A brilliant trail when deep frozen and/or under hard-packed snow when it has echoes of the arctic about it. Properly atmospheric in the same conditions at night. If you’re doing it as part of a bigger loop via the Roych or Jacob’s for example, you can avoid riding on the Woodhead or – heading uphill – the super-rutted Snow Road, by cutting over to the Trans Pennine Trail near the Flouch, following it to Dunford Bridge then heading left up the road to pick up the Longdendale Trail where it hits the Woodhead.
As far as Cut Gate in the wet goes, it’s not much fun for most people and nasty in strong winds. It’s one of those trails that’s blindingly good when it’s bone dry and/or frozen solid, but a special sort of ‘fun’ otherwise. Personally I’d wait for it to freeze, but ymmv etc.
Oh, and the Jacob’s / Roych loop is – as people keep posting – a good all-weather bet, though eventually it’ll become the only route people ever ride round here and degenerate into a 16km rut… 😉