The invasive Halyomorpha halys invades crop fields from various bordering habitats, and its feeding on crops has caused significant economic losses. Thus, H. halys is considered a perimeter-driven threat, and research on alternative management tactics against it has focused on intervention at crop edges. Woodlands adjacent to crop fields contain many hosts of H. halys and are therefore considered “riskiest” in terms of pest pressure and crop injury. However, tree fruit orchards in the Mid-Atlantic, USA, are often bordered on one or more sides by woodlands and other habitats, including other tree fruit blocks, and field crops. Monitoring H. halys using pheromone traps has most often focused on the crop–woodland interface, but the relative effects of woodlands and other habitats bordering orchards on pest pressure and crop injury have not been examined. A two-year study comparing seasonal captures of H. halys and fruit injury among different habitats bordering commercial apple and peach orchards in the Mid-Atlantic revealed that while woodland borders often posed the greatest risk, other border habitats also contributed significantly to captures and injury in numerous instances. The relevance of these findings to refining and optimizing perimeter-based monitoring and management approaches for H. halys is discussed.