He received a militia captain's commission in 1758, when he apparently saw no action, and again in 1759, when his company was garrisoned at Fort Cumberland (the name Fort Beauséjour was given after its capture).
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He led a failed attempt to capture Fort Cumberland in 1776 and was forced to retreat to Massachusetts, the place of his birth.
In 1755, the British were successful in laying siege to Fort Beauséjour, and with war having officially broken out, Governor Charles Lawrence sent Wilmot, then a lieutenant-colonel, up to Fort Cumberland (Beauséjour's new name), to act as its commander.
:Recommend me kindly to our good friend Monacatootha, and others; tell them how happy it would make Conocotarious to have an opportunity of taking them by the hand at Fort Cumberland, and how glad he would be to treat them as brothers of our Great King beyond the waters.
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On October 1, 1755, while returning to her home from the Fort Cumberland Trading Post several miles away, Jane was captured by Indians and taken to the Miami River in Ohio.
Allan's work was made more difficult by the arrival of Colonel Goreham and his troops to refortify Fort Cumberland, and by the activities of Michael Francklin, a former Lieutenant Governor of Nova Scotia and a vocal Loyalist.
During Bay of Fundy Campaign (1755), on August 28, Monckton sent Major Joseph Frye with an expedition of 200 provincial militia from Fort Cumberland in two armed sloops, with instructions to clear Acadians settlements on the Petitcodiac River.
In the summer of 1776, Mariot Arbuthnot, the new governor of Nova Scotia, ordered Colonel Joseph Goreham's Royal Fencible Americans to secure Fort Cumberland and keep watch for any signs of an American invasion of the province.