roadster (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 -istre, from Proto-Germanic *-istrijon, feminine agent suffix used as the equivalent of masculine -ere (see -er (1)). Also used in Middle English to form nouns of action (meaning "a person who ...") without regard for gender.

The genderless agent noun use apparently was a broader application of the original feminine suffix, beginning in the north of England, but linguists disagree over whether this indicates female domination of weaving and baking trades, as represented in surnames such as Webster, Baxter, Brewster, etc. (though modern spinster probably carries an originally female ending).

Also compare whitester "one who bleaches cloth;" kempster (c. 1400; Halliwell has it as kembster) "woman who cleans wool." Chaucer ("Merchant's Tale") has chidester "an angry woman" (the 17c. had scoldster). Also compare Middle English shepster (late 14c.) "dressmaker, female cutter-out," literally "shapester," sleestere (mid-15c.) "murderess, female killer" ("slay-ster"). Sewster "seamstress" (Middle English seuestre, late 13c. as a surname, also used of men) is still in Jonson but was obsolete or provincial after 17c. In Modern English, the suffix has been productive in forming derivative nouns (gamester, roadster, punster, rodster "angler," etc.).