The forces that shaped the Toano Commercial Historic District’s initial development extend back to 1881 and construction of the Chesapeake & Ohio (C&O) Railroad’s “Peninsula Extension,” which boosted the prosperity of Toano and its environs through the movement of goods, people, and ideas; and allowed the C&O to traverse the entire length of Virginia. Meanwhile, by improving access to northern cities, the railroad engendered a new, market-oriented agriculture in James City County centered on truck farming. This revolution created two new manufacturing operations—a barrel factory and a cannery—in Toano to facilitate the shipment of produce to urban markets. Starting ca. 1903, construction of a group of new commercial buildings, including a bank, in Toano demonstrates the vibrancy of local economic activity at the time. Although the railroad tracks and depot were relocated in 1906, today the Toano Commercial Historic District continues to reflect the railroad’s impact on the community’s physical development.