The Riddle Newsletter

Genealogy is Heredity

Volume 6, Issue 1, December 1999

• Sir John Riddle
• Two Tom Dooleys
• Tory Oak Dedication
• James M. Riddle
• Descendants of Samuel Riddle
• Internet Update
• The Riddles of Pensacola

Sir John Riddle – Our Ancestor?
Richard Riddle

Recent information provided by Danny Riddle of Winston-Salem may support “speculation” that our forefather John W. Riddle, Sr. was related to the Riddells of Roxburghshire, Scotland. As I stated in my book, Some More Riddles Of North Carolina, page II-19, Samuel Riddle may have been the father of John Riddle. Danny discovered a paper titled Riddle Family written by Dr. Walter Wayne Smith, of Moscow, Idaho, dated December 15, 1950. 

In Dr. Smith's paper he asserts, “The Riddles of New Jersey, Maryland, Virginia, North Carolina are descended from the Riddells or Riddles, of Roxburghshire, Scotland.” He then gives the lineage of Sir John Riddell, the 1st Baronet of the Riddell of Roxburghshire back to Galfridus Ridel who was a knight in the service of William The Conqueror. Charles I, King of England and Scotland, conferred Sir John's title of baronet on May 14, 1628.

Additional information about the Riddells of Roxburghshire can be found in
Some More Riddles Of North Carolina beginning on page I-16. Dr. Smith states that Samuel Riddle was the father of George and Randolph. We know that Randolph is the brother of our John. We also believe that Tyre Riddle was also a brother of Randolph and John. Dr. Smith demonstrates the lineage from Sir John Riddle, 1st Baronet, Riddells of Roxburghshire down to our John W. Riddle, Sr. as follows:  

1. Sir John Riddell (1st Baronet) 
2. Sir William Riddell (2nd son of John. His older brother Walter became the 2nd Baronet) was knighted at an early age and became the Governor of Desborough, Holland and had sons Walter and William. 
3. William Riddell born about 1663 came to New Jersey with his brother Walter and took service under the Proprietors and became a member of the Council of West Jersey. He acquired land interests in Maryland and his known sons were James, Walter, and William.
4. Walter Riddle born about 1696 is believed to have moved from New Jersey to Maryland and then to Virginia. He had sons Basil, Julius, and Zachariah. 
5. Basil Riddle, born about 1720 moved to Accomac County, Virginia and had a son Samuel. 
6. Samuel Riddle, born about 1740 moved from the eastern shore of Virginia to North Carolina. He had sons George, Randolph, John and Tyre. 
7. John W. Riddle, Sr. our forefather who was the first Riddle to settle in what was Buncombe County (now Yancey County) before 1805. Over 4,000 descendants and allied families of John have been documented. If Dr. Smith is right, John was a seventh generation descendant of Sir John Riddell, 1st Baronet of Riddells of Roxburghshire.

G. T. Ridlon, in his book
History of the Ancient Ryedales and Their Descendants in Normandy, Great Britain, Ireland, and America on page 350, supports Dr. Smith's claim that Samuel Riddle was the father of George and Randolph. If he was the father of Randolph then he had to be the father of our John.

On Friday, March 19, 1999 Danny Riddle received a message from Sue Riddle Emerson niece of Elsie Riddle wife of Dr. Smith. I have abstracted the message as follows: My Aunt Elsie Riddle and her husband Walter Wayne Smith, Ph.D., did a lot of research in the late 40's and early 50's. Wayne died in 1961 and Elsie in 1971. 

Elsie sent all of their data to the Rowan County Library in (Salisbury) North Carolina. Last year my husband and I became interested in genealogy and hired a genealogist in North Carolina to copy all of their papers. After looking at all of these pages how Uncle Smith made the leap back to Zachariah, being the son of Walter) and further, is beyond me. The search for the lineage of our John Riddle does not end here. I feel that John is connected to the Riddells of Scotland and Ireland but presently I am unable offer any proof. In the meantime, I as well as the many other Riddle researchers will continue our quest.

