The strengths of Webb's diaries are his ability as a writer and his willingness to describe important incidents at great length. His descriptions range widely in content, but are always thoughtful, and he has a flawless aptitude for an anecdote. He seems particularly to have been interested in the attitudes of his fellow soldiers and of local civilians, particularly the women, but he comments extensively on daily life in the camps, strategy, officers, drilling, ethics in the army, and his feelings, positive and negative, towards those who remained in Maine. Webb's careful and detailed descriptions of every battle and skirmish in which he was involved include everything from vignettes relating an individual soldier's reactions, to specific information on the tactics and strategy of cavalry. But it is the incidents he records about day to day life that provide the greatest insight into the soldiers' minds, and Webb is both uncommonly detailed for a Civil War diarist and allows his personal opinions and perspective to dominate his descriptions. His description of Belle Isle is extraordinary in the intensity of detail and emotional impact.
These five volumes are copies from the original diaries, and were made by Webb in the late spring and summer of 1865. He notes that, with the exception of some additions made from memory to his descriptions of Libby and Belle Isle Prisons, he has copied the diary exactly as it appears in the original. Offering an interesting balance to the original, he includes occasional footnotes offering retrospective commentary on his own writing. For example, while in 1862 he wrote that the men were upset at the dismissal of McClellan, a footnote indicates that in 1865, Webb came to feel that the men had been deluded by McClellan's self-aggrandizing play for their affection. His later comments on his own vacillation while deciding whether to reenlist, on the opinions of the media and non-combatants regarding the war, and on his opinions of Meade and other leaders also include some revealing reflections.
The first fifty pages of volume 3 are severely damp-stained and written in faint ink, and in parts are very difficult to read. Included with the diaries are an 1878 receipt for the payment of poll tax in Boston and one issue and two supplements of the First Maine Bugle (Campaign II, call 3, 5 and 9), dated January and July, 1891, and July, 1892. The Bugle was the publication of the veterans' organization for the 1st Maine Cavalry. A war-time photograph of Webb was included in Tobie's regimental history.