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This is an odd sort of question because whatever is your least favorite trail, why would you ski it more than once? Most of the nominations will probably be trails you have to ski to get to or get back from your favorite trails. One I've heard people complain about but I don't actually mind is the runout from the Kidderbrook trail at Stratton. It has enough pitch to be an easy coast, just one narrow place I'd rather not squeeze through with other skiers. I'll nominate Roaring Brook at Belleayre, an underachiever. It's good as an easy way down, but because of its man-made cut-and-fill unnatural terrain I find it very boring.
Lower Trigger at Gunstock. Gunstock has some awful run outs and this one becomes the worst, but doesn't have to be. They rope off access to Smith where you could continue down relatively painlessly to the High Speed Quad and instead force you over to Lower Recoil then Musket to get back to the lift. Sooooo annoying.