Two Tom Dooley’s
Richard Riddle

In the Riddle Newsletter, Volume 5, Issue 2, June 1999, Samuel Riddle Civil War Record, page 2, column 2, I falsely stated that Major Dula (Thomas J. Dula) was the subject of the song Hang Down Your Head Tom Dooley. For the record, this Thomas J. Dula was not the subject of that song and had nothing to do with the death of Laura Foster. 

This Thomas Dula was born in Caldwell County, North Carolina and became a lawyer in Lenoir, Caldwell County, North Carolina. When the Civil war began he entered the Confederate army as a Private in Company I, 26th North Carolina Regiment. He was then returned home to form a new company, which he accomplished. This company became Company H of the 58th Regiment North Carolina Infantry with Thomas Dula as Captain. He was later promoted to Major and then to Lieutenant Colonel and served as commander of the 58th numerous times. 

In 1871 he moved to Wilkesboro, Wilkes County and the next year he was elected to the State Legislature. In 1900 he was elected to the State Senate. Now the other Thomas Dula. If you are wondering how this story relates to the Riddles, it doesn’t but it’s a good tale. I’m sure that our readers will remember the song, Tom Doole. There have been several versions recorded with the first by G.B. Grayson of Laurel Bloomery, Tennessee and Henry Whittier for Victor Records on October 1, 1929. 

G.B. Grayson is the nephew of the Grayson mentioned in the ballad. 

Grayson/Whittier version of the ballad Tom Dooley.  

Hang your head Tom Dooley 

Hang your head and cry
You killed poor Lorrie Foster 
And you know you're bound to die  

This world and one more than

Where do you reckon I'd be
If it hadn't been for Grayson 
I'd a been in Tennessee

Hang your head Tom Dooley
Hang your head and cry
You killed poor Lorrie Foster
And you know you're bound to die
The Kingston Trio recorded a more popular version in 1959. A movie was also made in 1959 and called
The Legend of Tom Dooley, with Michael Landon (pre-Bonanza days) as the Confederate soldier who, unaware that the war is over, robs a Union stagecoach and is branded an outlaw and murderer. 

The movie was based on the song made famous by the Kingston Trio but is all mostly fiction and bares little resemblance to the true story of Tom Dula (Tom Dooley). 

The Kingston Trio's version.   


Hang down your head Tom Dooley 
Hang down your head and cry
Hang down your head Tom Dooley
Poor boy you're bound to die

I met her on the mountain

There I took her life
I met her on the mountain
Stabbed her with a knife


This time tomorrow
Reckon where I'll be
If it hadn't of been for Grayson
I'd have been in Tennessee


This time tomorrow
Reckon where I'll be
Down in some lonesome canyon
Hanging from a wide oak tree

The real story of Tom Dula (Dooley) follows. The second Tom Dula also that also served in the Confederate army but was from Wilkes County, North Carolina. He was known to have led an active lifestyle with the women of his immediate neighborhood. 

The Laura Foster mentioned in the song, her cousin Ann Foster Melton, who was married to James Melton and a Pauline Foster were all lovers of Tom Dula. As revealed in the court records, early one morning in 1866, Laura Foster took her best clothes and her father's horse and left for her rendezvous with Dula who had supposedly gone to meet the justice of the peace so they could be married. 

Laura disappeared and Tom Dula fled Wilkes County. After a prolonged search, Laura’s body was found and warrants were issued for Dula’s arrest. A young stranger appeared at Major James W.M. Grayson's farm at Trade, Tennessee and asked for employment as a farm worker. He said his name was Tom Hall and that his shoes were worn out and he needed money to pay a local shoemaker for a pair of boots. 

He also claimed that he came from Wilkes County by way of Watauga County, North Carolina. He toiled for four days and left early the fifth morning on foot wearing his new boots. Late that afternoon two deputies from Wilkes County, North Carolina appeared at Major Grayson's farm. They informed the Major that Tom Hall was actually Thomas Dula, a fugitive wanted for a shameful murder on the east side of the Blue Ridge. 

Major Grayson invited them to spend the night and next morning, July 11, 1866 agreed to help find Dula. He buckled on the seven shot rim fire Deemore .32 caliber revolver he had carried throughout the Civil War and led the deputies in the direction Dula had fled. They overtook the former Confederate at Pandora, nine miles west of Mountain City, soaking his feet in Doe Creek and seeking relief from the blisters the new boots had created. 

