During the Siege of Boston, the New England Army formed from the militiamen who answered the alarm on 19 April 1775 (who became the Continental Army when it was established in June 1775) effectively contained British troops within the boundaries of Boston, and, after the Battle of Bunker Hill, to the peninsula of Charlestown. Many residents moved out of Boston, and some Loyalists from the surrounding countryside moved into town. Conditions within the town were harsh for all who remained; although the British maintained control of Boston Harbor, provisions dwindled within the town while they waited for supply ships to arrive.

Cheever's manuscript diary commences with an entry dated 19 May 1775 in which he writes that he returned to Boston after safely relocating his mother and sisters to Taunton, Massachusetts.  Cheever's succinct entries cover the realities of living through a long military campaign. He describes press gangs and imprisonments within the town on 19 June (on page 2) as "the usual consequence of martial law." His diary entries describe raids and vandalism committed by both sides (see entries for 30 May, 12 July and 9 January), bombardments (2 August, page 4) and the scarceness and expensiveness of food (12 August, page 5).  He also describes the Battle of Bunker Hill in his entry for 17 June (on page 2) and the damage the British troops did to the Old South Meeting House (15 November, page 7).  Cheever's final diary entry describes the last day of the Siege, 17 March 1776 (page 12) and records that General Howe and the British troops left town "upon which the Continental Army enter'd it."

The British were forced to evacuate Boston after George Washington, commander of the Continental Army, seized and fortified Dorchester Heights, just south of Boston, on the night of 4 March 1776 and from that location positioned cannon aimed at British ships anchored in the harbor. The artillery deployed by Washington had been captured from Fort Ticonderoga and Crown Point and laboriously brought from Lake Champlain to Boston by Henry Knox and his men during December 1775 and January 1776.

Who was William Cheever?

William Cheever was born in Menotomy (now Arlington), Massachusetts, in 1752.  His parents, William Downes Cheever and Elizabeth Edwards Cheever, were members of the First Church in Boston.  He attended Harvard College and graduated with the class of 1771.  After college he worked as a merchant for his father's business both in Boston and then in Amsterdam.  By 1784 he was back in Boston and purchased property there (on Battery and Commercial streets). He died in 1786.