Josh made Calera's first wine in 1975, 1000 cases of zinfandel, produced from purchased grapes. During his first two years as a winemaker, he made the Calera wines in a rented space in a larger nearby winery.

In 1977 Josh purchased property on which to build the winery. He chose a 100 acre site on Cienega Road halfway between the vineyard and the town of Hollister. Located 1000 feet lower in elevation than the vineyard, this property was blessed with the all-important attributes of a paved road, and both telephone and electrical service (services which to this day are unavailable on Mt. Harlan).

On the Cienega Road property. a multi-level rock crushing facility had been built into the steep hillside in the 1950s. The facility was abandoned before it was ever used for crushing rock, but 20 years later the walls and terraces, with some substantial seismic retro-fitting, (the San Andreas fault lies just 100 yards away) became the heart of Calera's gravity-flow winery. The multi-layered hillside construction has allowed for the gentlest possible handling of the Calera wines. Wines move through the winemaking process by the mere force of gravity, rather than by the use of pumps.

After decades of improvements and construction today the winery boasts barrel cellars built into the hillside, additional warehouse space, an underground wine library, offices and a laboratory (a major improvement over the previous 50' office trailer), a top-of-the-line German grape press, and most recently, a new Italian bottling line.