Grayson dismounted and told Dula he was under arrest. He put Dula behind him on his horse and returned to his home near Trade where they spent the night. The next morning Grayson again tied Dula’s hands behind him and his feet beneath the belly of the horse and headed for Wilkes County to deliver the prisoner to jail. Major James W.M. Grayson of the Union Army is the “Grayson” mentioned in the Tom Dooley ballad. 

Tom Dula and Ann Foster Melton were charged with murder. In the coming trial Zebulon Vance, ex-Governor of North Carolina and Civil War hero, volunteered to represent Dula whom he may have known during the war. According to the court records Ann Melton had been having an affair with Tom Dula for many years. James Melton, Ann’s husband was a cobbler and kept Tom Dula and the community in shoes. 

The court records describe him as a good and Godly man. James and Ann lived in a big one-room house with three beds. Tom and Ann would sleep in one while James Melton, her husband slept alone in another. After a much-publicized trial and an appeal Dula was found guilty. He was sentenced to death and hanged in Statesville, North Carolina on May 1, 1868. 

Ann spent two years in prison and later died of the “pock” (syphilis). According to court records both Ann and Laura had syphilis. The exact motive for the tragedy may never be known, but a web of romantic intrigue, jealousy, and spite emerged between Dula, Ann Melton, and Laura Foster. Today, some believe that Ann Melton did the actual killing. The grave of Tom Dula and Laura Foster and the jail cell where Dula spent many months, may be currently found in Wilkes County, North Carolina.

Tory Oak Dedication
Richard Riddle

On Sunday, September 26, 1999 hundreds of people gathered in “Old Wilkesboro” to witness the dedication of the Tory Oak Site and to take part in several events that celebrated the history of Wilkesboro. The celebration began at 2:00 PM and continued until well after dark. String, as well as drum and fife bands provided live music.
Some of the events included persons dressed in costumes that reflected the Revolutionary and Civil War period plus the firing of cannons and flintlock rifles. There was a blacksmith and an herb lady in attendance and a tour of the Old Wilkes Jail were Tom Dooley (Dula) had been confined while awaiting his murder trial. About 3:00 PM the dedication of the Tory Oak Site commenced. 

The Tory Oak Site is a red brick structure approximately two and a half foot high and ten to twelve feet in diameter constructed over the location of the Tory Oak. The top is inlayed with red bricks inscribed with a name on each. Prior to the final construction of the top people were allowed to purchase a brick and have a name inscribed. On the right top of the structure one of the inscribed bricks contains the name “Capt. William Riddle.” This brick was laid in honor of a man who died fighting for beliefs that he held dear. 

The four people standing on the right side of the above photograph are Ron Blevins, a descendant of Capt. Riddle, Richard Riddle, Jack Goins, another descendant and Jan Baity, the Executive Director of Old Wilkes, Inc. holding the plaque. 

This is the Tory Oak prior to its destruction. A storm on June 12, 1989 left only a six-foot stump. In the June 1997 Riddle Newsletter an article titled The Tory Oak Is Gone was published which explains the history of the 300-year-old Tory Oak and its demise. The Tory Oak is, according to some accounts, the tree from which Captain William Riddle and one or more of his sons were hanged, thus the significance to the Riddle family. 

Over the past few years the
Riddle Newsletter has published several articles dealing with Captain William Riddle and his descendants. For those interested in more information about Captain Riddle see these past issues of the Riddle Newsletter. Captain Riddle Hanged in Wilkesboro, NC, June 1996 and William Thomas Riddle Tory of Patriot? December 1996 by Richard Riddle and William Riddle 1740-1781and Riddle Research Trip to Tennessee, North Carolina, and Virginia, by Mary Hill in the December 1997 issue.

James M. "Mack" Riddle (1913-1999)

It is with deep regret and sadness that we make the following announcement received on October 30, 1999 from cousin Patricia Y. Stallard. It is with great sorrow that I report to all interested Riddle cousins that Mack Riddle died on October 28, 1999 in Holston Valley Hospital in Kingsport. All his friend and relatives including many Riddle cousins will miss him. He was well known throughout the Tri-Cities area as Mr. Fourth of July and as the backbone of the annual Riddle Reunion held in August in Kingsport. He was my father's favorite cousin, being more like a brother to him. 

