Etymology
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plantation (n.)

mid-15c., plantacioun, "action of planting (seeds, etc.)," a sense now obsolete, from Latin plantationem (nominative plantatio) "a planting," noun of action from past-participle stem of *plantare "to plant" (see plant (n.)).

From c. 1600 as "introduction, establishment." From 1580s as "a planting with people or settlers, a colonization;" used historically used for "a colony, an original settlement in a new land" by 1610s (the sense in Rhode Island's Providence Plantations, which were so called by 1640s).

The meaning "large farm on which tobacco or cotton is grown" is recorded by 1706; "Century Dictionary" [1895] defines it in this sense as "A farm, estate, or tract of land, especially in a tropical or semi-tropical country, such as the southern parts of the United States, South America, the West Indies, Africa, India, Ceylon, etc., in which cotton, sugar-cane, tobacco, coffee, etc., are cultivated, usually by negroes, peons, or coolies."

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overseer (n.)

late 14c., "supervisor, superintendent, one who looks over," agent noun from oversee (v.). Specifically, "one who superintends workmen;" especially with reference to slavery, "one who has charge, under the owner or manager, of the work done on a plantation."

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quarters (n.)

"military dwelling place," 1590s, from quarter (n.1) in sense of "portion of a town." As "part of an American plantation where the slaves live," from 1724. The military sense seems to be also the source of quartermaster and it might be behind the phrase give quarter "spare from immediate death" (1610s, often in the negative), on the notion of "provide a prisoner with shelter;" see quarter (n.2).

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planter (n.)

late 14c., plaunter, "one who sows seeds," agent noun from plant (v.). The mechanical sense of "tool or machine for planting seeds" is by 1850. Figurative sense of "one who introduces, establishes, or sets up" is from 1630s. Meaning "one who owns a plantation, the proprietor of a cultivated estate in West Indies or southern colonies of North America" is from 1640s, hence planter's punch (1890). Meaning "a pot for growing plants" recorded by 1959.

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hacienda (n.)
1760, from American Spanish, "an estate or ranch in the country," from Spanish hacienda "landed estate, plantation," earlier facienda, from Latin facienda "things to be done," from facere "to do" (from PIE root *dhe- "to set, put"). For noun use of a Latin gerundive, compare agenda. The owner of one is a hacendado.

The change of Latin f- to Spanish h- is characteristic; compare hablar from fabulari, hacer from facere, hecho from factum, hermoso from formosum. Confusion of initial h- and f- was common in 16c. Spanish; the conquistador is known in contemporary records as both Hernando and Fernando Cortés.
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chaparral (n.)

"dense, low shrub thicket," 1850, American English, from Spanish chaparro "evergreen oak," perhaps from Basque txapar "little thicket," diminutive of sapar "heath, thicket."

In Spain, a chaparral is a bush of a species of oak. The termination al signifies a place abounding in; as, chaparral, a place of oak-bushes, almendral, an almond orchard; parral, a vineyard; cafetal, a coffee plantation, etc., etc.

This word, chaparral, has been introduced into the language since our acquisition of Texas and New Mexico, where these bushes abound. It is a series of thickets, of various sizes, from one hundred yards to a mile through, with bushes and briars, all covered with thorns, and so closely entwined together as almost to prevent the passage of any thing larger than a wolf or hare. [John Russell Bartlett, "Dictionary of Americanisms," 1859]
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grog (n.)
1749, "alcoholic drink diluted with water," supposedly a reference to Old Grog, nickname of Edward Vernon (1684-1757), British admiral who wore a grogram (q.v.) cloak and who in August 1740 ordered his sailors' rum to be diluted. George Washington's older half-brother Lawrence served under Vernon in the Caribbean and renamed the family's Hunting Creek Plantation in Virginia for him in 1740, calling it Mount Vernon. Eventually the word came popularly to mean "strong drink" of any kind. Grog shop "tavern where alcohol is sold by the glass" is from 1790.
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blackface 

also black-face, 1868 (the phrase itself seems not to have been common in print before 1880s) in reference to a performance style, originated in U.S., where (typically) non-black performers used burnt cork or other theatrical make-up to blacken their faces, from black (adj.) + face (n.). The thing itself is older, from the 1830s.

The old-time black face song-and-dance man has disappeared from the stage. At one time no minstrel or variety company was complete without a team of these stage favorites; and who can ever forget their reception at every performance? It made no difference whether they represented the genteel or the plantation negro, they were always welcome, and as a rule were the big feature of the bill. [William E. "Judge" Horton, "About Stage Folks," 1902]
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bowery (n.)

"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]
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cotton-picking (adj.)

as a deprecatory term first recorded in a Bugs Bunny cartoon, but a similar noun cotton-picker meaning "contemptible person" dates to around 1919, perhaps with racist overtones that have faded over the years. Before mechanization, cotton picking was the most difficult labor on a plantation.

I drove out to a number of the farms near Denison and found many very young white children working all day in the hot sun picking and dragging sacks of cotton. In one field the labor corps consisted of one woman and six children, one of them 5 years, one 6 years, one 7 years, one 9 years, and two about 11. The father was plowing. The 5 and 6 year olds worked all day as did the rest. The 7-year-old said he picked 50 pounds a day and the 9 year old 75 pounds. (A good picker averages several hundred a day.) School begins late on account of the cotton picking, but the children nearly all prefer school to the picking. Picking hours are long, hot, and deadly monotonous. While the very young children seem to enjoy it, very soon their distaste for it grows into all-absorbing hatred for all work. ["Field Notes of Lewis W. Hine, Child-Labor Conditions in Texas," report to U.S. Congressional Commission on Industrial Relations, 1916]
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