Win Hill is commonly ascended from Yorkshire Bridge or Hope. The ascent from Yorkshire Bridge is a steep climb of in by Parkin Clough, first through woods then over the moor to the top. Routes from Hope are gentler, either via Twitchill Farm or the villages of Aston and Thornhill. Depending on direction of travel, Win Hill is either the first or last hill on the Derwent Watershed and Edale Horseshoe challenge walks.