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 μg/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 µm) phase. The highest fenarimol concentration (~10 μg/L) was detected in the first main runoff event in April 2007 and the average concentration for the duration that it was detected during April to early June 2007 was 4.3 μg/L, which are 10 and 4.3 times, respectively, the Australian drinking water guideline (DWG) (1 μg/L). Fenarimol was detected in 19 water samples collected from early April to early June 2007 and in 95% of these cases the total concentration exceeded the DWG. In all seasons monitored fenarimol moved predominantly in a soluble (<1.2 µm) phase. The results from this study indicate that pesticides are of concern in this catchment and strategies for minimising off-site transport need to be developed and evaluated. Data about the mode of transport will have implications for the choice and efficacy of mitigation strategies.