Sometimes I wonder why it has been relatively easy for me to have my ancestors jump the pond back to their European origins, but it has been so difficult to do with most of my husband’s lines. I can barely find their origins on the East Coast, never mind across the ocean. Then I stop and think for a moment and remember that most of his lines go back to Virginia and the Carolinas.
So it goes with his Riddle family. I wrote about Mary Riddle who married Henry Nations yesterday. However, Mary was only a stepmother to Dave’s great great grandfather, Joseph Michael Nation/s. Joseph Michael, also called Mike, married Christianna (aka Annie) Riddle, who was the younger sister of his stepmother, Mary Riddle. (Hmmm, Mary was the stepmother of her own sister. Interesting!)
Mary and Annie Riddle were the first and sixth born children of ten born to Isaac Riddle and his wife, Catherine Johnson. Isaac married Catherine on 26 August 1824 in Wayne County, Kentucky. They have hundreds of descendants and a lot is known about the family from their time forward.
I shared this photo in the Nations post, but only identified Mary Riddle Nations. Here are all the surviving siblings probably in the 1890’s:

Front: Betty, Mary, Joseph
Back: Catherine (Happy), Annie, Rhoda, Philip
There are a several hindrances to documenting the Riddles further back than Isaac’s parents, Joseph Riddle and Rhode Monk. First is the fact that there were so many darn Riddles, it is hard to separate them all out, especially when it is one of those families that repeated the same names in every family of each generation. Second, they never let any grass grow under their feet. All branches of the family kept on the move. Lastly, family lore kept descendants from finding out the real story for many years! The story has been retold many times about the heroic Captain William Riddle, a soldier of the Revolutionary War.
Because vital records are sorely missing in this time period, it’s necessary to look at both Joseph Riddle and his wife, Rhoda Monk, to even begin to sort out the truth about this family. Land deeds and court records allow the story to be pieced together.
First is the family of Joseph Riddle. Joseph was born about 1777 probably in Virginia, but possibly in North Carolina, as the family lived near the border between the two states. There is actually a death certificate filed for him in Cumberland County, Kentucky.
Joseph’s parents, William Riddle and Happy Rogers, are likely correct. Part of the family lore was that Hopy was an Indian, claimed I guess because of the name “Hopy.” However, her given name was likely Catherine as descendants named that were often called “Happy” in many records. “Hopy” may just be a misspelling of “Happy.”
Happy may or may not have been the daughter of Doswell Rogers.
Joseph’s death record correlates with a birth year of 1779. The 1850 census gives his age as 73, thus born about 1777 and he gives his place of birth as North Carolina. Family lore (no proof yet found) says that Joseph was a twin brother to Isaac Riddle, whose gravestone in Morris County, Texas gives a birth date of 4 April 1777 and death date of 30 November 1861. Isaac reported in the 1850 and 1860 census that he was born in Virginia.
William and Happy Rogers Riddle had six alleged children:
1. John, born about 1775
2. James, probably born about 1777
3. Joseph, likely born 1777-1779, given ages in 1850 & at death
4. Isaac, born 4 April 1777, per gravestone
5. Happy, born about 1782
6. William, born 1780-1783
Now, to continue the story, we need to switch to Joseph’s wife, Rhoda Monk. Rhoda was born about 1784 in Virginia, possibly in Russell County. Her parents were Shadrach Monk and Mary Roberts, daughter of Cornelius (Neal) and Mary Roberts. She was alive for the 1850 census, but her death record hasn’t been found and she hasn’t been located in the 1860 census. Cumberland County, Kentucky has extant death records for 1852-1859 and she isn’t in the 1860 mortality schedule. Joseph Riddle was listed as “single” in the death record, but everyone on that page was listed as single even though there are adults included on the page. If he was truly single, then Rhoda either died about 1851 or else her death wasn’t recorded for whatever reason.
