Laid out in 1785 by Thomas Brown, Brownsville was a natural strategic point known then in the western counties as Redstone Old Fort. A major land to water transfer point for the westward journey, it was heavily used by early settlers traveling the Nemacolin Path (Front Street) and, later, the National Road (Market Street). After 1844, a series of locks and dams on the Monongahela River allowed nearly 300,000 passengers a year to set off upriver from Brownsville. Water access made Brownsville a center for boat-building, first for keelboats and later for steamboats. It served the western frontier as a commercial and industrial center during the National Road's heyday. After a rail line between Pittsburgh and Philadelphia opened in 1852, Brownsville's population peaked with just over 2,300 residents; it never reached that level again. Instead, it stagnated for nearly thirty years, dependent on the transport of coal and coke to Pittsburgh's foundries and mills between 1907 and 1930.
Brownsville's earliest buildings are several handsome stone houses, dating from the 1790s. They are located in the six square blocks of the Northside neighborhood, a hilltop section adjacent to the major highway bridge carrying U.S. 40 across the Monongahela River. A brick commercial block built between 1815 and 1840 on the north side of Market Street between 4th and 5th streets is a vernacular version of merchant shops and residences seen often in such seaports as Baltimore. Nine churches (1845 to 1920) reflect the early English, German, and Irish influences in this neighborhood, which survived its time as outfitter to the westward migrants, and its later incarnation as the middle-class residential area after commercial interests moved closer to the river into the area known as “the Neck.” This latter was named when a causeway was built to link the higher ground with the river plain and the bridge crossing Dunlap's Creek. Later, landfill gave the area its present dimensions, and the coal-hauling Monongahela Railway prompted an early-twentieth-century building boom along this lower portion of Market Street.
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