1767, of roads, "lying or directed across fields or open country," from cross- + country, or a shortening of across-country. Of flights, from 1909. As a noun, "outdoor distance running as a sport," by 1956.
word-forming element typically representing cross as a noun, adverb (cross-examine), adjective (crossbar), and in many words a confluence of them. "There is no distinct line of division between cross as an adjective and cross as a prefix. As a prefix, it often represents the adv. cross, or the prep. cross, across." [Century Dictionary]
mid-13c., "(one's) native land;" c. 1300, "any geographic area," sometimes with implications of political organization, from Old French contree, cuntrede "region, district, country," from Vulgar Latin *(terra) contrata "(land) lying opposite," or "(land) spread before one," in Medieval Latin "country, region," from Latin contra "opposite, against" (see contra-). The native word is land.
Also from c. 1300 as "area surrounding a walled city or town; the open country." By early 16c. the word was applied mostly to rural areas, as opposed to towns and cities. Meaning "inhabitants of a country, the people" is from c. 1300.
INTERVIEWER [Steve Rossi]: "Would you say you're the best fighter in the country?
PUNCH-DRUNK BOXER [Marty Allen]: "Yeah, but in the city they murder me."
As an adjective from late 14c., "peculiar to one's own country (obsolete); by 1520s as "pertaining to or belonging to the rural parts of a region," typically with implications of "rude, unpolished."
Country air "fresh air" is from 1630s. First record of country-and-western as a music style is by 1942, American English. Country music is by 1968. Country club "recreational and social club, typically exclusive, located in or near the country" is by 1886. Country mile "a long way" is from 1915, American English. Country-mouse is from 1580s; the fable of the mouse cousins is as old as Aesop. Country road "road through rural regions" is from 1873.