/ Dictionary / Index W Wilderness Road: Meaning and Definition of Find definitions for: Wil'derness Road' Pronunciation: [key] — Amer. Hist. Amer. Hist. a 300-mile (500-km) route from eastern Virginia through the Cumberland Gap into Kentucky, explored by Daniel Boone in 1769 and marked as a trail by him and other pioneers in 1775: a major route for early settlers moving west. Random House Unabridged Dictionary, Copyright © 1997, by Random House, Inc., on Infoplease. wilderness area wild-eyed Related Content Daily Word Quiz: cetacean Analogy of the Day: Today’s Analogy Spelling Bee: Today’s Spelling Bee Frequently Misspelled Words Frequently Mispronounced Words Easily Confused Words Writing & Language