The earliest Chittys were in Virginia and Maryland spreading into South Carolina. The data on some of these Chittys is scarce in places and confusing in others. It has not been possible in all cases to relate the earliest settlers to the english families.
Scenario 1
The first Chitty known to be in the North American Colonies was arguably Valentine Chitty (1638-1668) in Virginia who went to the Isle of Wight County. This county did not exist as such until 1637 when it was renamed from Warraskoyak. The Isle of Wight records have this entry
Nothing much else is known about him other than he had a son, Edward Chitty (1682-1727) who appears to have married Margery in 1682. Actually his death date could well have been August 1721 which was the date of probate.
The dearth of records could well mean that “Valentine” was an assumed name or at least not his full name. John W Chitty (1830-1805) and his wife Francis Ballenger (1756-1826) left Virgina for Barnwell South Carolina. The had a total of 15 children establishing a strong family dynasty.
Alternative Scenario
Many researchers prefer to argue that Edward Percival Chitty was the first and that he was in fact the Edward mentioned above but borne in Limpsfield, Surrey, England to John Chitty and Joane Heath. The spouses differ. There is not a lot of evidence but it seems to support either option! The disadvantage of this is that it ignores Valentine Chitty who definitely existed!
The confusion has been exacerbated because of the commonality of names.
Maryland Chittys
The first Benjamin Chitty was born in England and was married to Sarah Palmer before the year 1743. One record states he was born, lived and died in England. They had only one child, Benjamin, who was born in March, 1743 and was brought to America by his mother, who was then a widow, about the year 1748. They settled in Carroll’s Manor, Frederick County, MD. Sarah Palmer Chitty, the widow, remarried probably ca. 1749 to a man with the last name of Tiplet. They had one child, Mary Tippet, born 1750.
His son, Benjamin Chitty, was born 14 March 1743 in Frederick Town, then Prince George’s County, Maryland. He died 12 July 1822 in Lititz, Lancaster County, Pennsylvania having joined the Moravian community in Surry County, North Carolina in 1784. Descendants went to Ohio, Indiana, Illinois and other localities.
His wife as Maria Mary Padget, born in North Carolina and descended from William the 4th Earl of Paget (1572-1639) whose son went to Maryland. William was an Adventurer of the Virginia Company.
the following link is to a brief history of the Moravian Church in Pennsylvania. https://docsouth.unc.edu/csr/index.php/document/csr05-0360
First Generation
Children of Benjamin Chitty and Sarah Palmer
Benjamin Chitty (1743-?) m. Maria/Mary Padgett (1746-1788)
This family moved to South Carolina in 1772. But when they heard that Mary’s family had moved to NC, they followed them, settling in the neighborhood known as Hope. The move from SC was made in 1777. They had the following children:
Second Generation
Children of Benjamin Chitty and Mary Padgett
John Chitty (1766, MD-1825, NC) m. 1) Maria Margaretha Krause (1771-1815), 2) Mary (Taylor) Cook
Elizabeth Chitty (1768-1800) m. Rev. Nathaniel Baum (missionaries to Jamaica, West Indies)
Joseph Nelson Chitty (1770-1826, IN) m. 1) Mary Ann Cooper, d/o John Cooper and Elizabeth Padgett, 2) ? Black, 3) Rebecca Vest (?-1868, Shannon, IL)
Charles Chitty (1772-1836) m. Elizabeth Heckedorn (1775-1824), d/o John Heckedorn and Catharina Clewell of York PA
Dorcas Chitty (1775-1806) m. David Peter (moved to Ohio)
Benjamin Chitty (1776-?) m. Nancy James (a widow)
Mary Chitty (1779-1781)
Sarah Chitty (1781-1815) m. Samuel Luckenbach (1778-1846)
(Samuel Luckenbach was a blacksmith. Both are buried in the Old Moravian Cemetery in Bethlehem, PA)
Jacob Chitty (1784-?) m. Rebecca Rudy/Rude/Ruede
Mary Magdalena Chitty (1787-?)
from: http://www.fmoran.com/chitty.html
There is a useful book by Lyman Priest on the Chitty family in the USA published in 1995:
The Chitty Family, Benjamin and Sarah (Palmer) Chitty and Their Descendants, ISBN 9780608048000, 0608048003
An extract can be accessed here relating mainly to the early Chittys.