"farm, plantation," from Dutch bowerij "homestead farm" (from the same source as bower); a Dutch word probably little used in America outside New York, and there soon limited to one road, The Bowery, that ran from the built-up part of the city out to the plantations in middle Manhattan, attested from 1787; the city's growth soon overran it, and it was by 1840 a commercial district notorious for squalor, rowdiness, and low life. The Bowery boy as an American comic type had a heyday in the 1850s and again around 1900.
Bowery Boy, the typical New York tough of a generation or two ago, named from the street which he chiefly affected .... He rather prided himself on his uncouthness, his ignorance, and his desperado readiness to fight, but he also loved to have attention called to his courage, his gallantry to women, his patriotic enthusiasm, and his innate tenderness of heart. A fire and a thrilling melodrama called out all his energies and emotions. [Walsh, 1892]