/ Dictionary / Index O Overland Trail: Meaning and Definition of Find definitions for: O'ver•land Trail' Pronunciation: (ō'vur-land", -lund), [key] — U.S. Hist. U.S. Hist. any of various routes traveled by settlers from the Missouri River to Oregon and California beginning in the 1840s. Cf. Random House Unabridged Dictionary, Copyright © 1997, by Random House, Inc., on Infoplease. overland stage overlap Related Content Daily Word Quiz: procrastinate Analogy of the Day: Today’s Analogy Spelling Bee: Today’s Spelling Bee Frequently Misspelled Words Frequently Mispronounced Words Easily Confused Words Writing & Language