I was in the hospital with my Mother who is also a Riddle and Mack's distant cousin and we watched along with his faithful wife Mamie as he valiantly struggled to live. From close observation I can testify that the Riddle heart is strong to the end and continues to be considerate of others to its last beat. Subscribers to the
Riddle Newsletter will remember that I attended the Riddle Reunion in Kingsport, Tennessee on August 21, 1994 and again on August 20, 1995. 

Mack had been the spark plug of this Riddle Reunion for many years and was interested in his Riddle heritage. He is a descendant of Tyre Riddle brother of John W. Riddle, Sr. (1764-1844). Mack served five years in the U.S. Army during World War II and was retired from Eastman Kodak after 40 years of employment. Mack was truly a caring person and enjoyed making people feel good. He was a partner to Frank Taylor in a well-known comedy and variety act known as the “Frank and Mack Show.” Those who knew him will feel a void that his passing will leave but we can take comfort in knowing that he has gone to a far better place. I have taken the liberty of reprinting my article about my last trip to this Riddle Reunion. This appeared in the December 1995
Riddle Newsletter.


On August 20, the descendants of Tyre Riddle gathered for their reunion in Kingsport, Tenn. Tyre was a brother to our John Riddle. John named his son Benjamin Tyre in honor of his brother Tyre. By the time I arrived, Ed and Dot Riddle from Houston were already there. About an hour later Elizabeth Riddle Reynolds and her daughter from Italy, Tex., showed up and had Liz’s brother Bill, his wife, and their son with them. 

Bill and his family live in Bridgeport, Ala. So there we were – descendants of three Riddle brothers Tyre, Randolph, and John, all joining hands and praying together again. I don’t know if this set of circumstances will ever happen again but I can’t help hoping that they will. Yes, thank God, I was able to attend all three Riddle reunions. If you would be interested in attending one or more, I’ll find out the exact date, location, and time they are to be held and publish that information in the next newsletter. In the meantime, the Texas reunion is held every year on the Fourth of July unless that date falls on a Sunday. Next year the Fourth of July, 1996 will fall on a Thursday. The North Carolina and Tennessee reunions are usually held in mid-August. The North Carolina reunion is held on a Saturday and the Tennessee reunion is held on a Sunday.

Descendants of Samuel Riddle
Richard Riddle

Helen Catherine “Holly” Riddle, daughter of Dr. J. Iverson Riddle and great-great granddaughter of Samuel Riddle contacted me in August of this year. She is the Executive Director of the North Carolina Council on Developmental Disabilities. By training Holy is an attorney (Georgetown University Law Center, '87) and Master's-level special educator. 

She is married to Dick Adrianus Harmsen who is an administrator at Orange-Person-Chatham Mental Health Program. Dick is a native of the Netherlands and has been a resident of the U.S. for about ten years. Holly and Dick have a nine-year-old son Soren Adrianus Harmsen. Holly and family live in Chapel Hill, North Carolina. A warm welcome to our new Riddle cousins.

Internet Update
Jim Hartung

I would like to update everyone about the Stokes Co., NC Riddle web site. I have moved the site to a new ISP (Internet Service Provider) in order to increase the space available for information plus improved performance. The new WWW address is On the main page choose Riddle Family from the menu bar and you will be taken to our Riddle family web site. 

A new feature of the Riddle web site is a section for early photos of our Riddle ancestors in the
Database section. If you have an old photo of your Riddle ancestor and would like to see it displayed on our web site please send a copy to either Richard Riddle or myself. A scanned image via e-mail or a hard copy sent via the postal service will be happily accepted.  

Richard Riddle

2725 London Lane
Winston-Salem, NC 27103-5726
E-mail Richard Riddle

Jim Hartung

601 Rowe Drive Aberdeen, MD 21001-1614
E-mail Jim Hartung

The Riddles and Pensacola, North Carolina
Richard Riddle

Pensacola, North Carolina is the ancestral home of many Riddles from Yancey County and many descendants still call it home. Although the Riddles were not the first white people to settle the Pensacola community they were among the earliest. It is believed that the Allen, McMahan, Ray, and Wilson families settled near the confluence of Cattale Creek, Laurel Branch, and the Caney (Cain) River in the late 1780s. 

