Piedmont Historic Homes

1939 N.C. Highway 57 N., Milton, Caswell County
Woodside, the Caleb Hazard Richmond House
National Register of Historic Places

• $595,000
• 5 bedrooms, 5 1/2 bathrooms, 4,400 square feet, 5 acres
• Price/square foot: $135
• Built in 1838
• Listed January 19, 2022
• Last sale: $75,000, December 2021
• Note: The property is under protective easements held by the Historic Preservation Fund of North Carolina.
  • Woodside had fallen into serious disrepair by the time it was nominated for the National Register in 1985. In the 1990s, it was restored as a bed and breakfast and restaurant, which operated as recently as three years ago.
  • The house is about two miles southeast of Milton.
  • Listing: “Thomas Day Staircase.” News & Record, April 18, 1995: “Woodside is filled with beautifully executed woodwork attributed to Thomas Day, Milton’s free black craftsman. A fine example of the workmanship is the mahogany staircase railing which ends in a nautilus-shaped swirl.”
  • National Register nomination: “Woodside, the home of Caleb Hazard Richmond in northeastern Caswell County, is a splendid … example of Greek Revival residential architecture produced during the county’s ‘Boom Era’ in the middle decades of the 19th century.
  • “Standing on its elevated site some 2 miles east of the small town of Milton, Woodside overlooks the surrounding countryside that produced the bright-leaf tobacco which was the mainstay of the county’s economy during that boom period. …
  • “The large house was once the seat of a plantation consisting of 350 acres and was probably built in the late 1830s, shortly after Richmond married his second wife, Mary R. Dodson, and within a few years after he had made his first land purchase in the county.
  • “Although only 5 of those 350 acres are now associated with the house and only one of the numerous outbuildings which supported the household survives, Woodside remains as a vivid reminder of the prosperity which characterized the county during the period from the late 1830s until the Civil War.”
  • “Typical of the substantial houses constructed in the county during the period, Woodside is a large dwelling of simple vernacular form finished with well-executed pattern-book Greek Revival details.
  • “The fine interior woodwork, including the distinctive scrolled staircase newel and bowed parlor mantel flanked by niches, is attributed to Thomas Day. Day was a superior craftsman and free black who operated a furniture-making shop in nearby Milton and is credited with creating many of the county’s finest interiors during the ‘Boom Era.’
  • “It was at Woodside that the Confederate officer (later general) Dodson Ramseur met, courted and married (1863) Ellen Richmond, daughter of Caleb.” Dodson and the soon-to-be-widowed Ellen were cousins.
  • Dodson was from Lincolnton. Although much is made of his connection to the house, he stayed there only briefly during the war, including some months while recovering from wounds. A roadside plaque on the property is devoted to him, put up by the Daughters of the Confederacy and the “Military Order of Stars and Bars.”
  • A laudatory article on Dodson in America’s Civil War magazine recounts his “conspicuous gallantry,” “magnetic leadership” and victories in battle but also notes his “unaccountable lapses,” staggering numbers of his troops being “slaughtered,” poor decisions, mistakes, and rashness. He ultimately died as a prisoner of Union generals Sheridan and Custer after after attracting heavy fire as one of the conspicuously few men on horseback during an October 1864 battle in the Shenandoah Valley. His only child, Mary, had been born four days earlier.
  • The Caswell County Historical Society relates the sad consequences for his family: “Ellen Ramseur never remarried and wore black mourning clothing for the rest of her life. She remained with her family in Caswell County until she died in 1900 at the age of fifty-nine. Mary Ramseur never married and died at the age of seventy-one in 1935.”
  • Curiously, the civil-war magazine article says, one Dodson’s best friends at West Point had been the same George Armstrong Custer, who ultimately took Dodson prisoner and eventually outperformed Dodson as an author of battlefield catastrophe. “Stephen Dodson Ramseur and George Armstrong Custer were just about as unlike as any two cadets who had ever attended the U.S. Military Academy. Custer, nicknamed Fanny by his fellow cadets, was tall, blond and voluble. A poor but popular student, he chafed at the restrictions and rules at West Point.
  • “Ramseur, on the other hand, was a small, darkly handsome young man whose natural reserve hid an underlying strength of purpose. While not an outstanding student, he applied himself well enough to finish in the top third of the class, and his leadership skills made him captain of cadets.
  • “Deeply religious, he was also a staunch Southerner who, since a Yankee had ruined his father in a business deal, had little use for anyone from the scheming, cold-hearted North. He politely defended states’ rights and the institution of slavery, which he called the very foundation of our existence.
  • “Yet the two cadets had become friends, for they did have more than a few things in common. Both were superb athletes, especially on horseback. And although Ramseur was very religious, he was not an insufferable Puritan like some of the New Englanders, and certainly was not too good to enjoy a joke, a drink or a twist of tobacco.
  • “In short, he was a boon companion and as such was willing to accept Custer, Merritt [a future Union general and cavalry commander] and a few others from his general dislike of Northerners. Wes Merritt thought him one of the most universally beloved men in the class.”