While American colonists knew of the mountains looming less than 200 miles inland from the Atlantic coast, they did not attempt to cross them or penetrate the interior wilderness for over 150 years after Jamestown was founded. Those early colonists found it easier to establish new settlements along the seacoast and follow navigable streams up into the interior.

A few adventuresome frontiersmen, explorers, and surveyors ventured west, including Samuel Stalnaker, who told Dr. Thomas Walker how to find his way through the Cumberland Gap. Daniel Boone started the migration route west over the Wilderness Road in 1773 when he moved his and five other families to Kentucky. George Rogers Clark, who traveled the same road, called Boone's Trace, explored the interior in 1775. Very quickly, they were followed by settlers who began to take the Ohio River west to Warrior's Path, which led them south into the interior. That trickle of early settlers became a steady stream of pioneers whose descendants would continue to migrate west until settlements spanned from coast to coast.

In 1785, as the fledgling country was taking form, the three million citizens of that new nation began hearing more about the rich land available at little cost in what would become Kentucky and Tennessee. Tales of Daniel Boone's excursions and settlements beyond the mountains spread rapidly, kindling the urge in many to take advantage of the easy terms for acquiring land. Other conditions, such as high taxes, crowded conditions in the seaboard states, and the economic difficulties being experienced by nearly everyone following the war, added to the motivation to move west into Kentucky and Tennessee. Some of them west directly to their intended destination, but others spent some time in places along the way or decided not to continue the journey. Knowing the early routes leading from the coastal states to the interior can lead to finding pioneer ancestors who disappear from one location without leaving a public record that mentions their destination.

Routes from Philadelphia and Maryland
People leaving Philadelphia for Kentucky faced an 800 mile journey by way of the Cumberland Gap. They departed Philadelphia and traveled due west to Lancaster, Pennsylvania before turning south to York and Wadkin's Ferry on the Potomac River to reach Martinsburg (presently in Berkeley County, West Virginia). Continuing south, they forged ahead to Winchester (presently in Frederick county, Virginia), where they began to follow the Great Trading Path, a trail that had been used for untold generations by Indian traders. Following that path, they continued down the Shenandoah Valley through New Market and Staunton, and then moved further south across the western end of the James River to Fincastle. From there the path started to angle in a southwesterly direction at Fincastle through Draper's Meadows and on to the outpost called Fort Chiswell.

Fort Chiswell consisted of a crude block-house built in 1758 during the French and Indian War at the junction of the Richmond Road and the Great Trading Path at the headwaters of the New River (presently near the Virginia-North Carolina border in Grayson County, Virginia). The Cumberland Gap was 200 miles away through the roughest and most dangerous part of the journey. The river trip from English's Ferry in the town New River to Fort Chiswell consisted of approximately 30 miles. William Brown, a traveler who set out from Hanover, Virginia en route to Kentucky in 1789 penned the following observations about the journey from New Market to Fort Chiswell:

Crossing Blue Ridge is not bad; there is not more than a small hill with some winding to go over. Neither is the Alleghany Mountain by any means difficult at this gap. There are one or two high hills about New River and Fort Chiswell. The ford of New River is rather bad; therefore we thought it advisable to cross in the ferry-boat. This is generally a good-watered road as far as the Block-house. We waited hereabouts near two weeksfor company, and then set out for the wilderness with twelve men and ten guns, this being thursday, 18th July [1789]. The road from this until you get over Wallen's Ridge generally is bad, some parts of it very much so, particularly about Stock Creek and Stock Creek Ridge. It is a very mountainous country hereabout, but there is some fine land in the bottoms, near the water courses, in narrow slips. It will be but a thin-settled country whenever it is settled.

The Great Trading Path pushed further west to Shelby's Station and across the Holstein and Clinch rivers, then down Powell's Valley to the Cumberland Gap. The valley is formed by Powell Mountain on the southeast and the Cumberland Mountain on the northwest. Continuing with William Brown's commentary:

[The valley] appears to bear from northeast southwestwardly, and is, I suppose, about 100 miles in length, and from ten to twelve miles in bredth (sic). The land generally is good, and is exceeding well-watered country, as well as the country on the Hostein River, abounding with fine springs and little brooks. For about fifty miles, as you travel along the valley, Cumberland Mountain appears to be a very high ridge of white rocks, inaccessible in most places to either man or beast, and affords a wild, romantic prospect. The way through the gap is not very difficult, but from its situation travelers may be attacked in some places, crossing the mountain, by the enemy to a very great disadvantage.

