According to a story published in the 1840s by historian Dr. Jeremiah Spofford, Cuffee was born free in Boston. His mother left him as an infant in the care of a woman in Tewksbury named Trull, so she could continue working. The deceitful woman, not wanting to care for him anymore, sold him when he was about 3 years old to Captain Moses Dole of Rowley West Parish (now Georgetown) and told his mother that he had died. Years later, when Cuffee was around 25, Mrs. Trull, on her deathbed, sent for him and confessed what she had done to clear her conscience. When Cuffee told Mr. Dole the story, he was granted his freedom, although he remained with the Doles until enlisting in the American Revolution.
But is this story true? Our church historian went in search of the facts.
Cuffee gave his age as 32 in his enlistment papers in 1780, which would put his birth around 1748. Although there were a number of black children named Cuff of Cuffee (slaves were not given surnames) born in the Boston area around that time, one stands out. Records show that a black child named Cuff, belonging to Sergeant Trull of Tewksbury, was baptized on 11/12/1749.
Cuffee was raised on Major Dole’s 100-acre farm on Baldpate Hill, along with a large family of children around his age.
Moses and Ruth Dole already had four children when Cuffee arrived and would have four more in the coming years (we wonder what Mrs. Dole thought when her husband brought home another child for her to raise). He was treated much like a family member, eating, sleeping and doing chores with the other Dole children. But unlike the others, he had to address Moses and Ruth as Master and Mistress Dole.
But did Major Dole just give Cuffee his freedom after hearing of Mrs. Trull’s death-bed confession? In the Last Will and Testament of Moses Dole, dated 2/14/1772, he states, “I give unto my Negro man Cuff and Negro woman Chloe the liberty to live with any one of my children after me and my wife decease.”
It certainly sounds like Cuffee was still considered a slave, although Mr. Dole’s will may have been written before hearing the story of Cuffee’s birth. After Mr. Dole’s death later that same year, the inventory of his estate included a “Negro woman” valued at 33.6.8 (pounds, shillings, pence) but no “Negro man.”
However, on the list of people owing money to the estate is “Cuff, a negro, for 20.6.89.” It appears that he was allowed to purchase his freedom. Cuffee remained with the Doles until marching off to fight in the American Revolution. It was at this time, as a free man, that he chose the surname of Dole.
Like many other men in our community at the time, Cuffee Dole fought in the American Revolution, enlisting not just once or twice, but three times! The earliest record found shows that Cuffee was on Prospect Hill in Cambridge in March of 1776 during the siege on Boston. He was there when General George Washington ordered the construction of fortifications at Dorchester Heights, along with the installation of cannons capable of reaching the British ships, which caused the British to flee on March 17th (this is why St. Patrick’s Day is also called Evacuation Day in Boston).
Cuffee enlisted again, along with 21-year-old Peabody Dole (son of Cuffee’s former owner) on August 15, 1777, in the Rowley Militia with Captain Benjamin Adams’ regiment, under the command of Major General Benjamin Lincoln. Cuffee was put to work as a servant for Lincoln and often related that he was washing the Major General’s clothes on the banks of the Hudson River when he heard the thundering of artillery as the second battle of Saratoga began. This was the first major victory for the Patriots and a turning point of the war. Cuffee and Peabody Dole were among the 20,000 Patriot soldiers who surrounded Saratoga, where British General Burgoyne and his 6,000 soldiers had retreated to and were there when Burgoyne surrendered on October 17, 1777. Cuffee and Peabody were discharged on November 30, 1777, and returned home.
In 1780, General George Washington put out a call for new recruits in the dwindling Continental Army, and Cuffee once again answered the call, marching from Rowley on July 6, of that year.
Washington’s army, including Cuffee, were encamped on the hillsides around Tappan, NY, where they witnessed another historic event. On October 2, 1780, British Major John Andre, who had conspired with the infamous traitor Benedict Arnold, was hanged as a spy at high noon in front of the assembled troops.
Cuffee was discharged from the Continental Army on December 14, 1780. Though the war continued for three more years, Cuffee’s time in the army was over.