The Cumberland Dilleys of Guernsey Co., OH and neighboring counties moved west in two waves of migrations by two different generations. Moses! John, Aaron and Ichabod, and possibly others, appeared in Guernsey and Morgan Co. OH about 1812. The first two appeared in the 1820 census for Morgan Co. with families of children. Their generation included Jesse who with 5 sons moved to the Cumberland area of the two counties in 1839. Jonathan and James appeared in the 1840 census living together along with their parents Jesse and Ann (Smallwood) Dilley in Morgan Co.. OH..

Jesse Dilley has been a key figure for following the migrations and living sites of VA Dilleys. He was born in New Jersey in 1770, married Ann during the late 1790s in Loudoun Co. VA where he also appeared in the 181d census. His son Jonathan b 1809, in his biography, stated that he was born in the Potomac area of VA, but was reared in Shenandoah Co., VA. BY 1830, Jesse's son James had moved back to Loudoun Co., had married and appeared in the census with a small family and his brother Jonathan. Ten Years later, five members of the third generation of Dilleys living in VA moved to Cumberland. Back in Virginia, Jesse appeared in the 1820 & 1830 censuses for Shenandoah Co. before moving to Cumberland with his sons in 1839.

John Dilley of Shenandoah Co. was assumed to be the parent of Jesse on the basis of living site alone. After spending about 30 years in the county, Jesse left no other records and John was gone after 1780. John bought about 400 acres of land in a valley between two branches of the Shenandoah River located across a river and a mountain to the east of Woodstock . He sold land in 1778 and 1780, but apparently did not sell all of his land.

John of Shenandoah must have been born during the 17505 as was John of Stafford Co. based on the apparent ages of their sons. Could they be the same man? The movements of Jesse and his sons between Shenandoah and Potomac areas suggest a relationship between the two clans of what I call the Cumberland and the Washington Co. OH Dilleys. The major problem with this speculation is that for one John almost too many sons appear in the two areas. Again the assumption that the two waves of Cumberland Dilleys were closely related is based on their settling in the same areas which may be fallacious. Perhaps Jesse was not a son of John of Shenandoah Co., and that he came from New Jersey as an adult to live first in the Potomac area then moved to Shenandoah Co. He left no land records, and we don't know where in the last county he lived. What happened to John Jr. the only confirmed son for John Sr. of Shenandoah Co.? Could he be John Jr. son of John Sr. in the 1810 census of Loudoun Co.? Was Frederick Dilley in the 1810 census for Shenandoah Co. a son of John Sr.? I suspect that John of Shenandoah Co. was the same man as John of old Dunmore Co., VA and also that he was the John in 1787 tax records for Augusta Co., VA which covered so much territory in that revolutionary period in Virginia (see Don Dilley’s Timeline).