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Some specific matters included in this volume are: visits to the Catskills, West Point and Sing Sing prison (August 1858) and to the New Jersey Palisades (June 1859); a lengthy entry recording a statement by Dr. Elisha Kane to Henry Grinnell regarding Kane's expedition to the Arctic on the ship Advance (October 1858); the demonstration of a safety fuse patented by Gomez & Mills (30 January 1858); celebration in New York City of the laying of the trans-Atlantic telegraph cable (1 September 1858); the first procession of the Sons of Malta in New York (11 October 1859); reception of the Japanese Embassy (16 June 1860); a Zouave Cadet drill (12 July 1860); solar eclipse (18 July 1860); a visit to the ship Great Eastern (26 July 1860); and the visit of the Prince of Wales (October 1860). In addition to the entries, the volume includes leaf tracings, dated autographs (1855-1864), a sketch by Hill of a house, possibly his home (1860), poems, and a family record showing Hill's parents and immediate family members.

Some specific matters included in this volume are: Hill sees Lincoln as he proceeds to Washington DC for the inauguration (19 February 1861); joins the Empire Lodge #64 of Oddfellows, on his father's nomination (November 1861); goes to a "concert saloon" for the first time, describes it, but is appalled and leaves in ten minutes (21 November 1861); Philip's brother Luther enlists in the 34th Regiment (June 1861) and is later killed at Fair Oaks (June 1862); struggles with the Spuyten Duyvel current (4 May 1862); Philip's experiences in the 7th Regiment of the New York State Militia at Fort Federal Hill (July-August 1862), including camp life, drills, disciplinary actions, pranks, and guard/police duties. The volume includes tipped-in clippings concerning Luther Hill's death and Philip's transcription of the last letter Luther sent to his wife Anna, as well as other related items. In the volume is a bookmark with the words "Remember Me"; possibly this is one of the bookmarks given to Hill by Miss Bear (29 April 1862). Also in the volume are leaf tracings, loose clippings, and Civil War-themed envelope images glued in.

Some specific matters included in this volume are: a visit to a Shaker village outside of Albany and a brief description of the rituals (19 July 1863); marriage proposal to Emma Tompson, also referred to as "Puss" in the entries (17 March 1864); visit to the Metropolitan Fair (14-16 April 1864); visit to Niagara Falls (7-8 July 1864); refers to an arrangement for a substitute for him if he is drafted, which proves unnecessary because the quota is met (5 September 1864); reaction to death to Lincoln and visit to Lincoln's corpse at City Hall (April 1865). The volume includes various tipped-in clippings. Hill was in Albany during the 1863 draft riots in New York and so, other than a brief reference to them upon his return, the event does not appear in his diary.