Letter from Elizabeth Upshur Teackle to her sister, Ann Upshur Eyre. She voices her irritation and scolds her sister for not visiting or writing her, saying Ann missed many events and visitors who would've liked to see her. She also talks of their shared acquaintances Betsey Dennis, Louisa A Bowdoin, Leah Savage, Ann Billings Steele Upshur, Mary Nevett Steele. She says that the health of baby Virginia, daughter of her brother Arthur Upshur and Ann Billings Steele Upshur, is improving. She mentions that Lucy, an enslaved person of the Teackle's, helps breastfeed the baby. The last page(s) of the letter are missing.

Letter from Elizabeth Upshur Teackle to her sister, Ann Upshur Eyre, inviting her to come visit on the 22nd of February. She mentions Louisa A. Bowdoin and the death of General John Gale. She also talks about the war, discussing English squadrons preparing to attack the French fleet.

Letter from Elizabeth Upshur Teackle to her husband, Littleton D. Teackle, updating him on her travels to Northampton County. She says she will head back to Princess Anne the next day. She discusses the possibility of traveling during the summer. She also mentions the death of Thomas Lyttleton Savage.

Letter from Elizabeth Upshur Teackle to her husband, Littleton D. Teackle, updating him on their travels to Northampton to see the Eyre family. She says that Ann and John Eyre are upset because many of their enslaved persons fled to join the British troops. Their slave Jack also died. She says she will be back at home by the next week and also mentions the upcoming marriage between Leah Lyttleton Savage and Harold Luther Wilson.

Letter from Elizabeth Upshur Teackle to her sister, Ann Upshur Eyre, updating her on their return from Ann's house to Princess Anne. Elizabeth says that her husband Littleton has been sick. She also describes how she tripped out of her carriage and hit her head. She discusses how the town is full of military and Major Daniel Martin shared some war stories with her. She also talks about John Nivison.

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

Letter from Elizabeth Upshur Teackle to her sister, Ann Upshur Eyre. She wishes for better health for Ann, John Eyre, Anne Billings Steel Upshur, and Virginia Upshur, as they have been sick. She discusses politics, her daughter, Elizabeth Ann Upshur Teackle's interests, and jokes about receiving an ewe from colonel Wilson. She asks about Louisa Bowdoin and Marry Ann Smith Gilmor's trip to Baltimore and closes with well wishes to friends.

Letter from Elizabeth Upshur Teackle to John Eyre, discussing her health.

Letter from Elizabeth Upshur Teackle to sister, Ann Upshur Eyre. She discusses her health, homesteading tasks, and the process of renting houses to applicants. She mentions Henry Maynardier Murray, and discusses the deaths of Colonel John Done's wife and daughter, Margaret Waters Done and Patience Bayly Done. She asks about Louisa A Bowdoin, Mary Anne Gilmore, and Elizabeth Custis Teackle and hopes for better health for the Eyre family.

Letter from Elizabeth Upshur Teackle to sister, Ann Upshur Eyre. She writes that George Wilson heard from Caleb Upshur that she had written unkind words about a duel Wilson was in. Wilson then went to Mr. Teackle and complained. She asks Ann to be more careful sharing her writing with others and to remember some things should be kept to themselves. She also talks about the health of Anne Billings Steele Upshur and her daughter Virginia Upshur. She says her husband, Littleton D. Teackle will be leaving for Annapolis tomorrow.

Letter from Elizabeth Upshur Teackle to her sister, Ann Eyre. She discusses writing poetry, weaving, raising pigs, and eating a lot of spare ribs. She hopes that the conflict that emerged from her writing is settled with Caleb Upshur and George Wilson. She also provides instructions on how to dye yarn and cotton green. She says that she just returned from visiting her cousin Eleanor Jackson Dennis.