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

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