Jan van Riebeek named this pass Clooff Pas when he passed through in 1657. He thought the kloof would be difficult to fortify against the Hottentots because of its width.
Constantia Nek was the connecting link between Hout Bay and the settlement. A rudimentary road was fashioned and when it was discovered that there was a better source of timber than the Kirstenbosch area, viz that of the "Hout Bay Valley", van der Stel ordered that the road be widened and improved in 1679.
By 1787 the road reached as far as Kronendal farm but further than that the road was broken up with deep excavations as part of the French defensive lines against British attack.The road was dug up and an earthen fort was erected, the remains of which can still be seen not far from Constantia Nek Restaurant.
The fort was named the Conway Redoubt, after Colonel Thomas Conway, an Irishman who commanded the Pondicherry Regiment at the Cape. Here the French troops waited for the attack that never came. A signaling station was also set up at Constantia Nek to give warning of ships entering Hout Bay. The peak behind the Constantia Nek Restaurant now called Vlakkenberg, was originally called Vlagenberg (Flag Mountain).
Development of the road was low on the priority list and although some alterations were made through the years, the most notcieable being in 1804, the traffic had increased sufficiently that in 1933 the road was extended to the Hout Bay Hotel.
The modern road is a winding single lane, which leads through the burgeoning suburb of Hout Bay and onto Chapman's Peak. It forms part of the "All Round the Cape Peninsula Road", which incorporates amongst others Chapman's Peak and Victoria Drive.