In general, much is known about patterns relating to flood risk reduction, coping, and adaptation in various types of communities; however, knowledge of their drivers—which are critical for building community resilience to natural hazards—is limited. The present study investigates the influencing factors of coping and adaptation measures vis-a-vis flood hazards at the community level and examines their interrelationships. This work employs a “case study” approach and analyzes two towns—St. Adolphe and Ste. Agathe—in the Red River Valley in the province of Manitoba, Canada. Data collection consisted of in-depth interviews with key informants and obtaining oral histories from the locals, along with an examination of secondary official records and documents. The results revealed that the major drivers of local-level coping and adaptation include functioning partnerships among stakeholders, strong institutional structures that facilitate interactive learning, knowledge co-production, resources sharing, communication and information sharing, and infrastructure supports. It was observed that an institutional atmosphere conducive to spontaneous network development yields diverse coping and adaptation strategies. To improve the outcomes of coping and adaptation measures, close collaboration between community-based groups and formal and quasi-formal institutions, and transparency in decision-making processes are vital.