It contains dozens of climbing routes up limestone, ranging from short problems to 350ft+ multi-pitch climbs. The climbing areas are Woodcroft quarry, Fly Wall, Go Wall, South Bay, Far South Bay, North Wall, and far North Wall.
Woodcroft quarry is behind fly wall and is the most recently developed area, routes are still being added (2007/2008). The majority of the routes in the quarry are bolt protected sport routes of varying degrees of quality.
Fly Wall is a multi pitch cliff. It is relatively steep, containing 2 routes at HS grade, approximately 5 at VS and the rest are HVS - E5. The easier routes tend to suffer from polish.
GO (= Great Overhanging) Wall is the largest cliff at wintours and contains 4 and 5 pitch extremes. The routes here are multi pitch 'trouser fillers' all of which are technical and steep. Many break through the massive overhangs near the top of the wall. The routes are in the range E2 - E6.
The southern bays contain a number of easier and very good multipitch routes in the grade range of Mod - E2.
The north wall consists again of rather steep multi pitch routes. Although there are 2 HS routes, and a number of very good VS routes
The far end of north wall is again very steep with stepped overhangs. The rock is also very compact, not lending itself to traditional protection. There is a lot of fixed gear here.
Wintour's Leap is named after Royalist Sir John Wintour who, hotly pursued on his horse by Parliamentary forces, survived a legendary leap off the cliff and, landing safely in the Wye below, swam to his safety in the nearby Chepstow Castle.