A few scattered letters to Colonel Simeon Potter and William D'Wolfe, believed to be ancestors of the DeWolf family.

Chiefly letters to Nathaniel Russell Middleton from Alicia Middleton, his mother, when he was away from home in Geneva, New York; New York City; Philadelphia; and Liverpool, England. In Geneva, Middleton was attempting to enter Geneva College. His mother wrote about family events and also gave him religious and personal advice on such subjects as controlling his temper and overcoming indolence. In a letter, dated 9 September 1830, Alicia described a recent election in Charleston.

Chiefly letters to Middleton from friends and family. Included is a letter in 1834 from his friend, Lewis Morris, about the sale of a horse. His brother, Izard (Ralph Izard), also wrote in 1834 while he travelled in Philadelphia and New York, and mentioned seeing Fanny Kemble perform.

Beginning in 1839 there are letters directed to and from Annie DeWolf prior to her marriage to Nathaniel Russell Middleton. Included is a letter dated 1842 in which she described a party she attended in Boston where she apparently met Charles Dickens.

In 1842 numerous letters were sent to Middleton congratulating him on his engagement and marriage to Annie DeWolf. His brother, Izard, wrote about this and also about family news and managing the plantation, "Bolton-on-the-Stono."

Chiefly letters between Annie and Russell (Nathaniel Russell) Middleton when she spent the summers in Rhode Island with the children, and letters between the Middleton family and Annie's relatives in Rhode Island. Also included are some letters from friends and relatives in South Carolina.

The letters chiefly refer to family events and activities. Important events in the lives of family members are mentioned, such as the engagement of Annie's sister, Abby, in October and November 1843, the marriage of her sister, Cecilia, in January 1849, and the death of three young daughters of Annie's brother, William, in September 1853. Annie's father died in October of 1857 and letters of condolence and letters referring to arrangements made after his death are included. Ordinary events are also described such as illnesses of family members and remedies used to cure them, arrangements for the trips between South Carolina and Rhode Island, normally made by boat, and arrangements Annie made to house the family when they were in Rhode Island.

From 1856 on, letters from Annie and Russell's children became more frequent. Maria and Annie (daughter) corresponded with their father, who was in Charleston, while they were in Rhode Island, giving news of their daily activities.

A few items of news about the plantation, Bolton-on-the-Stono, are included. In a letter dated 5 July 1843, Russell's brother, Izard (Ralph Izard) told him of land which was up for sale on the borders of "-Stono". In a letter dated 9 June 1845 Annie wrote to Russell about the death of an enslaved carpenter at Stono and the question of who would be trained to replace him.

Russell received letters from his friends Lewis Morris and Henry D. Lesesne. Lesesne wrote letters during the summer of 1849 about his wife's illness and the difficult summer he was having. In a letter dated 16 July 1849, Lesesne described an insurrection led by enslaved people who were in the Charleston work house.

Annie and Russell occasionally mentioned political troubles arising between North and South. In a letter dated 6 August 1852, Annie described reading Uncle Tom's Cabin and feeling she ought to give up her rights to slaves. In a letter dated 1 October 1860 Russell wrote that he did not think that the South could be united over the issue of Lincoln's election to the presidency and that efforts to unite it should wait for some larger issue.

In 1857 there were a few letters congratulating Russell on his election to the presidency of the College of Charleston.

Very few letters were received during the war years from Annie's relatives in the north and Annie and the children were unable to spend their summers there. What letters were exchanged mentioned unhappiness at the separation and the difficulties of getting letters to each other. Occasionally, Annie mentioned supply shortages in the South. In a letter dated 19 September 1864, Annie requested that mother send her a quarter of an ounce of quinine. She wrote that the ships brought in quinine but that it was immediately sent to the army even though in the Charleston climate it was necessary to have quinine for fever.

The family apparently resided in Summerville, South Carolina, during the war. In 1863, one of the children, Maria, visited relatives in Darlington, South Carolina and sent letters describing her activities. In 1864, Annie also went to Darlington for her health. Other correspondents include J. Francis Fisher, apparently from the North, who sent a letter to Russell dated 27 November 1864 about sending Russell's son Henry to him on a boat with some southern prisoners of war to be exchanged.

Chiefly letters between members of the immediate family after the war. Many of the letters deal with the various business enterprises the Middleton family entered to support themselves, and the difficulties they experienced. In 1868, Annie began, with a number of other women, the Carolina Rice Company, which advertised rice and other goods for sale. A letter dated 25 June 1869, written by Annie, appears to be a rough draft of a letter to Adolph Bovie, Secretary of the Navy, asking him to purchase rice for his ships from their company. Russell periodically mentioned difficulties the college experienced and his efforts to secure the salaries of the professors. In 1870 there are several letters from Arthur Middleton to his father, Russell, about his financial troubles in the rice business and asking for a loan. At the end of 1870 and the beginning of 1871, there are numerous letters between Nathaniel Russell Middleton, Jr. and his parents about his attempts at entering the phosphate fertilizer business.

Also included are numerous letters between Annie (daughter) and her friends.

Chiefly family correspondence describing ordinary family activities. Letters were exchanged when some members of the family were in the North and others in the South. During the summers, Russell Middleton stayed in Charleston, frequently with one of his daughters, apparently taking care of college business, while Annie was in Rhode Island. The subseries ends the year Russell retired as president of the College of Charleston.

Continuing family letters. There is less correspondence between Annie and Russell because they had fewer separations. Annie's brother William, from Chicago, wrote frequently. Some of the letters mention the ongoing problems with the estate of Annie's parents, and the estate of her aunt, Maria DeWolf Rogers. The property left from these estates led to disagreement among the children. In 1886 there are numerous letters from friends and family about the earthquake in Charleston. No one in the Middleton family was hurt, but their house was damaged.

There are only a few letters after 1900. Most of them are directed to Alicia Middleton who lived permanently at Hey Bonnie Hall, near Bristol, Rhode Island, with her mother and her sister Annie. In 1900 Alicia corresponded with Langdon Cheves about an article on the Middleton family he was writing for the South Carolina Historical and Genealogical Magazine

Undated letters and letter fragments of the Middleton family members and others. The letters are arranged by recipient. However, when the sender is identifiable and the recipient is either unknown or not a family member, the letter is filed under the sender's name.