During the 1930's land in the Hangklip area between the Palmiet River and the Rooiels River was acquired by three business partners, Harold Porter, Arthur Youldon and Jack Clarence. They called it the Hangklip Beach Estates and divided the area into three townships, namely Betty's Bay, Pringle Bay and Rooiels and sold off plots to interested parties. Until the Second World War, when the coastal road from Gordon's Bay (named Clarence Drive after Jack Clarence) was built to service the radar stations at Stony Point and at Hangklip, this area had been accessed via Sir Lowry's Pass and Kleinmond with a pontoon crossing the Palmiet River.
While the spectacular Clarence drive was cut out of the cliff face to connect the many little hamlets that lie along this part of the coast, a jail was necessary to house the prisoners doing the hard work. At this time, the original structures of what is now Glen Craig was built by the prisoners in the form of a rectangle, with a 'parade ground' in the middle for their exercise.
The story goes around that Glen Craig also housed Italian Prisoners of war. There is reference to this fact in the now out of print "Fynbos Coast" written by Peter Slingsby There are lively rumours of the doings of previous inhabitants when it was a jail, and two sentry boxes stand testament on the NW side and SE sides of the property.
Since it is over 60 years old, Glen Craig has been declared a heritage site. The property looks down the hill towards the sea and the quaint village of Pringle Bay with its unspoilt natural beauty and peaceful pace. Over the years the village of Pringle Bay has attracted many resident talented artists, musicians and academics with their varied skills. "Arende", the TV show, was filmed on this property.