His first book was a "History of Western Massachusetts". He followed in 1857 with an historical novel, "Bay Path", and a collection of essays entitled "Titcomb's Letters to Young People, Single and Married" in 1858. In 1862, when Samuel Bowles took an extended trip to Europe, Holland temporarily assumed the duties as editor-in-chief of the "Springfield Republican". After the Civil War he reduced his editorial duties and wrote many of his most popular works, including the "Life of Abraham Lincoln" (1866), and "Kathrina" (1867).