Question: Peter Hackett was born in approximately 1763 or 1764 in the English colony of Virginia, he was a part of the broad Scotch-Irish migration along where, which was one of two principal routes used by colonial and early national era settlers to reach Kentucky from the East?

Context paragraphs:
Indian massacre of 1622: The Indian Massacre of 1622 took place in the English Colony of Virginia, in what is now the United States, on Friday, 22 March 1622.  John Smith, though he had not been in Virginia since 1609 and was not a firsthand eyewitness, related in his "History of Virginia" that braves of the Powhatan "came unarmed into our houses with deer, turkeys, fish, fruits, and other provisions to sell us".  The Powhatan grabbed any tools or weapons available and killed all English settlers they found, including men, women, and children of all ages.  Chief Opechancanough led a coordinated series of surprise attacks by the Powhatan Confederacy that killed 347 people, a quarter of the English population of the Virginia colony.

Westervelt massacre: The Westervelt massacre, also known as the Westerfield massacre, was an indigenous attack on a caravan of Dutch frontier settlers that occurred during the American Revolutionary War around 3:00 am on June 27, 1780 in Kentucky County, Virginia, the present day state of Kentucky.  It remains one of the largest massacres in Kentucky state history.  The settlers were traveling southeast from Low Dutch Station to Harrod's Town.  The settler relocation was in part a reaction to British Captain Henry Bird's invasion of Kentucky.  The area immediately east of Low Dutch Station had been overrun with British allied Indians.  Harrod's Town was fortified and a move south would lead the settlers away from Captain Bird's invading army from the north.  The caravan was ambushed in a surprise attack, during the night, after a day's travel of twelve miles.  The exact location of the massacre is not definitively known.  However, it is likely to have occurred at Floyd's Fork and Broad Run.  The caravan was formed by Jacobus Westervelt and consisted of forty-one settlers from ten different families.  Ten of the seventeen settlers killed were members of the Westervelt family.  The victims included men, women, and children.  The Indians responsible for the massacre were allied to the British and received ₤5 for each victim's scalp cut off and returned to the British authorities.  The Indians were thus awarded ₤85 by the British for massacring the Dutch settlers.  The Westervelt Massacre had a chilling effect on the region.  A number of settlers from Low Dutch Station joined Colonel George Rogers Clark's militia after the massacre.

O. C. Hackett: Oliver Cromwell Hackett was born March 29, 1822 in Scott County, Kentucky.  His father was John Hackett, and his grandfather was noted Kentucky frontiersman and militiaman of the American Revolution, Peter Hackett.  John Hackett moved the family, including young O. C., from Kentucky to Coles County, Illinois in 1835.  O. C. Hackett married Ellen Roxanne (Wyeth) on March 14, 1854.  O. C.'s children included Frederick W. Hackett.  O. C. died April 8, 1905 in Tuscola, Illinois.  Family legend holds that Abraham Lincoln stayed at the Hackett farm near Charleston Illinois before or after the 4th of the Lincoln-Douglas debates of 1858.

History of Virginia: The History of Virginia begins with documentation by the first Spanish explorers to reach the area in the 1500s, when it was occupied chiefly by Algonquian, Iroquoian, and Siouan peoples.  After a failed English attempt to settle Virginia in the 1580s by Walter Raleigh , permanent English settlement began in Virginia with Jamestown, Virginia, in 1607.  The Virginia Company colony was looking for gold but failed and the colonists could barely feed themselves.  The famine during the harsh winter of 1609 forced the colonists to eat leather from their clothes and boots and resort to cannibalism.  The colony nearly failed until tobacco emerged as a profitable export.  It was grown on plantations, using primarily indentured servants for the intensive hand labor involved.  After 1662, the colony turned black slavery into a hereditary racial caste.  By 1750, the primary cultivators of the cash crop were West African slaves.  While the plantations thrived because of the high demand for tobacco, most white settlers raised their families on subsistence farms.  Warfare with the Virginia Indian nations had been a factor in the 17th century; after 1700 there was continued conflict with natives east of the Alleghenies, especially in the French and Indian War (1754-1763), when the tribes were allied with the French.  The westernmost counties including Wise and Washington only became safe with the death of Bob Benge in 1794.

