Siege Story: Nathaniel Ober

For the soldiers of the Continental Army besieging Boston from 1775-1776, some of the most useful instruments of war were neither the smoothbore musket nor a flintlock pistol, but rather the humble shovel and pickaxe. Aside from the barely two-hour Battle of Bunker Hill and a handful of other minor skirmishes at Grape Island and Chelsea Creek, the Siege of Boston largely stood at a stalemate when General George Washington formally assumed command of the Continental Army in Cambridge on July 3, 1775. As a result, the primary duty of the Continental Army’s estimated 15,000 soldiers was building, guarding, and improving a vast network of fortifications and entrenchments, both north and south of the Charles River, to keep the British Army bottled up in Boston.

For soldiers such as Nathaniel Ober, a former shoemaker serving in John Mansfield’s Massachusetts Regiment, commands to defend or fortify were not uncommon. Starting in May, Ober documented his activities as a soldier in a diary. A week after the British victory at Bunker Hill, Ober reported, "our regiment began to entrench" in Cambridge.[1] Two months later on August 16, Ober wrote, "our people went to Moldon [Malden] to entrench," followed 11 days later with "last night there was about 6,000 men went to Ploud [Plowed] hill and entrenched there." As exciting as these maneuvers might initially indicate, for Ober each one proved to be nothing more than a "false alareme [sic]."

Indeed, the direst foe faced by Ober was tedium. "Nothing remarkable today," is his most repeated entry, which is ironic considering he titled his diary "Nathaniel Obers Remarkable Book." When not on duty, Ober returned to his professional training and kept busy mending shoes, likely for other soldiers.

However, large numbers of soldiers faced boredom, anxiety, and homesickness. Their lack of training meant they were also largely undisciplined. Ober regularly detailed instances of troublemakers who faced punishment. "One man whipped 78 lashes for sundry crimes," he wrote on June 30. In that same week, Ober mentioned how three soldiers, either guilty of desertion or abusing an officer, "rode the wooden horse." This "wooden horse" was a sawhorse-like bench that forced them to sit straddling an uncomfortable wedge-shaped point. Sitting on one for an extended period could be remarkably painful and humiliating. Other offenses Ober mentioned include stealing, disturbing public prayer, failure to report for duty (including an officer), theft, and even a woman "decked for her wanton behavior," potentially one of the many camp-followers.

Despite the absence of large battles, Ober mentioned smaller examples of troop attrition that occurred on the static front lines. On July 6, "a french [sic] man Desarted [deserted] from us and went to the Regelors [Regulars]." More tragically, on August 17, Ober referred to "one man killed on picket by our own people for not answering when he was hailed [.] I saw him brought up this morning a lifeless corpse, he was commended by the general for his good behavior." Disease also took a toll; Ober reported that 12 soldiers alone died within a week in early June. These instances reminded soldiers of the ever-present likelihood of a sudden and unexpected death.

Once the British Army evacuated Boston, Washington’s Continental Army relocated to New York, and the laborious prospect of constructing new defenses on Manhattan and Long Island began all over again. Ober’s continued role in the conflict is unclear – his description of army life ends in February 1776. Ober survived the war, and his diary was later repurposed as an account book.

As a surviving primary source document, Ober’s diary, while lacking detailed accounts of military action or deep introspective musings on the meaning of revolution, nonetheless preserves an unvarnished look into the perils, follies, and challenges of a soldier’s daily life on the front lines of the Siege of Boston.

Footnote

1] This and all following quotes come from: “[Nathaniel Ober diary, 15 May – 3 September 1775, with accounts and notes, 1776 – 1781,” Collections Online, Massachusetts Historical Society. Accessed January 2026.

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