A halftime report for Canada’s cities over a 200-year span (about seven generations) suggests two distinct halves. In the first half, Canada saw unprecedented and unmatched economic growth, an average annual 2.7% increase in GDP from 1920 to 2020. Economic growth in the second half, 2020–2120, however, will likely be below one percent. This is an enormous difference, compounded by higher levels of debt, a much less benign climate, and growing geopolitical tensions. Future Canadians may not be placated by the fact they are luckier than most of the rest of the world if compared to previous generations their quality of life is declining. Because of their high per capita resource use, Canadians are well-positioned to lead the shift to sustainability that will arrive in lockstep with the energy transition and post-peak population (~ 2080). Key trends for Canadian cities include: (i) severity of global climate impacts and scale of resulting climate migrants and refugees; (ii) significant variability in Canadian climate beyond 2050; (iii) enhanced productivity, overall well-being and the ability to attract and keep immigrants; (iv) the degree of social unrest and local and international agitation, especially in cities; (v) possible claims on Canadian sovereignty, geopolitical tensions, especially from shifting locus of economic activity—from OECD-member countries to Asia (East and South) and eventually Africa; (vi) continued strength of USA and amicable tri-lateral relations, within USMCA framework or subsequent; (vii) infrastructure and provisions of urban services vis-a-vis climate change, staffing capabilities, aging facilities and maintenance; (viii) peak resource use (dates and magnitude), including oil and gas production post-2030; (ix) resilience and climate adaptation, especially of major cities and large-scale infrastructure; geopolitical tensions and shifts in energy and material supply chains; and (x) impact from possible low-likelihood, high-impact events such as geomagnetic storms, earthquakes, and pandemics.