[8] In the 17th century, the road branched off Broadway north of Fort Amsterdam at the tip of Manhattan to the homestead of Peter Stuyvesant, director-general of New Netherland.

In 1654, the Bowery's first residents settled in the area of Chatham Square; ten freedmen and their wives set up cabins and a cattle farm there.

[14] In her Journal of 1704–05, Sarah Kemble Knight describes the Bowery as a leisure destination for residents of New York City in December: Their Diversions in the Winter is Riding Sleys about three or four Miles out of Town, where they have Houses of entertainment at a place called Bowery, and some go to friends Houses who handsomely treat them.

[...] I believe we mett 50 or 60 slays that day – they fly with great swiftness and some are so furious that they'le turn out of the path for none except a Loaden Cart.

[15]By 1766, when John Montresor made his detailed plan of New York,[16] "Bowry Lane", which took a more north-tending track at the rope walk, was lined for the first few streets with buildings that formed a solid frontage, with market gardens behind them; when Lorenzo Da Ponte, the librettist for Mozart's Don Giovanni, The Marriage of Figaro, and Così fan tutte, immigrated to New York City in 1806, he briefly ran one of the shops along the Bowery, a fruit and vegetable store.

In 1766, straight lanes led away at right angles to gentlemen's seats, mostly well back from the dusty "Road to Albany and Boston", as it was labeled on Montresor's map; Nicholas Bayard's was planted as an avenue of trees.

James Delancey's grand house, flanked by matching outbuildings, stood behind a forecourt facing Bowery Lane; behind it was his parterre garden, ending in an exedra, clearly delineated on the map.

The Bull's Head Tavern was noted for George Washington's having stopped there for refreshment before riding down to the waterfront to witness the departure of British troops in 1783.

Leading to the Post Road, the main route to Boston, the Bowery rivaled Broadway as a thoroughfare; as late as 1869, when it had gained the "reputation of cheap trade, without being disreputable" it was still "the second principal street of the city".

The street gained in respectability and elegance, becoming a broad boulevard, as well-heeled and famous people moved their residences there, including Peter Cooper, the industrialist and philanthropist.

[18] Theodore Dreiser closed his tragedy Sister Carrie, set in the 1890s, with the suicide of one of the main characters in a Bowery flophouse.

[21] Gay subculture was more highly visible there and more integrated into working-class male culture than it was to become in the following generations, according to historian George Chauncey.

[22] Prohibition eliminated the Bowery's numerous saloons: One Mile House, the "stately old tavern... replaced by a cheap saloon"[23] at the southeast corner of Rivington Street, named for the battered milestone across the way,[24] where the politicians of the East Side had made informal arrangements for the city's governance,[25][26] was renovated for retail space in 1921, "obliterating all vestiges of its former appearance", The New York Times reported.

Aside from cheap clothing stores that catered to the derelict and down-and-out population of men, commercial activity along the Bowery became specialized in used restaurant supplies and lighting fixtures.

[32] At least 75 tenants were displaced from 83 to 85 Bowery in January 2018 in frigid temperatures due to long-overdue repairs that needed to be made.

[39] New York magazine claims that while this street blends in with neighboring Chinatown, the area is filled with Vietnamese restaurants.

[41] Its 1893 headquarters building at 130 Bowery is an official New York City designated landmark,[42] as is the 1920s domed Citizens Savings Bank.

Seasonal murals have appeared on the wall curated and organized in collaboration with The Hole, NYC, an art gallery in SoHo run by former Deitch Projects directors Kathy Grayson and Meghan Coleman.

This was followed by a mural by the Brazilian twin-brother duo Os Gêmeos, which they dedicated to artist Dash Snow, who had recently died from a drug overdose; this was presented from July 2009 to March 2010.

[46] Other artists to have murals presented include the twins How & Nosm (2012), Crash (2013), Martha Cooper (2013), Revok and Pose (2013), Swoon (2014), and Maya Hayuk.

It was founded by Bob Holman, owner of the building and former Nuyorican Poets Café Poetry Slam MC (1988–1996).

This spawned a full-blown scene of new bands (Talking Heads, Blondie, edgy R&B-influenced Mink DeVille, rockabilly revivalist Robert Gordon, and others) performing mostly original material in a mostly raw and often loud and fast attack.

CBGB closed on October 31, 2006, after a long battle by club owner Hilly Kristal to extend its lease.