Previous field studies monitoring small groups of participants showed that heat stress in the electrical utilities industry may be detrimental to worker health and safety. Our aim in this study was to characterize heat stress and strain in electrical utilities workers across North America. A total of 428 workers in the power generation, transmission, and distribution industry across 16 U.S. states and 3 Canadian Provinces completed a two-part on-line questionnaire anonymously. The first part comprised 13 general questions on the employee’s workplace location, role in the organization, years of experience, general duties, average work shift duration, and other job-related information. It also included two questions on self-reported heat stress. The second part consisted of the “Heat Strain Score Index” (HSSI), a validated questionnaire which evaluates heat stress at the workplace as “safe level” (score ≤13.5: worker experiences no/low heat strain), “caution level” (score 13.6 to 18.0: moderate risk for heat strain), and “danger level” (score >18.0: high risk for heat strain). In addition to the survey, we obtained meteorological data from weather stations in proximity (12.3 ± 12.2 km) to the work locations. Based on the HSSI, 32.9%, 22.3%, and 44.4% of the responders’ workplaces were diagnosed as “safe level,” “caution level,” and “danger level,” respectively. The HSSI varied significantly depending on the occupation from 4.9 ± 3.2 in contact center workforce to 19.1 ± 5.4 in mechanics (p < 0.001), and demonstrated moderate linear relationships with summertime (June, July, August) midday air temperature (r = 0.317, p < 0.001) and outdoor midday Wet-Bulb Globe Temperature (r = 0.322, p < 0.001). The highest HSSI was observed in mechanics, machine operators in line installations, line workers, electricians, and meter-readers. We conclude that electrical utilities workers experience instances of severe environmental heat stress resulting in elevated levels of heat strain, particularly when performing physically demanding tasks (e.g., manually climbing utility poles, installing lines).