From The Story of Dartmouth, by John P. Martin:
Initially there were about 30 men at the Eastern Battery at Imperoyal, but in the autumn of 1755, military records tell us that a considerable number of soldiers spent the winter on this side of the water. These were none other than the troops of Colonel John Winslow, who had just returned from their job of expelling the Acadians.
Winslow’s diary of November 1755 says that “My 54 non-commissioned officers and privates are at Dartmouth”. In the same records is a memo signed by Henry Dobson stating that Lieut. Billings and Ensign Barrel, one Sergeant, one Corporal and all the [Indigenous people] and [Black people] that belong to Colonel Shirley’s regiment are also here at Dartmouth.
Dr. John Thomas, a surgeon in Winslow’s expedition, has a very complete account of life in Dartmouth that winter. Even the weather is noted. On December 12 he wrote: “Snow last night, we paraded 150 men who went over to Dartmouth under the command of Captain Speakman to take up winter quarters there”.
On December 26, Colonel Winslow came over to Dartmouth to review the men posted there, and on the 28th (probably a Sunday), Mr. Phillips preached in Clapham’s windmill. By the end of that month, the roll of troops in Dartmouth totalled 230.
The reference to the windmill at the Canal suggests that these men were quartered in the buildings near there. If so, Mr. and Mrs. Walter Clarke’s tavern on “Front Street” probably did a thriving business with the soldiers, as Murdoch’s History states that the civilian population is small, consisting only of about five families at that time.