Old English heafod lond "strip of land left unplowed at the edge of a field to leave room for the plow to turn," naturally identified with boundaries; see head (n.) + land (n.). Meaning "high cape, promontory" is from 1520s.
Old English heafod "top of the body," also "upper end of a slope," also "chief person, leader, ruler; capital city," from Proto-Germanic *haubid (source also of Old Saxon hobid, Old Norse hofuð, Old Frisian haved, Middle Dutch hovet, Dutch hoofd, Old High German houbit, German Haupt, Gothic haubiþ "head"), from PIE root *kaput- "head."
Modern spelling is early 15c., representing what was then a long vowel (as in heat) and remained after pronunciation shifted. Of rounded tops of plants from late 14c. Meaning "origin of a river" is mid-14c. Meaning "obverse of a coin" (the side with the portrait) is from 1680s; meaning "foam on a mug of beer" is first attested 1540s; meaning "toilet" is from 1748, based on location of crew toilet in the bow (or head) of a ship.
Synechdochic use for "person" (as in head count) is first attested late 13c.; of cattle, etc., in this sense from 1510s. As a height measure of persons, from c. 1300. Meaning "drug addict" (usually in a compound with the preferred drug as the first element) is from 1911.
To be over (one's) head "beyond one's comprehension" is by 1620s. To give head "perform fellatio" is from 1950s. Phrase heads will roll "people will be punished" (1930) translates Adolf Hitler. Head case "eccentric or insane person" is from 1966. Head game "mental manipulation" attested by 1972.
Old English lond, land, "ground, soil," also "definite portion of the earth's surface, home region of a person or a people, territory marked by political boundaries," from Proto-Germanic *landja- (source also of Old Norse, Old Frisian Dutch, Gothic land, German Land), perhaps from PIE *lendh- (2) "land, open land, heath" (source also of Old Irish land, Middle Welsh llan "an open space," Welsh llan "enclosure, church," Breton lann "heath," source of French lande; Old Church Slavonic ledina "waste land, heath," Czech lada "fallow land"). But Boutkan finds no IE etymology and suspects a substratum word in Germanic,
Etymological evidence and Gothic use indicates the original Germanic sense was "a definite portion of the earth's surface owned by an individual or home of a nation." The meaning was early extended to "solid surface of the earth," a sense which once had belonged to the ancestor of Modern English earth (n.). Original senses of land in English now tend to go with country. To take the lay of the land is a nautical expression. In the American English exclamation land's sakes (1846) land is a euphemism for Lord.
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Definitions of headland from WordNet
a natural elevation (especially a rocky one that juts out into the sea);