Letter from Elizabeth Upshur Teackle to her sister, Ann Upshur Eyre. She scolds Ann for not responding to her and discusses various family matters. Their brother, Arthur Upshur, is getting married in the next month. Retta wishes to take Elizabeth to Easton and Elizabeth wants to see Ann in Northampton.

Letter from Juliet Upshur Elliott to her cousin, Elizabeth Upshur Teackle. She at length discusses society's views towards men and women, and how women are treated by men. She also talks at length about family matters, mentioning a variety of relatives, including Littleton Upshur, Abel Upshur, Caleb Brown Upshur, Ann Upshur Eyre, Arthur Upshur, Retta Teackle, Leah Curtis Upshur, and Eleanor "Nelly" Jackson Dennis.

Letter from Elizabeth Upshur Teackle to her sister, Ann Upshur Eyre. She asks Ann to write back to her, and she mentions she grows tired at managing her own personal affairs alone, especially with her husband out of town. She also discusses attending the wedding of Miss Anne Denwood and Mr. Barns with Retta and mentions their cousin John.

Letter from Ann Eyre to her sister, Elizabeth Upshur Teackle.

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.

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.