Braddock’s Road was the first road to cross the Appalachian mountain range. “In early 1755, the British General, Edward Braddock, began supervising the construction of a wagon road through the wilderness areas of Maryland and Pennsylvania following routes laid out by George Washington... The road was successfully completed. However, due to some poor military tactics, Braddock failed in his military mission.” (William Dollarhide, ''Map Guide to American Migration Routes'', Bountiful, Utah: AGLL, Inc., 1997, 10.)
In 1758 while it was still necessary for the British to advance on Fort Duquesne, the British forces were commanded by General John Forbes. Instead of using Braddock’s Road again, Forbes chose to build a new road further north and sweep down on the French by surprise. But once the road was completed and Forbes arrived with his troops, he discovered that the French had abandoned the fort. (William Dollarhide, ''Map Guide to American Migration Routes'', 11.) Finding it deserted, he renamed it Fort Pitt after his commanding officer; it became known soon as Pittsburgh.
=== Great Wagon Road ===
Great_Wagon_Road-Philadelphia.jpg|center]]“The Philadelphia or Great Wagon Road began its history as ''the Warriors’ Path'', an ancient Indian highway that was used by Iroquois tribesmen of the north to go south to trade, hunt, and make war. When the colonists took over, it extended 800 miles from Philadelphia in the north down through South Carolina in the south, and was the only route of travel at that time.” (Merlin C. and Eva M. Finnell, “''Migration Trails of the Eastern United States'',” 55.)
Tens of thousands used this road, beginning in colonial times and continuing long after. It carried more traffic than all the other early American roads put together.
Fort Chiswell guarded the crossroads where a trunk route crossed over the New River and the Blue Ridge beyond, to Winston-Salem and the Upper Road. The Richmond Roa, ran from Richmond, Virginia, southwest to Fort Chiswell, providing travelers access to the Wilderness Road into Kentucky or north through the Shenandoah Valley.
=== Cumberland Gap and the Wilderness Road ===
Cumberland_Gap_and_Wilderness_Road.jpg|center]]The Cumberland Gap is a natural break in the Appalachian Mountain range (through the Allegheny Mountains), first used by hunting and war parties of rival Indian tribes north of the Ohio River and south of the mountains. In 1750, Dr. Thomas Walker discovered this gap, first called Cave Gap but later named Cumberland Gap. During that same year, Christopher Gist crossed the whole of Kentucky to the Miami River. In 1769 Daniel Boone reached the Cumberland Gap and passed into the Blue Grass hunting ground of both the northern and southern Indian tribes. Reports of this fertile region attracted land-hungry pioneers.
Although illegal under the terms of the Proclamation of 1763, Judge Richard Henderson of North Carolina in 1775 organized the Transylvania Company to buy land from the Indians to sell to white settlers. Next, the Transylvania Company sent Daniel Boone and thirty woodsmen to mark off a trail from the eastern settlements through the Cumberland Gap and down the Kentucky River to the Ohio, a route which later took the name Wilderness Road. Boone established Boonesborough, a small fort on the Kentucky River, near the present city of Lexington.
In the early years, the Wilderness Road was simply a crude trail. Only pack teams could cross the mountains. Pioneers coming from Pennsylvania, Maryland, Virginia, and the Carolinas before 1796 found it necessary to unload their Conestoga wagons at Sapling Grove and pack their belongings on horses. They lashed huge baskets and bundles of clothing, bed furnishings and household articles upon packhorses. Children perched on top, or rode in front and behind their mothers. The older boys and men who did not have mounts had to trudge along on foot. A caravan of pack horses and people on foot sometimes stretched out as far as three miles along the trail. Professional packhorse men made it a business to hire out to settlers or merchants for transporting supplies through the wilderness. They objected to road improvements, saying it would drive them out of business. Nevertheless, changes came about and swarms of people crossed through the Gap into Kentucky and beyond.
=== Other Roads/Trails ===
Roads forked off from one another, connected with one another, paralleled one another, and not infrequently carried alternative names. This adds to the confusion but also points to a fact of major importance: migration paths are not totally predictable! Look for maps showing early American roads, some of which were no more than footpaths, others improved and used for many years.