The collection consists of two letters, an account statement, and a travel journal written by Caroline L. Bowes Kennedy (Carrie). Items date from 1859, 1864, and 1878 to 1879, and are arranged chronologically. The 1879 travel journal comprises the largest portion of the collection.

The two earliest items relate to Carrie’s parents. The first is an account of the estate of Daniel Bowes with Charles Eberle for services rendered at the funeral of Daniel Bowes dated 9 September 1859. On 16 September 1864, F. M. Colburn, ticket agent for the St. Louis, Alton & Terre Haute Railroad, wrote a letter of introduction for Mrs. Bowes as she travelled to Middletown via Cincinnati and Cleveland. He addressed the note to ticket agents and conductors informing them that she was the widow of a railroad conductor and requesting that they be of assistance to her.

On 16 April 1878, Nathan J. Morrison, the first president of Drury College (Springfield, Missouri), provided a letter of reference for Carrie to use as she sought employment as a teacher. In the summer of 1879, Carrie travelled from Springfield, Missouri, to Stroudsburg, Pennsylvania, to visit her paternal grandmother. She described her trip in detail, from June 8 to June 19, and mailed the journal to her family in July. Carrie visited aunts, cousins, and friends in St. Louis. Several of her outings in the city included attending a kindergarten exercise, a moonlight picnic in a garden illuminated by gaslight, and visiting the Fair Grounds and Zoological Gardens. Carrie left St. Louis by train on June 16th for Stroudsburg and described scenes in Illinois, Indiana, and Ohio. After changing trains in Toledo and the cars being switched to boats for the river crossing into Canada, she toured Niagara Falls and the town. Carrie described her tour of the area in much detail.