Hello @Wooshness, this is the most common trail in Groot Winterhoek: http://www.cape-hike.co.za/groot-winterhoek/ I havent done it yet.
I believe the paths are signposted and navigation is easy. Just a tip on navigation in Groot Winterhoek - the only good maps available are the 1:50000 topographical maps of SA. The trails are however indicated on this map for the area (3319AA Groot Winterhoek).
I use an app called Avenza Maps, where you can download the 1:50000 topographical maps of SA for free use. It even shows your location on the map itself and can take compass bearings, measure and record routes, etc. (not very accurate but handy nonetheless).
PS, the Groot Winterhoek peak is on my to do list, looks like a real adventure (multi day offtrail self navigated). Its a very prominent peak (2077m), hard to miss once you have spotted it.