In the early decades of the history of Sherbrooke it is often difficult to tell whether events are taking place at Sherbrooke or at some other district on the St. Mary's River. As John McGregor observed in British America "all embryo settlements in America are nothing more than log-houses, in small openings made in the forests, scattered along banks of rivers, roads, or the sea-shore, with occasionally a sawmill, grist mill, smithy, tavern, shop, place of worship, and school house".(13)
The Township Book of St. Mary's Settlement(14) states that the settlement of Saint Mary's River "began in the year 1800 by Robert Taylor, William Taylor and David McKeen and their families" from Truro, Nova Scotia. Robert and William Taylor were sons of Matthew and Elizabeth (Archibald) Taylor, a grantee of Truro township, while David McKeen had come from Connecticut as a boy in 1762 to Truro with his father John McKeen.(15) David was married to Jennet Taylor, a sister of Robert and William, and had eight sons and three daughters, all born in Truro.
David McKeen in a petition to Lieutenant-Governor Sir John Sherbrooke said that in 1798 "then residing in the township of Truro with his family having heard that there were un-granted lands of a good quality on the St. Mary's River, he with several others in company, at their own expense explored the said River and finding a Tract of good land about the forks of said River which they then expected to have been vacant or un-granted, they were at the expense of procuring a survey of the grant to Lyons and other to ascertain the certainty thereof, which cost your petitioner and his said associates upwards of seventy Pounds... the expected Tract of land proved to be within the aforesaid Grant, which your Petitioner and some of his said associates purchased immediately and were the first Settlers upon the said River, and bore all the hardships of settling in so remote a situation without, at that time, any road or communication with any other part of the Province, still in expectation of obtaining Government land adjoining..."(16)
David McKeen declared that he had erected the first Grist mill in the settlement and "has been at considerable expense in maintaining her in the infant settlement". He had two sons still living with him, James McKeen, 21 years old, and Matthew McKeen, 19.
William Taylor declared in his petition that he had shared in the expense of obtaining the survey of the Binney Green Grant, and had been forced to buy the lands they wished to settle upon, and that he had spent upwards of $120 on the erection of a grist mill on St. Mary's River "being the first and only one built on that river... said Mill has since been of great importance to the settlement".
We may wonder why this group from Truro, on the other side of the province, was interested in St. Mary's. The answer probably lies in the names of the Rev. James Lyon and Colonel Alexander McNutt in the Binney grant of 1765, for the Rev. James Lyon (a graduate of the College of New Jersey) had come to Onslow in 1764 as a Presbyterian missionary and was interested in land speculation. In 1772 he had removed to Machias, Maine, where he became a noted patriot during the American Revolution.
Colonel Alexander McNutt, soldier, speculator, land agent and one of the most colourful figures in Nova Scotian history, was instrumental in persuading the Scots-Irish to settle at the townships of Truro, Onslow, Londonderry and New Dublin. Some of the Ulsterman had come directly from Ireland, but the majority came from New Hampshire.(17) Now the Ulster settlers were looking for farms for their younger sons and had already begun to move into the Musquodoboit Valley.
These early settlers to St. Mary's had to drive their cattle nearly forty miles through the woods from either Pictou or Musquodoboit "without a road", and to transport their families and baggage by land to Halifax, and from there by sea up the St. Mary's River to the head of the tide, and from the river to their houses "which had been previously built and well sorted with necessaries for their subsistence".(18) One party found that their dwellings had been burned in their absence. Alexander Manson of St. Mary's, who had emigrated from Scotland, mentions being burned out and being reduced to great poverty.(19)
Robert and William Taylor did not remain long at St. Mary's for in September 1806 Robert and his family removed to the United States and two years later William moved nearer to Halifax, to Chezzetcook.(20) In the meantime two other Taylor brothers, Archibald and John, had come in 1803 and 1805. John's son, Wentworth Taylor (who had been born at Truro March 4th, 1787) was to become the first clerk of the township of St. Mary's and as Justice of the Peace married a number of settlers before there was a settled minister. Wentworth himself travelled to Halifax to marry Esther Fisher of Musquodoboit at St. Matthew's Presbyterian church on the 18th of January 1811. It was the custom of many inhabitants of the Eastern Shore to journey by sea to be married at St. Paul's Church of England or at Matthew's Presbyterian.
David McKeen had been joined in May 1804 by his brother John McKeen 2nd (who was married to Elizabeth, a daughter of Dr. John Harris, a pioneer doctor in Nova Scotia.) Another Truro man, James Whidden (who was married to Jane Fisher, a daughter of James Fisher and Margaret McKeen his wife) settled in St. Mary's in 1804. Timothy McLean, an Irishman who had migrated to America in 1766, settled in St. Mary's in December 1804 with his sons James, John, Daniel and Hugh. The McLean boys had been born at Jordan River in Shelburne County.(21)
James Fisher of Truro (who was married to Margaret, a sister of David McKeen), settled in St. Mary's in 1805 with his sons William, John and David. Born in Londonderry, New Hampshire, James had come to Truro in 1761 with his father William and had lived with his family on the Musquodoboit River for eight years before coming to St. Mary's. By 1809 he had built a sawmill in Truro, a grist mill on the Musquodoboit River and a sawmill at St. Mary's River "all of which have answered the purpose intended with good effect."(22) His sons David and William erected "a sawmill and grist mill at the head of the Tide on St. Mary's River which have answered the purpose intended with good effect though, your petitioner has sustained considerable loss by the former".(23) Probably this was the first mill on the site of the present Sherbrooke.
Angus McDonald, who had been born on the Island of Skye, North Britain, and had undoubtedly served in the British Army in the American Revolution, settled in St. Mary's in 1808. He was married to Martha Fisher, a daughter of James Fisher. Thus the early settlers on the St. Mary's River were closely connected by marriage and blood.