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Published the same year as his larger view of Boston proper, Bailey composed this view as though he is hovered above Bostons North End and Charlestown looking east across the harbor at East Boston. Using this perspective, he places that community's waterfront, docks, and shipyards prominently in the foreground, emphasizing East Boston's reliance on maritime activities.
At the docks and in the surrounding waters, the artist draws more than 75 sailing vessels and only a few steam-powered vessels, underlining the importance of that community's shipyards in constructing clipper ships and other sailing vessels during the middle of the 19th century. Donald McKay, who would become America's leading designer and builder of clipper ships, had established his shipyard in 1844 in East Boston, along Border Street, between White and Eutaw Streets. In this 1879 view, published two years after McKay retired from the business, his waterfront location is included in the lower left corner of the drawing, but it has been replaced by the Boston Dyewood and Chemical Company. As though symbolic of the clipper ships decline as they competed with the developing steam ship industry, this view includes two inset illustrations in opposing corners on the left, the Dyewood Company, with the hull of an incomplete ship at the adjacent dock, and on the right, the Cunard Steamship Company, also identified as number 3.
Thinly populated until the early 19th century, the area known as East Boston was created by adding land fill around two large islands (Noddles and Breeds) and several smaller islands on the north side of Boston Harbor. The land fill process, which began in the 1830s, is plainly seen in this view, with the basin between the two rail lines portrayed as marshland overlain by a grid of proposed streets. By the middle of the 20th century, the land fill would have extended eastward to encompass Governors Island, adding approximately 1,400 acres to accommodate the construction of Logan Airport.