roadway (n.)

Middle English rode, from Old English rad "riding expedition, journey, hostile incursion," from Proto-Germanic *raido (source also of Old Frisian red "ride," Old Saxon reda, Middle Dutch rede, Old High German reita "foray, raid"), from PIE *reidh- "to ride" (see ride (v.)). Also related to raid (n.).

In Middle English it was still, "a riding, a journey on horseback; a mounted raid;" the sense of "an open passage or way for traveling between two places" is recorded from 1590s, and the older senses now are obsolete. "The late appearance of this sense makes its development from sense 1 somewhat obscure," according to OED, which however finds similar evolutions in Flemish and Frisian words. The modern spelling was established 18c.  

The meaning "narrow stretch of sheltered water near shore where ships can lie at anchor" is from early 14c. (as in Virginia's Hampton Roads). In late 19c. U.S. use it is often short for railroad.

On the road "traveling" is from 1640s. Road test (n.) of a vehicle's performance is by 1906; as a verb from 1937. Road hog "one who is objectionable on the road" [OED] is attested from 1886; road rage is by 1988. Road map is from 1786; road trip is by 1950, originally of baseball teams. Old English had radwerig "weary of traveling."

Old English weg "road, path; course of travel; room, space, freedom of movement;" also, figuratively, "course of life" especially, in plural, "habits of life" as regards moral, ethical, or spiritual choices, from Proto-Germanic *wega- "course of travel, way" (source also of Old Saxon, Dutch weg, Old Norse vegr, Old Frisian wei, Old High German weg, German Weg, Gothic wigs "way"), from PIE root *wegh- "to go, move, transport in a vehicle."

From c. 1300 as "manner in which something occurs." Adverbial constructions attested since Middle English include this way "in this direction," that way "in that direction," both from late 15c.; out of the way "remote" (c. 1300). In the way "so placed as to impede" is from 1560s.

From the "course of life" sense comes way of life (c. 1600), get (or have) one's way (1590s), have it (one's) way (1709). From the "course of travel" sense comes the figurative go separate ways (1837); one way or (the) other (1550s); have it both ways (1847); and the figurative sense of come a long way (1922).

Adverbial phrase all the way "completely, to conclusion" is by 1915; sexual sense implied by 1924. Make way is from c. 1200. Ways and means "resources at a person's disposal" is attested from early 15c. (with mean (n.)). Way out "means of exit" is from 1926. Encouragement phrase way to go is short for that's the way to go.