Once through the Cumberland Gap, travelers moved up into Kentucky via the Wilderness Road to Logan's Station, Harrod's Town, Boonesborough, and Boone's Station. Warrior's Path began on the west side of the Cumberland Gap and went northeast to the Ohio River. Others followed the Great Trading Path further south to Fort Loudoun and then followed the Nickajack Trail northwest to where the Chickasaw Trail began at the bend in the Cumberland River. The Chickasaw Trail, later renamed Robert's Road, led south into Tennessee

Four years after Daniel Boone cut a trace (called Boone's Trace) through the Kentucky wilderness in 1779, the Virginia legislature passed an act to provide for the building of a road to accommodate the great numbers of people who were settling in Kentucky in what they considered "great numbers." Provision for building a wagon road did not take place for many years, during which pioneers continued to take the Wilderness Road into Kentucky. According to the first two federal censuses, Kentucky's population had reached 73,000 in 1790 and more than 220,000 in 1800.

Routes from Virginia and North Carolina
Most of the pioneers from Virginia and North Carolina to Kentucky passed through the Cumberland Gap, along with those from Pennsylvania and Maryland. Some travelers took the Great Trading Path to the Wilderness Road, which led into Kentucky and then went as far as the Rockcastle hills where they took the Great Trading Path south to Fort Loudon. From there they continued south to the Nickajack Trail which led northwest to where the Chickasaw Trail began on the bluffs along the Cumberland River (presently Nashville). Eventually, the Knoxville and Nashville Roads offered a more direct path from the Clinch River to Nashville and other points in middle Tennessee. The route took travelers through less difficult terrain than the Wilderness Road and it accommodated large wagons.

Peak Migration Periods
Kentucky experienced its peak migration period between 1775 and 1795, when an abundance of cheap land prevailed. The majority of those early pioneers came primarily from Virginia and secondarily from Pennsylvania. In Virginia, residents of Spotsylvania, Culpeper, Orange, and Madison counties watched their adult children pack up after the Revolution and move west into the triangular area between Cincinnati, Louisville, and Danville. Residents of Russell, Lee, Washington, Montgomery, and Scott counties Virginia went through the Cumberland Gap into northeast Tennessee and southeast Kentucky. Pennsylvanians settled in Bourbon, Nicholas, and Mason counties Kentucky, along with some southwestern Virginia families.

Other Routes West into Kentucky and Tennessee
As more roads were built between 1795 and 1815, other routes into Kentucky and Tennessee absorbed some of the heavy traffic down the Shenandoah Valley and through the Cumberland Gap, including:

Routes from Philadelphia:

Route 1
Forbes Road from Philadelphia to the Ohio River in Pittsburgh.
Down the Ohio River by barge to Cincinnati.
From Cincinnati by barge to the Licking River.
Down the Licking River into the Kentucky interior.

Route 2
Great Valley Road southwest from Philadelphia to Fort Chiswell.
Wilderness Road through the Cumberland Gap to Louisville, Frankfort, and Zane's Trace.
Knoxville Road, beginning south of Fort Chiswell at Josesboro, to Knoxville.
From Knoxville, the Nashville Road led to Nashville, Tennessee.

Route 3
Great Valley Road south to Braddock's Road.
South to Richmond, following the Richmond Road to Fort Chiswell.
Wilderness Road through the Cumberland Gap then northwest to Louisville and Frankfort.
Knoxville Road intersects the road between Fort Chiswell and the Cumberland Gap, leading to Knoxville and Nashville Roads.

Route from Wheeling, Virginia

Zane's Trace from Wheeling southwest to Maysville, situated on the Kentucky side of the Ohio River.
From Marysville Zane's Trace to a branch of the Wilderness Road leading north to Frankfort, Kentucky.
Continuing west to the main Wilderness Road leading North to Louisville.
Continuing west to Fort Gillad in Kentucky's western interior.

Routes from North Carolina:

Route 1
From New Bern on the coast, west on Jonesboro Road through Raleigh and Greensboro.
Jonesboro Road west to Knoxville Road.
Knoxville Road northeast to Jonesboro or west to Knoxville.
Old Walton Road on the south of Knoxville or Nashville Road on the north of Knoxville to Nashville.

Route 2
Following "Route 1" above to Knoxville Road.
Knoxville Road northeast to Wilderness Road.
Wilderness Road northwest to the fork leading to Frankfort or
Wilderness Road past the fork and Zane's Trace to Louisville
West at Zane's Trace to Fr. Gillad.

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