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In the 1950’s and 1960’s the town had a flourishing farming Community, which was severely compromised when the main road between Johannesburg and Durban was upgraded and a bypass was built around Greylingstad - causing small businesses in town to lose a lot of customers.

Greylingstad does, however have a rich history: During the Boer War the Scottish Rifles built a number of small forts overlooking the town and the farms beyond the hills. The Scottish Rifles laid out the initials "SR" on the hill overlooking the town, and it was always clearly visible from the main street of Greylingstad. If you climb the steep kopjie you will enter a unique portal into the past - the ruins of a British Army fortified campsite that was built and occupied between July 1900 and June 1902. The fortifications, gun pits, tent lines, stables and even the parade ground are in pristine condition - only the tents, equipment and soldiers are missing.