John W. Riddle, Sr., the first Riddle to settle in Buncombe, now Yancey County bought land on the Caney River from George Wilson in 1805. Many of John’s sons and daughters intermarried with the children of these early settlers and built their homes and raised families in the Pensacola area. When and how did this area, which is on the highest mountain east of the Mississippi, get its name? 

The following article attempts to answer these two questions. My theory is that someone in the area bestowed the name in remembrance of Pensacola, Florida. What was the significance of the Pensacola name and why would anyone want to name an area in the mountains of North Carolina after a seaside town? Did early settlers arrive from Pensacola, Florida? None that are known. Most early settlers immigrated from Virginia, other sections of North Carolina, and a few from South Carolina and Tennessee.

Was the Connection Established During the American Revolution?

In 1763, the British gained control of Pensacola along with the rest of Florida through a treaty with Spain in exchange for Havana, Cuba. Britain had captured Havana during the Seven-Year War, 1756 to 1763. The British divided Florida in two parts, West Florida with Pensacola as the capital, and East Florida with St. Augustine as it’s capital. Both Florida’s remained loyal to Great Britain throughout the War for American Independence, 1776 to 1783. However, Spain, participating indirectly in the war as an ally of France, captured Pensacola from the British in 1781. 

In 1784, Spain regained control of the rest of Florida as part of the treaty that ended the American Revolution. Although some of the early Yancey County North Carolina settlers served in the American Revolution, as far as can be determined, none had connections with Pensacola, Florida. Also no important battles were fought in the Pensacola area during the Revolution.

Was the Name Related to the Civil War?

I have been unable to locate any land records that made reference to Pensacola prior to 1850 and the first appearance of Pensacola in the Yancey County census was 1870. From 1840 through 1860, residences of this sector of the Cain River Valley had been included in the Burnsville Township, Yancey County census. I also knew that the first Pensacola Post Office was established in May 1875 with Samuel Riddle as the first Postmaster. 

I was even more convinced that Pensacola received its name after 1860 when I discovered that Pensacola became a township on December 7, 1868. The
Yancey County Court of Common Pleas and Quarter Sessions, Court Minutes, Sept. 1860 - June 1869, (pages 140 -150, cover Oct. 26, 1868 to June 22, 1869) contained a description of the boundaries of the ten townships that comprise Yancey County. The ten townships named were: 1st District Burnsville, 2nd District Caney River, 3rd District Egypt, 4th District Ramseytown, 5th District Hollow Poplar, 6th District Jacks Creek, 7th District Brush Creek, 8th District Crabtree, 9th District South Toe River, and 10th District Pensacola. 

If Pensacola became a township in 1868, three years after the Civil War, I hypothesized that several of our returning veterans might have begun referring to this area as Pensacola as a result of a connection they had with Pensacola, Florida. While researching the Civil War, I had determined that several men from the Cane River Valley had fought alongside troops from Florida. Maybe these veterans had become friends with troops from Pensacola, Florida and they named this area Pensacola in their honor?

When Did Pensacola Become A Voting Precinct?

While reading the News From Yancey - Articles From Area Newspapers - 1840-1900, collected with Commentary by Lloyd Bailey, Sr., I discovered an article that contained the results for the Yancey County state election held in 1854. The Asheville News, August 10, 1854, published the article. It described the election precincts as Burnsville, Cane River, Egypt, Jack’s Creek, Cane Creek, Snow Creek, Grassy Creek, Oake’s, South Toe, and Pensacola. If Pensacola was a voting or election precinct by 1854, it certainly did not obtain its name because of a connection to the Civil War. Obviously this needed more research.

When Did Pensacola Become A Public School District?

