Spotted wing drosophila, Drosophila suzukii (Matsumura) (Diptera: Drosophilidae), was monitored from 2010 to 2014 in 314–828 sites located in interior fruit-growing regions of OR and WA, United States, and BC, Canada, using traps baited with apple cider vinegar or sugar-water-yeast. Seasonal population dynamics and sex ratios were summarized for berry, cherry, stone fruit, grape, non-crop host plants, non-host sites, and for conventional IPM, certified organic, backyard, and feral sites, by region and year. Overwintering was detected in all regions and years, despite winter temperatures below -17°C. A spatial analysis was conducted using a Geographic Information System (GIS), daily weather data, geomorphometric measures of terrain, distance to water, and other variables, at each site. Overwintering success at a site, measured as Julian week of first capture of D. suzukii, was significantly related (R² = 0.49) in cherry habitats to year, agronomic treatment, and number of winter days with temperatures >-5°C. In berry, cherry, stone fruit and grape habitats, 2011–2014, it was significantly related (R² = 0.42) to year, agronomic treatment, the logarithm of peak population of D. suzukii in the prior autumn, latitude, elevation, and topographic wetness index. The results show that D. suzukii has adapted to exploit a succession of irrigated crops and feral habitats in mixed landscapes of a semi-arid region with cold winters and hot dry summers, and are shaping strategies for pest management and for biological control.