The increasing importance of large cities (metropolises) poses a range of challenges to the socio-economic functions of the rural and agricultural areas around them. One such challenge is pressure exerted on family-run farms to abandon agricultural activity and on people engaged in such activity to shift to other sectors. This may be a hindrance to successful succession on family farms. The aim of this paper is to present spatial variation in generational changes in farms located around large cities (metropolises) in Poland and to assess the factors affecting the scale of such changes. Special attention was paid to the importance of the location of farms relative to large cities. One innovative feature of the approach presented was to conduct an analysis of generational changes in the agricultural sector at the supra-local level along with an attempt to quantify the impact of large urban centers on that process. The empirical material based on which the conclusions were formulated included official statistics data and information made available by an institution engaged in the implementation of agricultural policy programs financed from European Union (EU) funds, i.e., young farmer payments (Common Agricultural Policy (CAP) pillar I) and measures “Setting up of young farmers” and “Early retirement” (CAP Pillar II). In the executed study, methods of descriptive and multivariate statistics, including regression trees, were used. It was found that socio-economic (exogenous) factors had a significant statistical impact on generational changes in farms. In areas with an attractive labor market and a high level of urbanization, a successful generational shift in farms occurred less often. Nonetheless, generational changes in the agriculture of the analyzed areas were relatively most strongly determined by endogenous factors linked with the economic potential of the farm. Farm characteristics (area of agricultural land and economic size) and the characteristics of managers, including in particular their education, were found to be more important than exogenous factors. In areas where large and economically strong farms dominated and the level of education among farmers was relatively high, generational changes were faster compared to other areas.