This article contributes to the literature on population aging and community development by exploring whether decision‐makers at local levels of governance in Canada subscribe to an age‐friendly or apocalyptic demography view of their older populations. Drawing on a qualitative analysis of six medium‐sized cities in Ontario, we capture the views of local leaders in different economic, demographic, and geographical contexts to understand the challenges, implications, and opportunities for community development as their populations age. We chose to capture the regional differences that exist between two rapidly growing suburban municipalities of the Greater Toronto Area and four cities in northern, eastern, and southwestern Ontario that face the dual challenges of industrial restructuring and an aging population. We also provide a case study involving two of these cities where local leaders actively encourage the in‐migration of seniors from other communities as a strategy for economic development and growth. The findings suggest that local leaders across Ontario generally embrace an age‐friendly view, but acknowledge there will be challenges to meeting the needs of a large older population, especially with regards to health and long‐term care.