Throughout the war, American privateers devastated the maritime economy by raiding many of the coastal communities.

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.

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' retreat to their vessels, Captain Jacob Millett led women and children marching in red colours, pretending to be British soldiers from Lunenburg.

[8] Jonathan's son Joseph joined the Continental Army, fought at Fort Ticonderoga, and was a founding member of the Society of the Cincinnati.