Maryland Day: Maryland Day is a legal holiday in the U.S. state of Maryland.  It is observed on the anniversary of the March 25, 1634, landing of the first European settlers in the Province of Maryland, the third English colony to be settled in British North America.  On this day settlers from ""The Ark"" and the smaller ""The Dove"" first stepped foot onto Maryland soil, at St. Clement's Island in the Potomac River.  The settlers were about 150 in number, departed from Gravesend on the Thames River downstream from London.  Three Jesuit priests were collected from Cowes on the Isle of Wight in England where they avoided having to give the oath of allegiance and supremacy to the King.  The colony's grant was renewed to Cecil Calvert, 2nd Baron Baltimore, (1605-1675), two years prior by Charles I of England, after first being given to his father Sir George Calvert, 1st Baron Baltimore, (1574-1632), along with the title of "Lord Baltimore", and a first grant in Acadia, in Newfoundland, (modern Canada), (title named after lands and town Baltimore, in Ireland) who had served the King in many official and personal capacities as Secretary of State, 1619-1625 (despite his conversion to Roman Catholicism).  In thanksgiving for the safe landing, Jesuit Father Andrew White celebrated the Mass for the colonists led by the younger brother of Lord Baltimore, Leonard Calvert, (1606-1647), who served as the first governor, and perhaps for the first time ever in this part of the world on the first landing at Blackistone Island, later known as St. Clement's Island off the northern shore of the Potomac River, which was the new border between the new colony and the earlier English settlements in Virginia) and erected a large cross.  The landing coincided with the Feast of the Annunciation, a holy day honoring Mary, and the start of the new year in England's legal calendar (prior to 1752).  Maryland Day on 25 March celebrates the 1634 landing at St Clements.  Later the colonists and their two ships sailed further back down river to the southeast to settle a capital at St. Mary's City near the point where the Potomac flows into the Chesapeake Bay.

Peter Hackett: Peter Hackett was born in approximately 1763 or 1764 in the English colony of Virginia.  It is believed that Peter was the son of Thomas Hackett, likely of Montgomery County, Virginia.  As a boy Peter was bonded out to Captain James Estill, in approximately 1771, and was a part of the broad Scotch-Irish migration along the Wilderness Road through the Cumberland Gap from Virginia into what later became known as Kentucky in the late 18th century.  In 1779 he was a resident of Boonesborough, one of the first English-speaking settlements beyond the Appalachian Mountains, and lived there until 1780.  Early residents of Boonesborough included Daniel Boone, James Estill, Joseph Proctor, Nicholas Proctor, Adam Caperton, David Lynch, John Colefoot, John Moore, George Robertson, Thomas Miller, Reuben Proctor, Thomas Warren, Peter Hackett, and Thomas Watson.  In 1780 Hackett helped establish Estill's Station, Kentucky, and lived there until about 1788.

True Reportory: True Reportory is the short-title of a 24,000 word narrative of early American colonial literature, "A true reportory of the wracke, and redemption of Sir Thomas Gates Knight; vpon, and from the Ilands of the Bermudas: his coming to Virginia, and the estate of that Colonie then, and after, vnder the gouernment of the Lord La Warre, Iuly 15.  1610".  The author William Strachey was a passenger on the "Sea Venture", the flagship of the supply fleet that sailed to the English colony of Virginia from Plymouth in June 1609.  During a hurricane it wrecked off the coast of Bermuda, where the survivors built two pinnaces, "Patience" and "Deliverance" to continue the journey.  They arrived in Jamestown in May 1610 and found the colony suffering from famine and Indian attacks that had reduced the 600 colonists to fewer than 70.  "True Reportory" is Strachey's account of these incidents, first published in 1625 in an anthology of new world colonial literature assembled by Samuel Purchas.

Wilderness Road: The Wilderness Road was one of two principal routes used by colonial and early national era settlers to reach Kentucky from the East.  Although this road goes through the Cumberland Gap into southern Kentucky and northern Tennessee, the other (more northern route) is sometimes called the "Cumberland Road" because it started in Fort Cumberland in Maryland.  Despite Kentucky Senator Henry Clay's advocacy of this route, early in the 19th century, the northern route was selected for the National Road, connecting near Washington, Pennsylvania into the Ohio Valley of northern Kentucky and Ohio.

Fox–Wisconsin Waterway: The Fox–Wisconsin Waterway is a waterway formed by the Fox and Wisconsin Rivers. First used by European settlers in 1673 during the expedition of Marquette & Joliet, it was one of the principal routes used by travelers between the Great Lakes and the Mississippi River until the completion of the Illinois and Michigan Canal in 1848 and the arrival of railroads.  The western terminus of the Fox–Wisconsin Waterway was at the Mississippi at Prairie du Chien, Wisconsin.  It continued up the Wisconsin River about 116 miles (187 km) until reaching Portage, Wisconsin.  There travelers would portage to the Upper Fox River, or eventually, use the Portage Canal.  It continued about 160 miles (257 km) down the Fox River, following it through Lake Winnebago and continuing on the Lower Fox over 170 feet (50 m) of falls to the eastern terminus of Green Bay.

Levi Jackson Wilderness Road State Park: Levi Jackson Wilderness Road State Park is a state park located just south of London, Kentucky in Laurel County.  The park encompasses 896 acre and includes a section of the Wilderness Road that early settlers used to reach Kentucky.  The park is named for Levi Jackson, an early Kentucky pioneer.  It serves as both a recreational and historic park.

Supporting paragraphs: Peter Hackett Wilderness Road
Answer: Wilderness Road