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 Princess Anne. She talks about the many illnesses in the area, causing the death of Col. Peter Chaille (misspelled Shally), and his daughter. She asks about how the enslaved people from their father's estate will be split among the family, saying she would like to have Nanny as a lady's maid if it is possible.

Letter from Elizabeth Upshur Teackle to her sister Ann Upshur Eyre, written from Princess Anne. She talks about her bout with the ague, and a picture of Ann that Littleton D. Teackle is sending from Philadelphia. She inquires to health of John Eyre and Sarah Eyre Lyon, his sister. She mentions Sarah Corbin Cropper Wise, Henrietta Teackle, Col. Waters and Susannah Gore 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 from her Uncle Littleton Upshur's home Vaucluse on Hungars Creek. This letter covers Ann's anticipated arrival in preparation for Elizabeth's wedding to Littleton Dennis Teackle. People mentioned in the letter include Betsy Snead, James Lyon, Valeria Spencer Fullerton, and Aunt Ann Parker Upshur.

Letter from Elizabeth Upshur Teackle to her sister Ann Upshur Eyre, written from her Uncle Littleton Upshur's home, Vaucluse, on Hungars Creek. She discusses plans for her upcoming wedding, and mentions her Aunt Ann Parker Upshur and cousin Juliet Upshur.

Letter from Elizabeth Gore Upshur to her daughter Elizabeth Upshur Teackle while she was attending school in Snow Hill, Maryland.

Letter from Elizabeth Upshur Teackle to her sister Ann Upshur Eyre, in which she discusses Dr. Hugh Ker and his unsuccessful run for the assembly.

Letter from John Eyre to Elizabeth Upshur Teackle regarding an injury sustained by her sister Ann Upshur, his future wife.

Letter from Elizabeth Upshur Teackle to her sister Ann Upshur Eyre, undated. The date of this letter is either April or May of 1799 due to context. The letter mentions the long awaited return of the ship Delaware, captained by John E. Sword from Canton. It discusses the wedding of Sarah Corbin Cropper, as well as mentioning Mrs. Vear, Henrietta Teackle, John Teackle, Mrs. John Dennis, Col. Cropper, and Col. Savage.

Letter from Elizabeth Upshur Teackle to her sister at Ann Upshur Eyre, sharing family news from the family home of her Uncle Littleton Upshur's home Vaucluse on Hungars Creek. People mentioned in the letter include Aunt Ann Parker Upshur, Juliet Upshur, Elizabeth "Betsy" Snead, and Dr. Hugh Ker.

Letter from Elizabeth Upshur Teackle to her sister at Ann Upshur Eyre, sharing family news from the family home of her Uncle Littleton Upshur's home Vaucluse on Hungars Creek. She discusses her engagement to Littleton Dennis Teackle, which is still a secret at this time, and mentions people such as Henrietta Teackle, Elizabeth Bowdoin McCroskey, her cousin Juliet Upshur, Betsy Snead, Uncle Littleton Upshur, John Teackle, and the home Eyreville.

Letter from Elizabeth Upshur Teackle to her sister Ann Upshur Eyre while Ann attended boarding school in Philadelphia with Mrs. Valeria Fullerton. The letter touches on family news, their Upshur cousins Leah and Juliet, and other family acquaintances.

Letter from Andrew D. Campbell to Elizabeth Upshur Teackle. He teases her about flirting with boys in Virginia, discusses their shared acquaintances, including Henrietta Liston, wife of the British Prime Minister to the U.S. He talks about his family and the news of the wedding of Elizabeth's cousin Sarah Custis Handy to Ephraim King Wilson. He also talks about the marriage of Anna Teackle Smith to John Donnell of Baltimore and his dislike of her husband. He discusses the death of George Washington: "With you, I grieve for the loss your country has sustained in the death of your great Hero. Few are the ages that produce such characters, but we shall hope, as America is yet in her infancy, that she will produce many who will emulate him. Imagination can hardly picture one to surpass him. It is also a matter of consolation to reflect that he died in the zenith of his glory, in the possession of the noblest faculties of man to his last breath, and without experiencing any of those vicissitudes to which human nature, particularly in the high ranks of life, are so subject. In how few nations do we find men distinguished by their …

Letter from Ann Upshur Eyre to her step-father, John Upshur of Brownsville, written while Ann attended boarding school in Philadelphia. The letter discusses family news, health issues and upcoming nuptials for John Upshur.

Letter from Elizabeth Upshur Teackle to her step-father, John Upshur of Brownsville, from Philadelphia. She writes of her sister and her opinions of society.

Letter from Elizabeth Upshur Teackle to her sister Ann Upshur Eyre, written from her Uncle Littleton Upshur's home, Vaucluse, on Hungars Creek. She lists off the expected guests at her upcoming wedding to Littleton Dennis Teackle: the family of John Teackle, Congressman John Dennis and his wife Eleanor Jackson Dennis, her brothers, Nancy Read, Peter Hack, Dr. George Teackle, her step-father John Upshur of Brownsville, Littleton P. Townsend, Betsy Teackle of Craddock, Maria Parker, and the family of her Uncle Col. Samuel Handy.

Letter from Elizabeth Upshur Teackle to her sister Ann Upshur Eyre, written from Princess Anne. She announces the birth of her daughter, Elizabeth Ann Upshur Teackle.

Letter from Susannah Gore Kendall to an unknown person, possibly Littleton Dennis Teackle.

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 Ann Eyre to her sister, Elizabeth Upshur Teackle.

Letter from Juliet Upshur to her cousin, Elizabeth Upshur Teackle, whom she calls Betsy.

Letter from Ann Upshur Eyre to her sister, Elizabeth Upshur Teackle, written from Eyre Hall, discussing a party of the Taylors coming from Norfolk, along with Robert Barraud Taylor, a Mr. Tilghman, Mr. Morris, and Mr. Jones. Also mentioned are Grace Duncombe Taylor, Retta Teackle of Easton, and John Eyre. The last page(s) of the letter are missing.

Letter from Elizabeth Upshur Teackle to her husband, Littleton D. Teackle, detailing delays in her journey home. She stopped at Dr. Winder's due to a lame horse, and is slowly making her way home. She's heard that a schooner matching the description of one of their boats, the Princess Anne, was seen in the Wicomico river, returning from the West Indies. She says she recently wrote him by Robert Barraud Taylor, who was to post it in the Western Shore mail. She says Grace D. Taylor Eyre just had a boy who is doing well, and that Comfort Winder is also pregnant.