"Capt. James Littlefield had several slaves: Scipio, Sharper, Dinah and Tom. Tom married Phillis, but soon after died. She then married Prime. Prime died. She then took Old Tom." - Bourne, p. 409

Note: Capt James Littlefield is said to have enslaved four individuals (Scipio, Sharper, Dinah and Tom) with the same names as four of the six people enslaved earlier by Joseph Hill. The assumption made here is that these were the same people. In the list of "African Americans mentioned by Bourne and Remich" at the BSM exhibit on the Ridge Community, Town Historian Kathy Ostrander Roberts also listed those individuals as having been enslaved by both Joseph Hill and Capt James Littlefield.

"Captain James Littlefield, son of Dependence Littlefield, gained prominence as a soldier of the French and Indian wars, and in 1744 was one of the Wells company enlisted under Colonel John Storer and embarked on board transports for the expedition against Louisburg. He was afterward advanced to the rank of captain and gave valiant service in later years. He was a man of substance, and the records showed that he owned several slaves named Scipio, Sharper, Dinah and Tom. In 1766 he was one of a committee to build a new meeting house, and when the pews were assigned he was mentioned as one of the persons who 'ought to be of the first rank for pews on the floor.'" - Genealogical and Personal Memoirs Relating to the Families of Boston and Eastern Massachusetts, Volume 4, p. 1845

A WikiTree page (https://www.wikitree.com/wiki/Littlefield-688) states that James Littlefield lived abt 1706-Nov. 25, 1780, and was the husband of Lydia Littlefield, having married in Wells in 1723. It provides this cautionary note: "Both James Littlefield [1706] and son James Littlefield [1748] were called Captain James Littlefield." However, the son was born in 1724 and died in battle at Cape Breton in 1745. So, considering the 1776 date of the marriage of his "servants," it is clearly the elder Capt. James Littlefield who was the enslaver of Scipio and the others. Note that "James was in the Louisburg Expedition as was his son James, Jr." So, father and son may have been in battle together in 1745 when James Jr lost his life.

Tom and Phillis who lived on [Negro] Ridge were "Negro servants" of Capt. James Littlefield, and married in 1776. - Remich, p. 108, footnote

Bibliography:

The History of Wells and Kennebunk from the Earliest Settlement to the Year 1820 - by Edward Bourne (1875)

History of Kennebunk from its Earliest Settlement to 1890 - by Daniel Remich

Vital Records of the Town of Wells

Genealogical and Personal Memoirs Relating to the Families of Boston and Eastern Massachusetts, Volume 4 edited by William Richard Cutter, which can be viewed in Google books at: https://www.google.com/books/edition/Genealogical_and_Personal_Memoirs_Relati/H89DXKVm4qcC?q=%22captain+James+Littlefield%22,%22Wells+Maine%22&gbpv=1#f=false