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Local runoff from the catchments in the Mount Lofty Ranges watershed provides a major source (up to 60%) of drinking water for the city of Adelaide, South Australia, Australia. In this study two major land uses (apples and cherries) in the Mount Lofty Ranges were monitored for off-site transport of pesticides over approximately 30 months. The pathways of off-site transport (soluble or colloidal) of pesticides were also monitored. There were several pesticides detected in surface drainage water from the apples site but two pesticides (chlorpyrifos and fenarimol) were of particular concern. The average chlorpyrifos concentrations were 0.12 and 0.15 g/L in 2007 and 2009, respectively, which are more than ten times the Australian environmental guideline value, suggesting potential deleterious effects on aquatic organisms downstream of the apple site. The form in which chlorpyrifos was transported off-site varied throughout the season but over time a greater proportion moved in the soluble (<1.2 m) phase.