There is no one document that explains the story of William Riddle and Happy Rogers, but keep in mind the FAN (Family and Neighbors) Club (all the highlighted names in this post) as you read the following excerpts from court records:
Montgomery County, Virginia
1779 Order Book 3, page 64. “First taken into consideration the unhappy situation of many individuals in this County of the New River, betwixt the River and the Flower Gap and also on the Reed Islands and Grassy Creek and Wallens? Creek, who from their remote and scattered situation have not had the opportunity of full and ample information, respecting the present Independence of America and having been deluded into acts inimical to their country by members of artful villains and emisarys sent from our enemies for that purpose and where as this court are informed from different Quarters , that those deluded people are sorry for their past crimes and desirous of being restored to the arms and friendship of the good citizens of this state. Therefore this Court ever desirous to extend mercy and to avoid prosecution as far as the safety of the State will admit, do hereby unanimously invite all persons in the above mentioned part of the county, Except as hereafter exempted.. to attend at the next court to be held in October and there throw themselves on the mercy of the Court, who hereby pledges their honor that every possible and reasonable lenity will be extended toward all such as accept hereof and give security for their future good behavior. The persons who we believe are not entitled to this invitation are Wm. Riddle & Nathaniel Britin”
Order Book 2, page 302, Nov 8 th, 1780 “ordered that Wm. Roberts, Neal Roberts, Moses Johnson, Richard Green, Richard Wright, Clem Lee and George Herd be restored their property again. It being lately taken from them by the militia of Montgomery and Washington Counties, as nothing appears against them with regard of their being enemies of the State.
Order Book 2, Page 309, March 5, 1782 “Ordered that John Roberts who has been inimical to the American cause be recieved as a citizen of this state and under the protection of the same on his taking the Oath of Alligiance and giving security for his good behavior for twelve months and one day where upon the said John Roberts acknoledges himself indebted to this commonwealth in the sum of twenty pounds
in security and Dozawell Rogers and John Rice in the sum of ten pounds each to be levied of their respective lands & Chattels and to the Commonwealth be rendered, yet upon condition that the said John Roberts shall be of good behavior for twelve months and one day from this time ordered.”
Montgomery County Court records: April 3, 1782 “Ordered Captain Wm Love return Hoppe Riddle a cow he took from her in the year 1780 or the sum of five pounds in specie.”
Then there is the story about Tory Oak in Wilkes County, North Carolina, found in Wikipedia:
At the beginning of the American Revolution, (Benjamin) Cleveland was commissioned a colonel in the North Carolina militia. He was elected to the North Carolina House of Commons in 1778 and to the North Carolina Senate in 1779. Until Lord Cornwallis invaded in 1780, the fighting in North Carolina consisted of guerilla warfare between patriots and Tories. Cleveland became known as the “Terror of the Tories” for his treatment of Loyalists. In 1779, two Tories looted the home of George Wilfong, a patriot and friend of Cleveland. The Tories used Wilfong’s clothes line to chase away his horses. The marauders were captured by Cleveland’s men, who had them hanged using the clothes line they had stolen. In revenge, a group of Tories led by Captain William Riddle kidnapped Cleveland. Cleveland’s men rescued him and he captured Riddle and two others. All three were hanged from the same tree, which became known as the “Tory Oak” and was an historic landmark behind the old Wilkes County courthouse (now the Wilkes Historical Museum).
Next, again in the Montgomery County Court Records:
Order book 2, Page 335, April 8th, 1782 John Riddle, an orphan of William Riddle of 7 yrs old to age of 21 (bound) to James Newell and James Riddle orphan of WM. Riddle , (bound) to James McCorkle and both were ordered by the court to “teach them reading, writing & Sypher and pay them the sum of 20 lbs. when they are 21.”
The final entry found in Montgomery County Court Records:
May 27, 1784 Order Bk. B- Page 63
An inventory and appraisement of the estate of Wm Riddle deceased, taken
April 24th 1784
4 ewes & three lambs——————————————–2–?
1 old mare —————————————————————–2
one small Improvement & Entry of land ————————15
1 ox4/two horses
5/————————————————————–9
1 grindstone 10/small feather bed ———————————–4-x0
1 old side saddle 20/one pair of sheep shears 2/6- –1–2.6 25–11–6
The above inventory was returned to Court and ordered to be recorded.
Test:
James McCorkle
Putting all these pieces together paints only one picture. William Riddle definitely was a soldier of the Revolutionary War, but he wasn’t a patriot, he was a Loyalist and appears to be the Captain William Riddle who was hung by Benjamin Cleveland and his men in Wilkes County, North Carolina before 8 April 1782, when his two sons, John and James, were bound out.
William Riddle’s parents haven’t yet been proven, but Isaac is a name that runs through his descendants and there is an Isaac Riddle mentioned in Fincastle County, Virginia in the 1770’s. Perhaps future research will take this line back to where it will jump the pond!