Extreme precipitation events in recent years in the Northeastern U.S. have resulted in catastrophic flooding and damages to personal property, commerce, public infrastructure and communities. In the northern Appalachian mountains of this region, flood damage vulnerability is exacerbated by steep terrain, narrow river valleys through which flood waters flow, and historic human settlement patterns. Here, we present preliminary analysis of compound and cascading flood damages resulting from flood events in 2023 and 2024 impacting the region, including damages from floodwater inundation and fluvial erosion. We evaluate key drivers of damages, including landscape setting, antecedent and storm conditions, and the presence or absence of intact natural infrastructure (forests, wetlands, floodplains) thought to mitigate flood damages. Damages in steep headwater settings, particularly along rural road networks, was associated with cascading down-network flood damages across the watersheds experiencing extreme precipitation. The presence of hydraulicly connected floodplains and compliance with newly-mandated stormwater management practices on rural roads were associated with reduced damage impacts compared to settings without these natural and managed interventions. Our results are relevant to planning, regulation and conservation efforts to build flood resiliency in mountain settings.