Perfluoroalkyl and polyfluoroalkyl substances (PFAS) are a group of notoriously persistent and water-soluble chemical compounds that can be found worldwide. Most PFAS are highly toxic and can bioaccumulate via food chains. PFAS enter the environment through point and non-point sources. Point sources include manufacturing plants and areas with regular use of aqueous fire fighting foams (AFFF), such as airports, military bases, and fire halls. Non-point sources involve water runoffs from agriculture, industry, or wastewater treatment plants (WWTPs), as well as atmospheric deposition. Firefighting wastewater in effluent from WWTPs is considered one of the main sources of PFAS in the environment. The pervasive presence of PFAS in aquatic environments poses a substantial concern for military installations across Canada. This research focuses on identifying the pathways that PFAS follow as a result of military activities, and how they can impact drinking water sources. Related sampling methodologies are investigated to optimize PFAS monitoring; seasonal training schedules and patterns of dominant PFAS types (short chain or long chain) are also part of this study. A mixed-method research methodology is employed for this purpose, with integration of quantitative and qualitative data. Quantitative data have been collected during environmental monitoring programs, while qualitative data are used to interpret measurable parameters. The overall expected outcome is to inform PFAS management and associated monitoring practices, with a view to optimizing the protection of drinking water sources from these “forever chemicals.” The recommendations from this investigation could be extrapolated to support the military as well as manufacturing sectors and municipal facilities requiring PFAS contamination management.