Where the Annapolis River and the Nictaux river meet was a popular shad fishing spot for Mi'kmaq families before the arrival of the European settlers. It would be later settled by French Acadians that used these waterways to reach the capital of Port-Royal and farming. In the late 1750s the region was settled by New England Planters, and Loyalists to replace the ousted French Acadians. The first four families to be granted land there would later comprise the town of Middleton. They included families with names like Gates and Marshall and Richardson. Col. Philip Richardson received six lots of two hundred and fifty acres each, which ran from the Annapolis River half way to the Mountain to the north, while his neighbour to the west, Anthony Marshall, got two 424-acre lots which ran all the way to the top of the mountain. A Neily family, from Ireland via Ardoise in Hants County, got the next two lots in what would be Lower Middleton, while Benjamin Chesley got the last two lots, next to the town limits.