Letter from Ann Upshur Eyre to her sister, Elizabeth Upshur Teackle. She states that she will not be able to visit Elizabeth because of the bad state of the roads and she hears Littleton Dennis Teackle has returned home. She mentions her mother-in-law, Margaret Taylor Eyre, is ill. She says the girls will have to come visit Elizabeth soon and she will send Abel, an enslaved man, with them. She then talks about Elizabeth's finances, local gossip about the Tabb family, and an event in Norfolk. The last page(s) of the letter are missing.
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, in response to a letter about Ann's time in Philadelphia. She talks about enjoying imagining the trip and says she sometimes envies her sister. She mentions how her garden is flourishing and asks Ann to bring her hyacinth roots. She also mentions their shared acquaintances John Brown, Samuel Ewing, Benjamin Chew Wilcocks, Valeria Fullerton, Sarah Eyre Lyon, Eleanor "Nelly" Jackson Dennis, and Elizabeth "Betsy" Snead.
Letter from Elizabeth Upshur Teackle to her sister, Ann Upshur Eyre. She discusses family news, including William Eyre's injury, Arthur Upshur's land purchase, and her daughter, Elizabeth Ann Upshur Teackle's schooling progress. She expresses that she misses Ann and asks her to write back to her.
Letter from Elizabeth Upshur Teackle to her sister, Ann Eyre. She starts by responding to a note Ann sent from Laurel, Delaware. She mentions General Henry Dearborn, who was given the nickname "Granny Dearborn" by his men during the War of 1812. She asks if Ann has seen any of Elizabeth's old friends in Philadelphia, specifically mentioning Sam Evans, Valeria Fullerton, Sally Whiteford, Dolly Heariss, Mrs. Smith, and Mrs. Biddle. She says that her husband Littleton D. Teackle has bought her a new coach and horses. She also visited Amelia Williams Gale, the Carroll's, and Mrs. Jackson. She asks Ann to write her about her stay in Philadelphia and to find talk to Jack Seargeant about the possibility of marrying her daughter, Elizabeth Ann Upshur Teackle. She mentions a fire in Easton, Maryland, and lists some goods for Ann to buy and send to her.
