Historical extreme events such as floods and droughts can be documented in a variety of ways. These include meteorological observations and social reports, with narrative descriptions of extreme events and accompanying impacts. Here we look at how both these means of recording events can complement or contradict each other, in a quest to examine extreme events from quantitative observations and disruptive events from a descriptive viewpoint. The NORTHERN (Nineteenth-century Overseas Records Transcribed for Historical Environmental Reconstruction of the North) database contains over 1.8 million observations from 45 stations and 15 categories of weather observation type. Included in these are both numerical observations of precipitation events, including amounts, timing, and duration of events. Floods are the weather event most often described in newspapers and are occasionally captured in these precipitation fields. Flooding is often the outcome of complex seasons-long interactions between groundwater recharge, spring thawing of the ground, and snowmelt. Drought and the often-corresponding wildfires are similarly of great concern in many parts of Canada and tend to be recorded more in descriptive fields such as weather remarks and casual phenomena. By comparing the numerical and descriptive sources in the past and present, we can gain a better understanding of the nature of these events and the impacts, vulnerabilities and resiliencies to these events.