is it possible to ride from winter hill?

I know there’s a path but is it ridable?

Yes, the path from Horden Stoops over Redmond Edge is perfectly ridable but gets a bit damp on the initial section. Later, towards Great Hill, its flagged.
HTH

I only ever take that route when its either frozen solid or bone-dry.
Great Hill ain’t all that great to be honest. There are better options to either side IMHO.
Personally,I’d take the Belmont Descent then WWW towards Roddlesworth in preference… or Ice Cream Run and cheeky lakeside path towards White Coppice if you want/need to be on the other side of the Hill.

which belmont descent? the one that spits you at at san mario’s?

Yep, from San Marino you can soon pick up Witton Weavers’ back to Roddlesworth or take in Darwen Tower too if you want more.
Either option would probably be a better bet than fighting through the boggy bits above Horden Stoops at the moment (save that for summer instead).