The TOWN of RAYMOND, as we know it here and now, had its start with the arrival of its first two settlers in 1770. But its story would start a century earlier when William Raymond, or Rayment as it was then sometimes spelled, of Beverly, Massachusetts, earned public recognition by leadership participation in the 1675 militia attack on the Rhode Island Indian stronghold of Narragansett in the Great Swamp Fight in King Phillips War. Then when the resentful Indians allied themselves with the French adventurers in Quebec to harass the English settlements along the Atlantic coast, Captain William Raymond raised a company of 60 men of Beverly to participate with some 2500 other Massachusetts colonists under Sir William Phipps in an attempt to destroy the French fortress, the center of French activity in the new world. They did attack and enter the city but the arrival of winter and epidemic in the fleet resulted in disaster and great loss of life.
Massachusetts had no money for payment of their services and the promise of gain through captured loot was not realized, leaving the survivors and dependents without compensation until 1735 when a move was made to reward them with grants of land. Townships of land were taken by these companies of soldiers as settlement. Town facilities and roads were laid out and individual land parcels drawn by lot. Called "Canada Towns" due to their origin to differentiate them from other types of land grants, the Beverly Company township was called "Canada #1" or "Beverly-Canada". Some three dozen other similar companies from seacoast towns north and south of Boston formed a semi-circle of settlements 50 to 100 miles further inland, intended to act as a defensive barrier to discourage further French and Indian depredations.
In 1741 another continuing problem, that between Captain John Mason who, together with Sir Ferdinando Gorges had been granted the "Province of Main" in 1622 and claimed the land north of the Merrimac River, was terminated. With now an acknowledged boundary between Massachusetts and Mason's province of New Hampshire, Beverly-Canada was found to be in the new Province along with many other invalidated Massachusetts grants. Attempts to come to terms with the New Hampshire Proprietors were unsuccessful and the illegal squatters could only go back to Beverly and other towns and forfeit their rights and hard work. Eventually what had been Beverly-Canada became the present town of Weare, west of Concord, and Manchester, New Hampshire.
By 1760 another attempt was initiated to compensate the deprived "Canada Soldiers", by now all heirs or assigns of the original veterans, with grants of land in the Province of Maine which belonged to Massachusetts by acquisition from the Gorges heirs. Permitted in 1765 to select from unappropriated land adjacent to a settled town, the Beverly Proprietors, still led by descendants of William Raymond, considered sites and visited one up the Royal River above North Yarmouth but finally selected our present location next to the settled town of Windham in 1767. Many of the other Canada Towns similarly evicted from New Hampshire were doing the same, such as Rowley-Canada (Bridgeton), Newbury-Canada (Poland), Gorham- Canada of Barnstable (Otisfield), Whitman-Canada (Waterford), Newton-Canada (Paris), and Sudbury-Canada (Bethel).
Cumberland County had been formed in 1760 from a part of York County and the land, except for the townships established in 1735 at the time and manner of the Canada Towns, was virginal wilderness. A surveyor, George Peirce of Otisfield, was engaged to survey and lot out the town of Raymond for settlement. The Beverly Proprietors drew for their lots again, in four divisions of 64 shares (60 for the company, one for the first settled minister, one for the support of the ministry, one for the support of schools, and one for Harvard College) in accordance with the terms of the grant. Taxes or assessments were paid to Massachusetts through the tax collector of Windham and prospective settlers acquired their 100 acre parcels directly from the individual proprietors.
The first arrival of settlers was in 1770 when Joseph Dingley and Dominicus Jordan of Cape Elizabeth came up the Presumpscot River to Sebago Pond, attracted by the proprietors' offer of a free 100 acre lot to the first claimants on the spot. Resting overnight at the foot of the lake, Dingley stole away early with their canoe to the first (at the head of Kettle Cove) leaving Jordan to walk the shore to the mouth of the Jordan River where he set his stake in second place. Arrivals continued with early names of Cash, Davis, Brown, Gay, Staples, Leach, Tinney, Crisp, Smith, Simonds, and others. Log cabins were erected, land was cleared by massive cutting and burning of forests and means of subsistence and livelihood were established.
In the first rush of settlers to provide shelter on a productive site, assigned lots according to the Peirce survey map were difficult to discover and more ignored than observed. By 1790 tenancy and lines were in a mess, unsolvable by Peirce or the proprietors. Jordan and Dingley were directed by the proprietors to get a new survey, discovering the Peirce lines if possible, and present the plan by 17 March 1791 or forfeit their pay. This they did on that date, with Nathan Winslow of Portland as surveyor, though they failed to note on each lot the nature of the land as directed due to the work being done with snow on the ground. Lines were not cleared for sightings or elevations and generous allowances were made for "swag of chain" so that most 100 acre lots were, and still are in excess of that size. Many adjustments and changes in both map and sites were necessary before the first deeds could be written and recorded on 29 March 1794, but at last there was some order and legitimacy to the township of Raymondtown, Massachusetts.
With the inadequacies in a proprietary form of government in a growing settlement, Raymond became the 146th incorporated town in the District of Maine, Commonwealth of Massachusetts, on 21 June 1803. Town offices were established to afford self government, but Boston was a long way off and indifferent to the needs of the people. Given this situation, together with the interposition of the State of New Hampshire between the Commonwealth and District, it was not long before there was agitation for Maine statehood, which came in 1820. Growth had been rapid and continuous as settlers arrived and families grew, prospering through agriculture and timber for Portland and other seacoast towns running short of natures bounty.
Raymond was difficult to administer, since it was one of the largest townships in Maine by virtue of the original land request in 1765 being enlarged to offset the large area taken by lakes and ponds that were then of little agricultural use. But in 1829 the town was reduced in area by the taking of that part of Raymond to the west and north of Crooked River which, together with portions of Otisfield, Harrison, Bridgton, and Sebago formed the new town of Naples. Then with the wilderness of Rattlesnake Mountain in the center of town, there was dissatisfaction by those living in the western part due to their insulation from and the greater attention given the eastern part where Town Meetings were held in Raymond Village. In 1838, by petition to the legislature, the western part tried to become a separate town but did not succeed. In 1841 a second try was successful and on March 18, 1841 a new town was named Casco, reducing Raymond to about half in area and population. There were, however gains when, in 1859, a gore of land between Raymond and Gray and another between Raymond and Standish Cape were annexed to Raymond followed by, in 1869, the annexation of Standish Cape itself.
Steady growth and activity in the area continued to a peak in 1860, terminated by a combination of effects of the Civil War followed by the post-war movement of people and business to the newly opened west. Maine, noted for its large families engaged in agriculture, had a greater percentage of its population in the military service than any other state during the war and after that conflict, the western style of farming and free land, together with movements of the labor force to the industrial cities for mill occupations, created a precipitous decline in population equal to the climb before the Civil War. This reached its nadir in 1930, since which time it has resumed its earlier rapid increase and had passed its 1860 peak by 1970 with no indication yet of any tapering off.