[Many thanks to Peter Kramer for lending his collection of material about the Terry family, and both him and Terry Mangum for answering my copious questions.]
James T. Terry was born in 1801, the son of James Terry, Sr. (II), and Sarah Thorpe. In 1848 James T. Terry acquired 260.5 acres on Little River adjoining the land of William Cain, the Dunagan Old Tract of land, and others, for the sum of $206.33. (Orange County Deed Book 33, Page 209.)
James T. Terry married Susanna Slaughter in 1830, and they had eleven children: Stephen O. Terry, James Francis Marion Terry, William Samuel Terry, John Scott Terry, Samuel Pegram Terry, Roland Pumphrey Terry, Sophie Terry, Sarah Ann Terry, Mary Magdalene Terry, Susanna Elizabeth Terry, and Martha Terry.
Six sons of James Terry gained some newsworthy distinction for their service in, survival of, and longevity after the Civil War. They were featured in a Morning Herald column in 1919, which was recounted by Wyatt Dixon in 1965.
Six Orange County brothers in one family served the Confederacy as soldiers and each of them returned home at the Civil War's end to resume their lives as civilians. The Durham Herald under date of Feb. 24. 1919 carried a story from an Orange County correspondent about the unusual record of the sons of James T. Terry. “Great family of brothers" was the heading given the story. Sub-heads pointed out that six of the men "are now in Orange," and the oldest of the six was 77 years of age while […] the youngest was 66 years.
The newspaper article stressed the fact that all of the men were in good health "there being but 13 years between the ages of the oldest and the youngest. Six sons from one family without a death on the battlefield or one to follow in 45 years is a record extra· ordinary."
Durham County sent many of its sons off to war in the Civil War but so far as is presently known the record of the Terry brothers of Orange County wasn't duplicated. Because of the centennial observance of that war, which will come to a climax at the Bennett Place in 1965, the recounting of the story should be of interest.
"An Orange County correspondent sends the Herald an account of an Orange family of six brothers, all of whom served in the army and all at present living," the story says in its beginning. "'They are the sons of the late James T. Terry and it is to be doubted if there is a state in the union that can claim a greater curiosity in the shape of a once belligerent family. Their records are remarkable.”
"S[tephen] O. Terry Is the oldest of the boys, being 77, and he served in Company R of the Second Regiment of North Carolina Cavalry. He was twice a prisoner of war but not wounded. "
“J[ames] F. M.Terry, aged 75, Orange County, served through the war in the same regiment as his brother, was not captured and did not feel the xxx of flying lead.”
"W[illiam] S. Terry is 72. He served the Confederacy in the 56th Regjment of Infantry, was wounded in the leg, the large shin bone being cut in two. He fell into the hands of the enemy, as had. his older brother.”
"J[ohn] S. Terry, age, 68, went into the company of his two older brothers, Company R, Second Regiment, receiving no injury and dodged the Yankees to the end. “
"S[amuel] P. Perry, age 66, went through the army, fighting in Company R, Second Regiment, . in which there were four of the boys, including himself. He was in the cavalry and received a bullet through his left lung, falling into the hands of the unspeakable Yank. “
"R[oland] P. Terry, age 64, was too young for constant service, but he guarded prisoners at the famous Confederate prison in Salisbury and at the close of the war was captured by the enemy. He was marched to Albany, New York, and put into the federal prison for a short time. Until the present week, all of these Terry brothers are in good health, there being but 13 years difference between the ages of the oldest and the youngest. Six sons from one family without a death on the battlefield or one to follow In 45 years Is a record that is extraordinary.
"The Durham people are to invite the veterans of the state here August of this year. If they come, good care of this Terry family ought to be enjoined. Everybody would like to see them live to be 100 years each and then feel like fighting the battles over again." These veterans have passed on. During their lifetime they were leaders in their community and five of them raised families. Twelve of their grandchildren donned the uniform of their country during World War II. The clipping concerning the Terry brothers was loaned for use by Mrs. L. L. Terry of Bahama.
Several of the Terry family settled on parts of the 260 acres of their father; William S. Terry built a house on the east side of Milton Road (Guess Road) across the road from the house of James T. Terry.
William S. Terry House
WS Terry ran a general store adjacent to his house (on the east side of Milton Road / Guess Road.) Two of his sons, John Wilkins Terry and Joseph Davis Terry, built houses around the intersection of South Lowell Road and Milton / Guess Road. John Terry's house was located on the west side of Milton Road, across from his father's house
John Wilkins Terry And Kate Poole Terry House
Both John and Joseph helped their father William run the general store. Joseph Terry's house was located to the north - at the northeast corner of South Lowell Road and Milton / Guess Road.
Joseph Davis Terry And Sudie Poole Terry House
The Terry land around South Lowell Road was divided among multiple heirs.
Will(iam) Terry (Jr.) lived to the south; there is a "Terry house" - as it's known colloquially - and by SHPO, that may have stood on his land, but appears to have been located to the south of his holdings noted above.
6908 Guess Road
This house is oriented away from the current course of Guess Road - a perusal of old maps and aerials shows just how much the course of the roadway has been changed (mostly straightened) over the course of ~100+ years. It's clear that the path of Guess Road used to lay to the east of this house, although it now lies to the west. It was later part of the Warren and Turnage farm.
Across the former path of Milton Road / Guess Road from this house (to the east) was the Milton Hill School.
Milton Hill School
I know little about the school, but this area is all noted as part of the Milton Hill School District on early 20th century maps.
John, Joseph, and Will Terry were all sons of William S. Terry, and grandsons of James T. Terry. Another son of James T. Terry was James Francis Marion Terry, noted in the article above as one of the Civil War survivors. JFM Terry's son Isaac Terry built a frame house to the east, on the east side of the Roxboro Road.
In 1922, Isaac "by popular demand" built a dance hall across Roxboro Road from his farm, called the Clover Hill. People would come from miles around to dance at the club.
Clover Hill Club
Sons of Joseph Davis Terry - Edsel Terry, John Roland Terry, and Joseph Wyatt Terry - would play together at the Clover Hill as the "Terry Boys" Their older brother William Samuel Terry didn't play, but would work the door and serve as 'bouncer.'
Isaac Terry's son, Isaac "Ike" Terry (Jr.), worked as a caller at the Clover Hill as well. The Club was popular through the 1940s, particularly with soldiers from Camp Butner.
After World War II, a new club was built on land that had belonged to John Wilkins Terry and passed to his son, Sam Terry. Sam farmed the land and ran a dairy - per the Triangle Sertoma Club website, it was built by "all who wanted to chip in."