This paper explores the dynamics of change and development in rural-urban environments. Urbanization in the context of rural and regional environments can be grouped into two categories: rural urbanization and urbanization. Rural urbanization is a product of a range of push and pull factors that result in people from rural regional areas moving to cities and small and intermediate towns. Many have little choice but to live in small scattered urban settlements in peri-urban areas of cities and towns, or along urban transportation corridors. Urbanization is a counter-cyclical process to rural urbanization, comprising a small but increasing flow of urban wealthy and diaspora who are buying back and developing in predominantly rural regional towns. This paper commences with a series of definitions that set the context for the discussion of the dynamics and change in the geography and function of small and intermediate towns. It discusses some current and emerging factors driving people from the land to Small and intermediary towns. Factors like expatriate, foreign and company land grabs and purchases, technological changes in agriculture production, logistics, quality assurance, and markets; rural debt, impacts of remittances on local economies; climate change impacts and the dynamics of labor markets are transforming the landscapes of rural areas in all countries. Small and intermediary cities offer opportunities for subsistence living for a growing marginalized population in the transition from rural to urban living. How to manage the development of these towns, which are the front line of rural-urban migration, in rapidly urbanizing economies is proving to challenge. Many are becoming poverty traps for people leaving the land either by choice or force. Most cannot go back, nor do not have the capacity or desire to migrate to larger cities. The paper will explore what national and local governments’ policy responses could be to improve the sustainability of rural urbanization and development in small and intermediate towns, with a focus on developing economies.