14c. as a present-participle adjective from roll (v.), "that turns over and over, moving by means of rolling." The meaning "moving on wheels or as if on wheels" is by 1560s. Of thunder, etc., "making continuous noise," 1650s. The sense of "waving, undulating," of prairie land, etc., is from 1819. The meaning "staggered, rotating," of strikes, blackouts, etc., is by 1961.
From mid-15c. as a verbal noun. Rolling-pin "cylindrical piece of wood, etc., with a handle at each end, with which dough, etc. are reduced to proper thickness," is recorded from late 15c. Rolling-paper for cigarettes, etc., is by 1969. Rolling stock "wheeled vehicles on a railroad" (locomotives, carriages, etc.) is by 1853.
The rollyng stone neuer gatherth mosse. [John Heywood, "A dialogue conteinying the nomber in effect of all the proverbes in the Englishe tongue," 1546]
Hence figurative use of rolling stone, of persons, "a rambler, a wanderer" (1610s).