Letter from Elizabeth Upshur Teackle to her sister, Ann Eyre, written from Princess Anne. This letter discusses her sister-in-law Sarah Upshur Teackle Bancker, and some family unrest over a man who was courting her behind her parents back, George Wilson Jackson. While in New York City, she met Charles Nicoll Bancker, her eventual husband, and this letter explains how it all came to pass. George Wilson Jackson was the brother-in-law of Congressman John Dennis, Littleton Teackle Dennis's Uncle who lived next door to them in Princess Anne at their home Beckford, which Elizabeth states "places our family in a delicate situation." Elizabeth mentions a recent trip to Baltimore and their Aunt Susannah Kendall.

Letter from Elizabeth Upshur Teackle to her sister Ann Upshur Eyre, written from her father-in-law John Teackle's home, Kegotank. She shares family news and mentions her friend Dolly Harwood, Elizabeth Dennis Teackle, Ann Parker Upshur, Mr. Evans, John Eyre, and her husband's sisters Henrietta and Sally.

Letter from Elizabeth Upshur Teackle to her sister Ann Upshur Eyre, written from Philadelphia. She mentions see various friends in town such as Paschall Hollingsworth, Mr. Davis, and Ben Wilcocks, and members of the Teackle family..

Letter from Nancy Cunningham to Sarah “Sally” Teackle Kendall describing her flight from Philadelphia during the Revolutionary War, and also contains updates about Teackle's brother Severn Teackle who is imprisoned by the British on a ship anchored off Long Island. Severn Teackle is the Grandfather of Severn Teackle Wallis. Attached to this letter is a note dated 1829 written by Elizabeth Upshur Teackle explaining how she came to be in possession of this letter from her Great Aunt Sally Teackle Kendall.

Letter from Andrew D. Campbell to Littleton Dennis Teackle before their journey back to England. Campbell was from Glasgow, and a classmate of Teackle's at Columbia University.

Letter from Elizabeth Upshur Teackle to her sister, Ann Eyre, written from Kegotank. She discusses the arrival of a fancy wig for Ann from Philadelphia which cost $26. She shares news of the death of Abel Upshur Teackle.

Letter from Elizabeth Upshur Teackle to her husband, Littleton D. Teackle, updating him on their travels to his father John Teackle's house. She says they visited Major Carroll and will be setting out in the morning for Northampton. She also discusses her health and the death of Samuel Lippencott.

Letter from Thomas R. Joynes to Littleton D. Teackle.