The project of settling the shores of Port Roseway had its birth in the autumn of 1782, when one hundred and twenty Loyalist families, whose attention had been directed to that part of Nova Scotia by a friend in Massachusetts, banded together with the object of emigrating thither.  They first appointed a committee of seven to make arrangements for their removal; and, a few weeks later, they commissioned two members of the association, Joseph Pynchon and James Dole, to go to Halifax and lay before Governor Parr their desires and intentions.  Pynchon and Dole, on their arrival at Halifax, had an interview with the governor, and obtained from him very satisfactory arrangements.  The governor agreed to give the settlers the land about Port Roseway which they desired.  He promised them that surveyors should be sent to lay out the grants, that carpenters and a supply of 400,000 feet of lumber should be furnished for building their houses, that for the first year at least the settlers should receive army rations, and that they should be free for ever from impressment in the British Navy.  All these promises were made on the distinct understanding that they should interfere in no way with the claims of the Loyalists on the British government for compensation for losses sustained in the war.  Elated by the reception they had received from the governor, the agents wrote home enthusiastic accounts of the prospects of the venture.  Pynchon even hinted that the new town would supersede Halifax.  ‘Much talk is here,’ he wrote, ’of capital of Province...  Halifax can’t but be sensible that Port Roseway, if properly attended to in encouraging settlers of every denomination, will have much the advantage of all supplies from the Bay of Fundy and westward.  What the consequence will be time only will reveal.’  Many persons at Halifax, wrote Pynchon, prophesied that the new settlement would dwindle, and recommended the shore of the Bay of Fundy or the banks of the river St John in preference to Port Roseway; but Pynchon attributed their fears to jealousy.  A few years’ experience must have convinced him that his suspicions were ill-founded.

The first instalment of settlers, about four thousand in number, arrived in May 1783.  They found nothing but the virgin wilderness confronting them.  But they set to work with a will to clear the land and build their houses.  ‘As soon as we had set up a kind of tent,’ wrote the Rev. Jonathan Beecher in his Journal, ’we knelt down, my wife and I and my two boys, and kissed the dear ground and thanked God that the flag of England floated there, and resolved that we would work with the rest to become again prosperous and happy.’  By July 11 the work of clearing had been so far advanced that it became possible to allot the lands.  The town had been laid out in five long parallel streets, with other streets crossing them at right angles.  Each associate was given a town lot fronting on one of these streets, as well as a water lot facing the harbour, and a fifty-acre farm in the surrounding country.  With the aid of the government artisans, the wooden houses were rapidly run up; and in a couple of months a town sprang up where before had been the forest and some fishermen’s huts.