The collection of photopied copies of family correspondence spans the years between 1828 and 1894. A number of the earlier letters are copies of typescript copies made by the donor. The letters written by each member of the family are filed separately. Letters to family members from persons outside the family are filed with letters written by the recipients.

Lavinia Hobart Pillsbury's letters to her children run from 1836 to 1871. Of particular interest is her description of a meeting with an escaped person who had been enslaved headed for Canada, dated April 9, 1850.

Four of Reverend Stephen Pillsbury's letters are in the collection. They run from 1828 to 1841.

Josiah Pillsbury's 29 letters run from 1840 to 1871. His letters to relatives in New Hampshire from 1854 through 1858 describe emigration and settlement in Kansas.

The 12 letters of L. Hobart Pillsbury to his mother and sisters run from 1856 to 1889. They describe his emigration to Kansas with Josiah in the 1850s and his Civil War service.

The collection contains five letters of Edwin Pillsbury from the 1850s. As a sailor, he had little contact with his family, and the letters describe the poverty that prevented him from joining his brothers in Kansas.

Nine letters of William Pillsbury to his brothers and his sister Lavinia run from 1853 to 1869.

Stephen Pillsbury's letters run from 1840 to 1892. His letters from the 1840s describe his and Josiah's efforts to start a business in New York City.

Mary Pillsbury Weston's letters run from 1840 through 1894. They cover New York City's cholera epidemic of 1854, the financial panic of 1857, and the Civil War years in the city.

Anne Pillsbury Marshall's letters run from 1841 through 1855. Her letters cease before her emigration to Kansas in 1855.

The correspondence of Lavinia Pillsbury Andrews runs from 1837 to 1871. She was the most active correspondent in the family, keeping in touch with the entire family and a number of friends. Her daughters Sarah and Anne were also active correspondents. Sarah's letters run from 1869 to 1894. Sarah wrote most of her letters to her parents and sister while at school in Concord, New Hampshire from 1869 to 1871. Anne's letters to her parents and sister run from 1871 to 1888. Eva Weston kept up an active correspondence with her cousin Sarah Andrews from 1865 on. Many of her letters describe her life in Lawrence, Kansas after 1874.