Macclesfield was settled in 1840 and began producing wine in 1844, when the first exports of fortified ports were shipped to the Court of Queen Victoria. Macclesfield claims history as one of the earliest wine areas in Australia and now produces world renowned cool climate reds, primarily Cabernet Sauvignon and Shiraz, as well as dry, delicate Riesling and Viognier.

Sir Samuel Davenport surveyed the property around 1840 as a part of the area's subdivision. Davenport planted the first vineyard of the district in 1842 and opened a very English style pub -The Three Brothers Arms, in 1844. The Hotel still exists today. By 1904 the approximate 500 acres of planted vines had largely been taken out and replaced with dairy herds and orchards. It was not until 1996 that replanting began when it was recognised how unique the soil structure and microclimate of Macclesfield were.

Bendbrook Vineyard was planted in 1997. The name Bendbrook comes from the significant bend in the Angas River that runs through the middle of the property, separating the Cabernet Sauvignon vines from the Shiraz.

This has at times made life very interesting when the river floods, as it does every 4-5 years (2004 flood, third picture below). Historically known Bendbrook's homestead was originally the Postmasters residence, which has been recently restored in classic early Australian farmhouse style. Now residence to the Struik family, it is also known as Bendbrook Wines' Cellar Door (by appointment only).