Automated radio telemetry systems have become a popular and invaluable tool in tracking the activity and movement of wild animals. However, many environmental conditions can hinder accuracy when tracking with this technology. For instance, study sites may contain multiple habitat types, each habitat uniquely affecting the signal strength received from tagged species. To investigate the influence of a structurally diverse study site on an automated radio telemetry system, we conducted this project at a restored and managed pine barren habitat that consisted of a mix of mature pitch pine, treated pitch pine, scrub oak, and hardwood forests. This site, Montague Plains Wildlife Management Area, Montague, Massachusetts, is also a known breeding ground for Eastern whip-poor-will (Antrostomus vociferus). To measure the relationship of radio signal strength with distance across each habitat, we used radio telemetry equipment manufactured by Cellular Tracking Technologies. We produced negative exponential decay functions measuring radio signal strength over distance and tested for differences among habitat types on radio signal strength (RSS). We found that decay function parameters significantly differed by habitat type, prompting us to investigate if accounting for these differences improved location estimate accuracy. To test this, we estimated known locations using trilateration methods with and without habitat calibration. Comparing these tests indicates that habitat-specific adjustments significantly improved location accuracy. Lastly, we visualized estimated RSS-based locations of 1 week of whip-poor-will data and compared them to GPS data generated from the same individual. Previous studies have accounted for types of environmental interference (like elevation) in the field but have avoided incorporating habitat-specific factors by working with node networks covering a relatively small area, but in this study, we examined the potential to scale up for larger areas and in more complex habitats.