Transportation plays a critical role in the dairy industry because fluid milk must be handled and delivered rapidly between cow and consumer, due to its highly perishable nature. In this paper, I ask how the development of the transportation industry has affected New York State farmers over the past two centuries, and how this has directly impacted farmers in the state today. As the mode of milk delivery changed from carts to railroads – and eventually to tanker trucks – the spatial arrangement of farms, the volume of milk production, and the intensity of resource use were altered as well. Dealers entered into farmers’ relationship with environmental and market conditions as the region of fluid milk production expanded – creating an industry that looked to growth, no matter what the demand or cost, as inevitable and guaranteed. I argue that the way the transportation industry evolved over the past two centuries has created economies of scale in the dairy industry that enabled milk to become a commodity and encouraged the development of large-scale dairy farms in New York State, making it difficult for small farms to compete.