Etymology
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shire (n.)
Old English scir "administrative office, jurisdiction, stewardship, authority," also in particular use "district, province, country," from Proto-Germanic *skizo (source also of Old High German scira "care, official charge"). Ousted since 14c. by Anglo-French county. The gentrified sense is from The Shires (1796), used by people in other parts of England of those counties that end in -shire; sense transferred to "hunting country of the Midlands" (1860).
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town (n.)
Old English tun "enclosure, garden, field, yard; farm, manor; homestead, dwelling house, mansion;" later "group of houses, village, farm," from Proto-Germanic *tunaz, *tunan "fortified place" (source also of Old Saxon, Old Norse, Old Frisian tun "fence, hedge," Middle Dutch tuun "fence," Dutch tuin "garden," Old High German zun, German Zaun "fence, hedge"), an early borrowing from Celtic *dunon "hill, hill-fort" (source also of Old Irish dun, Welsh din "fortress, fortified place, camp," dinas "city," Gaulish-Latin -dunum in place names), from PIE *dhu-no- "enclosed, fortified place, hill-fort," from root *dheue- "to close, finish, come full circle" (see down (n.2)).

Meaning "inhabited place larger than a village" (mid-12c.) arose after the Norman conquest from the use of this word to correspond to French ville. The modern word is partially a generic term, applicable to cities of great size as well as places intermediate between a city and a village; such use is unusual, the only parallel is perhaps Latin oppidium, which occasionally was applied even to Rome or Athens (each of which was more properly an urbs).

First record of town hall is from late 15c. Town ball, version of baseball, is recorded from 1852. Town car (1907) originally was a motor car with an enclosed passenger compartment and open driver's seat. On the town "living the high life" is from 1712. Go to town "do (something) energetically" is first recorded 1933. Man about town "one constantly seen at public and private functions" is attested from 1734.
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small-town (adj.)
"unsophisticated, provincial," 1824, from noun phrase, from small (adj.) + town.
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cross-town (adj.)

also crosstown, "lying, leading, or going across town," 1865, in reference to New York City street railways, from cross- + town.

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Shropshire 
shortened form of the old spelling of Shrewsbury + shire.
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sheriff (n.)
late Old English scirgerefa "representative of royal authority in a shire," from scir (see shire) + gerefa "chief, official, reeve" (see reeve). As an American county official, attested from 1660s; sheriff's sale first recorded 1798. Sheriff's tooth (late 14c.) was a common name for the annual tax levied to pay for the sheriff's victuals during court sessions.
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Berkshire 
Old English Bearrocscir (893), from an ancient Celtic name meaning "hilly place" + Old English scir "shire, district."
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county (n.)

mid-14c., "a shire, a definite division of a country or state for political and administrative purposes," from Anglo-French counte, from Late Latin comitatus "jurisdiction of a count," from Latin comes (see count (n.1)). It replaced Old English scir "shire."

From late 14c. as "the domain of a count or earl." County palatine, one distinguished by special privileges (Lancaster, Chester, Durham) is from mid-15c. County seat "seat of the government of a county" is by 1848, American English.

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hometown (n.)
also home-town, 1879, from home (n.) + town.
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shantytown (n.)
also shanty town, 1836, from shanty (n.1) + town.
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