In the book, Images of Yancey, published by the Yancey History Association in 1993 on page 62, the following is found: “with the first meeting of the county’s (Yancey) Superintendents of Public Instruction in 1842. Thirty-three local districts were formed and a Committeeman elected from each. Among the districts were: Jacks Creek, Pig Pen, Burnsville, Young’s, South Toe, Pensacola, Hinton Creek, Bald Mountain, Egypt, Daniel Carter’s, Paint Fork, Walnut Creek, Shelton Laurel, Big Rock Creek, Old Fields of Toe, and Grassy Creek.” If Pensacola was established as a public school district in 1842, that part of the Cane River Valley was named Pensacola prior to 1842.

First Reference To Pensacola In Yancey County Court Minutes

On July 29, 1998, I made my first trip to the North Carolina State Archives to research the Pensacola name. My first task was to search the minutes of the first Yancey County Court held in the spring of 1834. Not only did I find the 1834 Court minutes but all Court minutes through 1844 written in old longhand script. In February 1835, Constables were elected (appointed) to the Rock Creek Company, Jack’s Creek Company, Crabtree Company, Grassy Creek Company, Ivy Company, and Cain Creek Company. No mention of Pensacola. In June, 1835, Justices were appointed to take a list of taxable property for the year 1836 for the following Companies: Capt. Wisemons, Grassy Creek, Cain Creek, Rock Creek, Jack’s Creek, Snow Creek, Crabtree, Paint Fork of Ivy, Capt. Woodards, Bull Creek, and Laurel and still no mention of Pensacola. In the minutes of the October 9th 1837, I found: “Ordered by the Court that Samuel Austin oversee by a survey of view from William Wilson’s Mill in Pensacola by the way of Bolins Creek to Burnsville and that all hands that formally kept up the road leading into said settlement work said road.”

So it appears the name Pensacola was being used to describe part of the upper Cane River Valley as early as 1837.

Was Pensacola Connected With the War of 1812?

I questioned Bill Hensley about the early settlers and Pensacola. Bill was born in Pensacola in 1925. He though only six or eight families lived in the area before 1820 and that the name Pensacola arrived from the Gulf along with the local militia returning after war of 1812.

Judge Robert Orr and I have been exchanging e-mail messages about this question. In a message from him on July 17, 1998, he had thought of two more possibilities. First, since Burnsville was named for Otway Burns, a naval hero of the War of 1812, Burns may have had contact with Pensacola, Florida and that may have influenced the naming of Pensacola. Unfortunately Judge Orr could find no connection between Otway Burns and Pensacola, Florida. The second possibility was that prior to the Battle of New Orleans, General Andrew Jackson and his troops captured Pensacola from the Spanish because the British used it as a supply base. 

That comment by Judge Orr caused me to recall Bill Hensley’s comment. I asked Bill for the names of the returned veterans. Bill replied that James McMahan and Jacob Silver had been in the Buncombe County, Third Regiment, North Carolina Militia. In the book Muster Rolls of the Soldiers Of The War Of 1812: Detached From The Militia Of North Carolina, In 1812 and 1814 I located the names of Jacob Silver and James McMahan just as Bill claimed.

War Of 1812 - Battle of Pensacola

In late October Andrew Jackson marched on Pensacola, Florida then still under the control of Spain. Arriving on November 6, 1814 with four thousand men he discovered seven British vessels with over one hundred guns guarding the western approach to the city. He conveyed a message to the Spanish Governor, Don Matteo Gonzales Manrique demanding the surrender of Forts Barrancas, St. Rose, and St. Michael “until Spain can preserve unimpaired her neutral character.” 

Not receiving a satisfactory reply, on November 7th he sent a force of 500 men to feint an attack from the west while his main body of troops bypassed the city through the woods and attacked from the east. Governor Manrique soon surrendered Pensacola after heavy fighting in the outskirts of the city. As Jackson prepared to attack Fort Barrancas the British blew up the fort and withdrew to the east. He then completed the neutralization of Pensacola by blowing up Fort St. Michael.

Students of the history will remember Jackson and the “Battle of New Orleans”, but few remember the “Battle of Pensacola.” Although Jackson was criticized for his invasion of Spanish territory, his action at Pensacola prevented the British from using it as a base for attacking New Orleans. The victory at Pensacola amplified the confidence of the America troops and bestowed new faith in their leader. Perhaps this is why the returning veterans of the Cane River Valley in the Black Mountains of North Carolina decided to call their little community “Pensacola?”