Middletown

Old English middel, "equally distant from extremes or limits; intermediate," from Proto-West Germanic *midla- (source also of Old Frisian middel, Old Saxon middil, Middle Low German, Dutch middel, Old High German mittil, German mittel), from Proto-Germanic *medj, from PIE root *medhyo- "middle."

Middle finger "the third finger" (counting the thumb as the first)  so called from late Old English. Middle school is attested from 1838, originally "middle-class school, school for middle-class children;" the sense in reference to a school for grades between elementary and high school is from 1960. Middle management, the level below senior management, is by 1941.

Middle-of-the-road in the figurative sense is attested from 1894, originally political; edges of a dirt road can be washed out and thus are less safe, but the notion here probably is of the middle as "less exposed to ambush." Middle way in the figurative sense of "path of moderation" is from c. 1200. Middle ground as "place of moderation or compromise between extremes" is by 1961. Middle-sized "of medium size" is by 1620s.

In U.S. history, the Middle States (1784) were those between New England and the South (New York, New Jersey, Pennsylvania, Delaware). Middle America for "the 'silent majority,' the generally conservative middle class regarded as a homogeneous group" is by 1968.

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.