Shoemaking was a popular trade in the 1860s. The census for that decade lists 221 boot and shoe makers in eastern Canada West, of which 141 were a single employee working in his own home or an adjacent shop. In smaller communities and in the rural areas, shoe making remained almost entirely handwork. A shoemaker needed only a small set of tools, a series of lasts (wooden forms) and leather hides to set himself up in business. A few shoemakers traveled door to door soliciting business, taking measurements and then making up the shoes in their own shops or homes. A good pair of men's shoes took one or two days to complete. A pair of boots took a little longer.

Shoemakers took exception to being called cobblers. Cobbling refers to a less skilled tradesman who was only able to repair shoes. Cordwaining was an old-fashioned term for shoe making but the term was not in common usage in the 1860s. Most shoemakers repaired shoes as well as made new ones for customers.

By mid-century, shoe and boot makers, and also other tradesmen, were feeling the pressure of competition from factory-made products. Shoe factories in larger urban centers were producing ready-made footwear that was sold in most general stores, and in urban shoe stores in Montreal and Toronto. Manufacturers often located their factories near tanneries and cross-ownership made the business more profitable. In the rural areas, the local shoemaker could order supplies directly from a local tannery or even through the local general store.

Current research suggests that shoemakers during the 19th century in Upper Canada were exclusively men. There is some census evidence that women were employed in urban shoe factories as well as younger boys.

Our shoemaker at Upper Canada Village works in a small log home on Church Street. The location is identified by a large wooden boot hanging above the door, a common business symbol at that time. Our shoemaker makes primarily men's brogues, a common style of work shoe during the mid-nineteenth century. Visitors can see, touch and learn about how these straight-lasted, wooden pegged work shoes in their various stages in their construction.