Part 1, No. 3
Thanks to some serious research—and the magic of Ancestry—I now have a full sweep of my family’s history in America. The story, of course, is in the details. I saw how one generation would set a course that the next generation followed religiously. And I discovered one generation after another that couldn’t stay put. I wondered what made one side of the family put down roots, and the other always chasing opportunity over the next hill?
If I had my choice of grandfathers, would it be the one who is smart and lucky? Or would it be the beloved one who never seemed to catch a break? For starters, I choose John Kimbrough.

A Charmed Life
We don’t know what prepared John Kimbrough for his life in America. He was somewhat educated, as were a lot of Scotsmen back then. He had to have been a man of ambition and confidence, or he wouldn’t have risked the whole venture. And Mary certainly wouldn’t have agreed to go along, three little ones in tow, unless she possessed a certainty of her own. The timing was right, so they chanced it.
In the mid-1600s, England and London Company investors established two new colonies on the Chesapeake Bay—Maryland and Virginia. The Crown considered the “wilderness” prime tobacco-producing land, never mind that Native Tribes had long occupied every corner of the region.
The London Company’s first order of business was to fill the colonies with people. The company required perspective colonists to pay their own passage, to immigrate to a specific colony, and to live there for at least seven years. In return, the head of household would receive title to 50 acres of land called a headright. Family households of at least five people were entitled to a fifty-acre headright per person. The Kimbrough family, numbering five, began life in America already owning 250 acres of land.
All business all the time
Kimbrough was involved in business from the day he arrived at Port Tobacco. His name first pops up in the record in connection with land he had purchased in Maryland in 1667. Also, he was quick to realize the advantages of serving the colonial government, first as a surveyor and later as a colonizer himself.
With the British emphasis on settlement and property rights, lands were surveyed to verify and protect ownership, a legality especially important to both plantation owners small land owners alike. With his skill as a surveyor, Kimbrough testified as an expert witness at least 25 times on behalf of Maryland’s colonial government.
His name shows up in a few legal dispute of his own. Twice, the court ordered him to pay debts to a man named William Byrd. Kimbrough paid the first debt with a dozen of his own headrights, and the second time he settled up by paying Byrd in 15 headrights.

In 1673, it was Kimbrough’s turn to sue for an unpaid debt. In court he alleged that one Pope Avery had failed to repay him a loan worth “a fair amount of tobacco” receipts. (In early colonial times, tobacco receipts were considered money, and were used to settle debts, to pay taxes, and to pay for such things as the service of a midwife or a grave digger.) Although the suit against Pope was later dismissed, the fact that Kimbrough was able to make a loan of that size shows that he was by then a “man of substance” in business.
By 1673 he must have fulfilled his residency requirement, for that year he sold his property in Maryland. Soon he and Mary would pack up to leave Port Tobacco, this time bound for Virginia where prosperity and great tragedy awaited.
Choosing Grandfathers
Fascinating!