John McCaskey has become a central figure in Waipara history and the development of North Canterbury wine. When John travelled to Australia in the early 1960s, he saw the development of vineyards and wines.

Upon returning to Waipara, he decided to take a gamble and planted his first vines in the 1965. Due a freak flood then successive draughts in 1970, 71, 72, the vines died.But never a quitter, John waited until an irrigation scheme, which was approved in 1981, to plant his next vines. In 1986, John and his friends crushed the grapes themselves with their feet. That first harvest produced one bronze for the Waipara Red. John continues to develop new projects such as the House o' Hill Restaurant, to be opened in Summer 2002, a nine-hole golf course and a farm park. Always the consummate dreamer, John has achieved what many called the impossible.