Letters written to J. Dorr Waterman (1835-1883) make up most of this collection. The letters were written by five different young women between 1851 and 1860. The letters reveal that Waterman had close relationships with these women. They often express how they miss him, wish to see him, and enjoy his company. It is also clear from these letters that Waterman traveled back and forth between his birthplace in Le Roy, Genesee County, New York, and Kalamazoo many times before and after permanently settling there in 1857. Three of the women were residents of New York, near Le Roy, and two lived in Kalamazoo. Mary “Mollie” Whipple (1836-1854) of Riga, New York, wrote 28 of the letters from 1851-1853. Her last letter, dated October 1853, reveals that she was suffering from an illness and embarking on a journey to New York City for treatment. Hattie [Fiske?] (unknown birth and death dates), a resident of Stafford, New York, wrote 12 letters between 1854 and 1855; Sophie Cash (1834-1932) of Le Roy, New York, wrote two undated letters; Jane Drake (1826-1899) of Kalamazoo wrote two letters in 1860; and Maria Drake (1836-1883) of Kalamazoo wrote one undated letter. Maria Drake married Waterman in 1866, but it is unclear if her letter was written before or after their marriage.

Another large portion of this collection is made up of correspondence and financial records of Waterman’s mother, Mary C. Simonds (1813-1868), and her second husband Darwin Simonds (1812-?). Much of the correspondence concerns a lawsuit the Simonds brought against a man named Kellogg. Most of the financial records are receipts for items Mary Simonds purchased both before and after her marriage to Darwin Simonds.

The items related to the Civil War include two letters written by a union soldier, a certificate for stock purchased in the Soldiers and Sailors Association, two mail-order copies of the Gettysburg Address, a small reproduction of a photograph of Abraham Lincoln, and a mail-order form for purchasing Lincoln-related material. The letters detail the uniform the soldier wore, the death of another soldier, and camp conditions. It is unclear if or how these items relate to Waterman or Simonds.

Advertisements and tax receipts for Kalamazoo and Van Buren Counties make up the final part of this collection. The items date roughly from 1874 to 1903. The ads include material for Kalamazoo area hotels, the Lynch Bros. Dry Goods store of Kalamazoo, and H. Stern and Co. Clothiers of Kalamazoo. The tax receipt is for property owned in Van Buren County in 1874. There are also three letters written to residents of Kalamazoo and Van Buren Counties, including Dr. Charles Maynard (1830-1910) of Paw Paw. It is not clear if or how these items relate to Waterman or Simonds.