Freezing rain is an especially hazardous winter weather phenomenon that remains particularly challenging to forecast. Here, we identify the salient thermodynamic characteristics distinguishing long-duration (six or more hours) freezing rain events from short-duration (2–4 h) events in three regions of the United States and Canada from 1979 to 2016. In the northeastern United States and southeastern Canada, strong surface cold-air advection is not common during freezing rain events. Colder onset temperatures at the surface and in the near-surface cold layer support longer-duration events there, allowing heating mechanisms (e.g., the release of latent heat of fusion when rain freezes at the surface) to act for longer periods before the surface reaches 0°C and precipitation transitions to rain. In the south-central United States, cold air at the surface is replenished via continuous cold-air advection, reducing the necessity of cold onset surface temperatures for event persistence. Instead, longer-duration events are associated with warmer and deeper >0°C warm layers aloft and stronger advection of warm and moist air into this layer, delaying its erosion via cooling mechanisms such as melting. Finally, in the southeastern United States, colder and especially drier onset conditions in the cold layer are associated with longer-duration events, with evaporative cooling crucial to maintaining the subfreezing surface temperatures necessary for freezing rain. Through an improved understanding of the regional conditions supporting freezing rain event persistence, we hope to provide useful information to forecasters in their attempt to predict these potentially damaging events.