Current climatic projections show clearly that increasingly more extreme weather events are to be expected in the future. Historic buildings are considered to be the most vulnerable to this adverse climatic impact, via moisture induced deterioration and resulting strength decay in their construction materials. Therefore, the identification of these climatic effects is important to be able to develop suitable tools to mitigate them, both for individual buildings and on a regional scale. This paper presents the analysis of a comprehensive environmental monitoring of two historic buildings in Tewkesbury, Gloucestershire, UK, to provide thorough insight on their performances under environmental loading on a comparative basis. Firstly, the effect of wind-driven rain (WDR) and flooding is assessed by correlation with relative humidity (RH) measurements. The WDR measurements are then compared against values calculated using well established semi-empirical models and reasons behind the limited correlation are discussed. The dynamic hygrothermal response of two different historic fabrics is studied in greater detail by monitoring in-wall temperature and RH. The conclusions drawn from the analysis of the monitoring outputs are then further elaborated on by using hygrothermal characterization obtained by dynamic vapour sorption (DVS) testing of material samples extracted from the fabric of these buildings. The study concludes that the current environmental conditions pose a threat on the building envelopes unless routine maintenance is provided, and that monitoring methodology devised is clearly successful in quantifying the exposure of the two historic buildings to environmental conditions, onsetting deterioration phenomena in the envelop materials.