During the American Revolution, Nova Scotia was invaded regularly by American Revolutionary forces by land and sea. Throughout the war, American privateers devastated the maritime economy by raiding many of the coastal communities. There were constant attacks by privateers, which began seven years earlier with the Raid on St. John and included raids on all the major outposts in Nova Scotia. The first raid on Chester happened in 1779 and the second happened three years later.
Raid on Chester
On June 30, the day before the raid on Lunenburg, Stoddard and two other privateers descended on Chester, Nova Scotia firing cannon from their vessels. Captain of the militia Jonathan Prescott fired cannon from the blockhouse Prescott's cannon fire struck one of the privateers. As a result, the privateers retreated behind Nass' Point. The crews went ashore and requested of Prescott to bury their dead. Prescott indicated that if they disarmed themselves, they would be assisted. Eventually, Prescott invited Stoddard and the two other captains to tea. Realizing the community was still vulnerable to attack, Prescott and his son lied to the privateers that Commander Creighton at Lunenburg had sent 100 soldiers to be billeted at Chester that evening. Upon the privateers retreating to their vessels, Captain Jacob Millett led women and children marching in red colours, pretended to be British soldiers from Lunenburg. The privateers left Chester to raid Lunenburg the following day.
Afterward
The day after the raid on Chester, the American privateers redirected their attack on Lunenburg, presumably believing the Lunenburg militia had left the town to defend Chester. Prescott was suspected of being an American Patriot sympathizer given that, after the initial hostile engagement, Prescott reportedly allowed Captain Noah Stoddard to bury his dead and then had tea with him the day before Stoddard orchestrated the Raid on Lunenburg. People were also suspicious of Prescott's allegiance because a number of Dr. Prescott's family were Patriots in the American Revolution. His nephew Samuel road with Paul Revere. Samuel eventually was taken prisoner to Halifax where he is reported to have died during the war. Jonathan named one of his son's after his nephew Samuel and he is buried in Old Burying Ground. Jonathan's son Joseph joined the Continental Army, fought at Fort Ticonderoga and was a founding member of the Society of the Cincinnati. Another of Dr. Prescott's sons John fought in the Battle of Lexington. His other son was Charles Ramage Prescott. After the war, Prescott was given the blockhouse and used it as his home.
