That's probably one of the three worst I've dealt with. The trail mostly goes over solid rock so there's no easy treadway to follow
But that Hang Glider area, besides having the solid rock treadway which isn't easy to follow and twisting around a lot, had very old and faded blazes. Sometimes it gets where you're confusing the blazes with lighter-colored lichen that happens to be growing in a more or less rectangular shape.
Probably the next most difficult blaze hunt was around the top of Schagitcoke Mtn. south of Kent, CT. The last blaze is just before the trail comes in from the west and descends down into a mostly solid-rock gully. There's something that looks a lot like a treadway (especially since a large log lying across it has the center chainsawed out) that heads straight north out of the gully. But this isn't the treadway. The actual treadway follows around first SE, then making a sharp left and heading North, then heading NE and crossing over a brook. I actually found the trail by following the flase treadway to a brook, looking on my GPS to see it was saying the trail was somewhere to the east, then following eastward along the brook until there was a brookside tree with a white blaze. Visibility also made this whole search tough. It was late on an overcast day, late in October.
The top award goes to an area about a mile or so north of the US7 road crossing near Great Barrington, MA. This is an area where, even though it's not solid rock, the ground is kind of hardish and there's no easy to see treadway. There were actually two or three spots before the really tough one where it was necessary to back up to the last-seen blaze in order to regain the trail.
But the last blaze before the really tough area was on an odd tree, a tree that grew about five feet out of the ground, then grew parallel to the ground, then grew straight up toward the sun again in a conventional fashion. This was on a nice, bright, sunny April day (temp in the 70's). One of the first in that long string of clear, warm days we had throughout the Spring, Summer and Fall of 2010. Anyway, I kept looping back to this odd tree and then trying to go forward again, carefully trying to suss out what could be the treadway. For a long time, it did me no good. The next blaze was just not to be found. I knew that, in general, as shown on my map (I wised up and went with maps instead of the GPS) it was in an NE direction. But this general knowledge wasn't helping. I finally had to apply an improvised grid-search and about 20 minutes later I stumbled upon the next blaze. The Berkshire AMC did get an e-mail on that one.
Thanks Laurie. It happens that I was recently reading the Sixteenth Edition of the Appalachian Trail Guide to NY-NJ. The Questions and Answers section in the back of the book had very interesting reading on trail design. Apparently the AT was neither designed to torture nor to delight hikers. In fact, the enjoyment, or lack thereof, is secondary to factors like minimizing impact on the terrain (in current design that is). This may explain why Mt. Everett in southern MA uses the draw-a-straight-line-from-the-bottom-to-the-top design rather than the zig-zags often used for ascending trail sections in more recent layouts. Then again, that Everett ascent from the south is pretty much solid rock so the impact-minimizing zig-zag style course would not have really been needed so much here.
Ah, there's a madness to their method. The problem is that the treadway isn't always obvious, especially to people who don't know the trail by heart (it's likely that many of the local club maintenance crew people already know the trail well enough to not need blazes anyway).