The Greater Simonsberg sub-route gets its name from the mountain of the same name, in turn named after the 17th century founder of Stellenbosch, Simon van der Stel. The area lies to the north-east of the town, and incorporates the Jonkershoek Valley to the R44 towards Paarl. It is bordered in the west by the Plankenburg River, one of the many watercourses that suppy the surrounding vineyards and orchards.
Greater Simonsberg is among the most mountainous sub-routes of the Stellenbosch Winelands. It enjoys abundant natural wilderness, protected by the Greater Simonsberg Conservancy and the conservancy in the Banghoek River Valley. Klapmuts Hill is also regarded as a critical biodiversity and ecological support area. Recognising the importance of these reserves to agriculture, all the local wineries have introduced active conservation programmes.
Wineries in the Greater Simonsberg sub-route include: