Genealogy Meets American History in this 11th Generation Family Business

We all know that the United States started out as a set of colonies in the 1600s. The colonists farmed, built towns, raised children and farm animals to create a life for themselves in this new world.

As these colonies multiplied and became a country, an early farming outpost, now called Shirley Plantation, also grew along the James River in Virginia and is still in operation today.

Found on a list of the oldest multi-generational family-owned businesses in the United States, Shirley Plantation has seen 11 generations of family pass ownership of this property.

For any family-owned business to succeed for multiple generations, let alone four centuries, is simply amazing. This family business has grown right alongside this great nation.

Origins of the Shirley Plantation

The Shirley Plantation was originally known as West and Shirley Hundred created from the 1613 Crown Grant to Sir Thomas West, the Baron De La Warr (as in Delaware, the bay and state of his name), and his wife, Lady Cessalie Sherley. Their marriage was an engagement of two families of the peerage in addition to being a marital union of individuals.  Sir Thomas was a great promoter of the Virginia colony and the largest shareholder in the Virginia Company of London, which had the royal charter 1607-1624 for the colonization and trade of Virginia. West was also the Royal Governor and Captain General and sailed to Virginia just in time to prevent the abandonment of Jamestown after the Starving Time of the winter of 1609-10. He re-invigorated the colony but suffered from the ‘seasoning’ many colonists experienced (and possibly gout) and returned to England after a few months. His three brothers all acquired land in Virginia and two of them were also Governors of the colony.

Shirley was Sir Thomas’ pick of where he wanted his plot of land in the colony as the land was fertile soil in riverfront ‘old fields’ (cleared and abandoned by the Weanack tribe) and is as far inland as possible (away from the Spanish threat) at the end of ocean-going navigation for the larger class of cargo ships. At one time, 140 ton ships could navigate to Shirley on the James River but only 100 ton ships could go further upstream through the narrower bends and over shoals towards the falls at what is today Richmond in the 16-teens).

Early on, the long title that is West and Shirley Hundred was shortened to Shirley Hundred or just Shirley. The Plantation designation came in the past half century as part of an effort by the Virginia Department of Tourism.

The term “Hundred” was an old term by the 1600s that had come to mean a venture or endeavor. In earlier times (medieval period), it meant a subdivision of an English county in which 100 men could be called upon to keep the King’s peace. By the 1600s, Hundred meant company – more in the sense of a business association than of a militaristic designation of size.

Tobacco was first raised here in the earliest of times, around 1615-16 and for the next 200 years as a commercial crop cumulating in the Golden Era of Tobacco around 1700-1750, By the time of the Revolution, tobacco cultivation suffered from chronic overproduction, poor cultivation practices (tobacco is not “bad for the soil” as has been claimed so much as poor management practices such as growing tobacco year after year without fallow periods or the colonial version of rotation of crops, which was known to reduce soil fertility), and weak market prices.

Genealogy of the Shirley Plantation

“We are otherwise indistinguishable from any other person you might meet.  Everyone has eleven generations; we just stayed in one spot.” – Charles Carter III

With 11 generations of a single family owning and operating the same business, at the same location for over four centuries, it’s a good question to ask if they know where they all came from.

The family heritage throughout the 11 generations is primarily European. Being a part of the original colonization of America, they’ve descended from England within the specific areas of London and Shropshire. Other European influence includes a mix of Danish, Scottish, Irish.  There’s even some Native American.

The Historic Christ Church Foundation in Lancaster, Virginia published the book ‘A Genealogy of the Descendants of Robert “King” Carter’ which shows 85,000 descendants over the generations.


  Edward Hill III
 Elizabeth Hill & John Carter
Charles Carter
Robert “King” Carter

Hill Carter
Robert Randolph Carter
Alice Carter Bransford & Marion Carter Oliver
Charles Hill Carter II

  1. Edward Hill I (d 1669) – Founder
  2. Edward Hill II (1636-1700) – Son
  3. Edward Hill III (d 1726) – Grandson
  4. Elizabeth Hill ca. 1700 – 1770 Great granddaughter
  5. Charles Carter (1732-1806) – Second great grandson
  6. Robert “King” Carter (1774-1805) – Third great grandson
  7. Hill Carter (1796-1875) – Fourth great grandson
  8. Robert Randolph Carter (1825-1888) – Fifth great grandson
  9. Marion Carter Oliver (1858-1952) & Alice Carter Bransford (1852-1928) – Sixth great granddaughters
  10. Charles Hill Carter, II (1919-2009)  – Seventh great grandson
  11. Charles Hill Carter III (b. 1962) and brother Robert Randolph Carter (b 1964) – Eighth great grandsons
  12. Charles Hill Carter IV and Lela Grace Carter, brother and sister, born 2016 – 9th great grandchildren
Charles Hill Carter III and Randy Carter
 Charles Hill Carter IV & Lela Grace Carter

Transferring Ownership to a New Generation

When the time comes, it’s expected that new generations will take over the Shirley Plantation. Surprisingly, this never caused any major stress in the family, or at least none that come through from the extensive family archive. Each new generation knows what is coming and that they were selected for the role from an early time.

Besides the challenges of debt, financial/market crisis, war, fire, taxes and litigation to family businesses over the centuries, the ‘internal’ risks of a weak successor, shoddy steward, divorce, or an outright “bad apple” (who prefers cash to facing challenges); the family through the generations welcomed a sense of duty and the honor of carrying on the family heritage, as well as engaged in a bit of strategic planning in choosing successors.  There’s been situations that could have gone differently of course.

The Shirley Plantation was usually passed from father to son in all but a few generational successions which still kept it in the bloodline.  Other assets and property are given to siblings but the main tract of the plantation and its heritage assets are kept whole by going to one designee.

The concern was that splitting the property would, in a few generations, relegate a grand estate to a sliver of what it was.  Same view of splitting the interest, or giving shares to split down the generations, which can cause a forced sale to settle disagreement.  The question is “Do you want a democratic split of heritage and assets or do you want to pick the best single choice (with tiers of back-ups) for the heritage to survive intact?”  If it’s only about seeking a “fair distribution amongst siblings” of money/assets, the heritage often looses and is dissipated rather than concentrated.

In 1952, Marion Carter Oliver, the last of the wife and two daughters of Robert Randolph Carter, died at 94 years.  There was no issue from the two daughters, a situation their grandfather, Hill Carter, had provided for in his will.  His will stated that the last survivor of Robert’s wife or daughters, should name an heir bearing the name Carter from his line.  That’s estate planning from the 1870s.

In 1794, Charles Carter thought little of his daughter’s husband’s business acumen and added a codicil to his will that Henry Lee should not take control of his wife’s property from Charles’ estate.  Instead, it would be held in trust for her by four of her brothers.  Henry Lee was a Revolutionary War hero and Governor of Virginia but an unfortunate manager with a trail of debt and creditors following him most of his adult life.  Estate planning from the 1790s…

However, the place has not always passed from father to son, nor to eldest son.  Daughters, nephews of the line, trustees, guardians, and stewards have all played significant roles. Edward Hill IV died in 1706 aged 16 and without issue.  His youngest sister, Elizabeth, was the only sibling still unmarried and at home.  Elizabeth knew from childhood that her father needed to pass along Shirley, had no living son to pass it to, the transfer was going to be by marriage and that her two sisters married Englishmen and moved to England.

John Carter’s (1690-1742) 1723 marriage to Elizabeth meant that Shirley was his even though it passed through her as women could not hold an estate under the law of the time.  When he died in 1742, Elizabeth had only a life estate rather than ownership, meaning she could live there but could not sell the property. She remarried in 1752 to Bowler Cocke of Bremo.  Upon their deaths in 1770, Charles Carter returned to Shirley with his family from Corotoman.

In the last generation, an L.L.C. to hold the heritage assets was formed with the two parents and the designated heir, Charles Hill Carter III, having ownership.  The parents’ portions passes to a trust and the heir is the trustee of their estate.  Also, there is now also a conservation easement on 147 acres including the historic area which means it cannot be subdivided or developed other than for limited agricultural or tourism purposes. The trusts and easements add protection and support to future generations in preserving the heritage and the family.

The Shirley Plantation Today

As tobacco has not been grown on the plantation as a commercial crop (“cash crop”) since 1817 , it has been raised periodically as a “home crop” (for home & local use).

Today, Shirley is focused upon crops for local consumption (pecans, freshwater shrimp and grapes) or what the ancestors would call “home crops” as much as their focus is upon “cash crops” of corn, cotton, wheat and soybeans to the global markets.  At the same time, Shirley is working to recover and preserve the original soil their ancestors farmed to improve agricultural productivity. The soil has been lost over time with erosion along the James river.

In 1970, through the work of Charles Carter II, the house was placed on the National Register and is recognized as a National Historic Landmark.

Completed in 1738, “Great House,” is largely in its original state and is owned, operated, and resided in by direct descendants of Edward Hill I which now includes a new set of 12th generation twins who may one day take over the plantation.

The upper floors are occupied by members of the eleventh generation of the Hill Carter family, while the bottom floor is open for tours. You can visit the Shirley Plantation which is open for touring every day from 9:30 a.m. to 4:30 p.m., and closed on Thanksgiving and Christmas Day.