Nathaniel and his brother Samuel, Jr. jointly owned a farm in 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. The Provincial Government of Massachusetts confiscated and auctioned Nathaniel's Deerfield estate in June 1776 and officially banished him from Massachusetts in 1778. As a result, Nathaniel's enslaved man, Caesar Bailey, became the property of his brother, Samuel, Jr. The Dickinson brothers shared Cato (also known as Dick Cato,) and Caesar's wife Hagar. 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 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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