Nathaniel Dickinson (1734-1788) and his brother Samuel, Jr. 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 for the army until 1783. After the war, he settled in New Brunswick, Canada. The Deerield Committee of Safety and Correspondence confiscated Nathaniel's share of the farm at Mill River in June 1776. 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.” Nathaniel's property was auctioned in 1781 and the proceeds were paid to the state treasury. He was officially banished from Massachusetts in 1778.
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." 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 Brunswisk, 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.
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