This article explores the role played by landowners and planners in the development of south-west Cheshire during the period 1750–2000. Decisions made by major landowners and subsequently twentieth-century planners had a continuous and profound effect on settlement patterns and development from the mid-eighteenth century up to the end of the twentieth century. Larger settlements in the area’s more ‘open’ townships increased in size both physically and demographically throughout the period, while smaller settlements in ‘closed’ townships tended to stagnate or decline in these terms. The intervention of major landowners slowed settlement growth and, unlike many parts of the country, settlements in the area showed comparatively little alteration overall between 1750 and 2000. Landowners had both a direct influence on settlement development through the buying and selling of land and an indirect influence through their role in determining the transport infrastructure. The article concludes that patterns established in the eighteenth and nineteenth centuries were perpetuated into the late twentieth and early twenty-first century by a conservative approach to planning which emphasised maintaining the land for agricultural use.