Osceola for its fine view, where I found a mom-and-son hiker pair there ahead of me.
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NH Mountain Hiking