Nathaniel Dickinson (1734-1788) was the third of five children born to Samuel and Hannah (Field) Dickinson of Deerfield, Massachusetts. He and his younger brother, Samuel, jointly owned a farm in the Mill River section of Deerfield, Massachusetts. An active and outspoken Tory, Nathaniel fled to Boston in January 1775 to take refuge with the British army there. He evacuated with the British army to Halifax in 1776 but returned to New York City while it was occupied by the British where he worked with and for the British army until 1783. While in New York, he married Hannah Cock in 1781. The couple had two children, both of whom predeceased their parents. After the war, he settled in New Brunswick, Canada. (Stephen Davidson, "A Violent and Active Tory: The Loyalists of Deerfield", Loyalist Trails 2013-2014, November 10, 2013.)
The Deerfield Committee of Safety and Correspondence confiscated Nathaniel's share of the farm at Mill River and sold it at auction in December, 1776 and he was officially banished from Massachusetts in 1778. Samuel initially was allowed to rent part of the Dickinson farm after it was confiscated but the Massachusetts General Court ordered in 1780 that part of the estate be set aside for “the use of the State for pasturing cattle for the use of the Army.” The proceeds from the auction of Nathaniel's share of the Mill River farm was paid to the state treasury. (George Sheldon, A History of Deerfield (Greenfield, MA: PVMA, 1896) Vol. II, p. 714; "The Fate of Nathaniel Dickinson: An account of a Loyalist from Deerfield, MA", Dickinson Family Association Newsletter, Volume XVII, Number 2.)
In his claim to the British government for compensation for property confiscated as a result of his loyalty to the Crown, Dickinson included "A Negroe Man, taken by the rebel committee, and held in the army worth £50 strg." (Alexander Fraser, ed. United Empire Loyalists: Evidence into the Losses and Services in Consequences of Their Loyalty: Evidence in the Canadian Claims (Toronto: L.K. Cameron, 1904), p. 114.) This was likely Caesar Bailey of Deerfield, who served in both the Massachusetts militia and the Continental Army. The Dickinson brothers shared Cato (also known as Dick Cato,) and Caesar's wife Hagar.
Nathaniel served as a Lieutenant in for the British commissary general in New York during the American Revolution, where he married Hannah Cock. As the war came to an end, Nathaniel joined other Loyalist refugees in New Brunswick, Canada, where he was granted land by the British government. According to Stephen Davidson, an historian of Black loyalists and those enslaved by Loyalist refugees in New Brunswick, Canada, the Dickinsons departed for Canada after purchasing three enslaved people: Jack, aged 38, Betty, aged 20, and Sukey, aged 4. Dickinson never recovered his Deerfield estate and died in Westfield, Kings County, New Brunswick, Canada in 1788. He left his entire estate, including three enslaved people (likely Jack, Betty, and Sukey), to his wife, Hannah. Hannah remarried and settled with her husband Benjamin Woolsey in Bridgeport, Connecticut; it is not known whether Jack, Betty, and Sukey accompanied Hannah and her new husband. Hannah died in Bridgeport in 1825. There is no reference in her will to any of the three enslaved people although slavery persisted in Connecticut under the gradual emancipation law of 1784 until it was abolished entirely in 1848. (Davidson, "A Violent and Active Tory: The Loyalists of Deerfield".)
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