Oceans and waterways were the superhighways of the past, moving both people and goods. By the mid-nineteenth century sailing became more than just a mode of transport—it developed into a pastime. Trains and industrialization moved transportation to land, and simultaneously leisure time increased and urban Americans sought rest and relaxation through outdoor activities on our lakes, rivers, and seacoast. With these cultural changes boating blossomed as a sport and recreational activity. The maritime collection of the Wadsworth reveals this transformation of Connecticut’s waterways from the thoroughfare for commercial merchant ships to pleasure cruises and competitive racing.