Windham provided numerous sites for water power, and as early as 1738 a mill was erected at Mallison Falls. Each landowner cleared the river floodplain for cropland and had river access for transportation to the coast until River Road and Old Gray Road ( United States Route 202) were built linking connected farm buildings on high ground adjacent to the floodplain. Early subdivision of land was in strips perpendicular to the Presumpscot River and Pleasant River. Most of the early inhabitants were farmers, who found the soil loamy and easily worked. Portland had refused to surrender these guns to Captain Henry Mowat as he demanded before he burned the town and they were placed aboard the privateer Reprieve in 1776. Windham's 9-pounder cannon and one swivel gun from the stockade blockhouse were loaned to Portland in 1775. Thirteen Windham men are reported as being members of the Continental Army with George Washington's American Revolutionary War winter encampment at Valley Forge. Windham Minutemen marched to Portland in response to the Burning of Falmouth on 18 October 1775 and sixteen men were drafted from the town for the Penobscot Expedition.
New Marblehead Plantation was incorporated on Jas Windham, named for Wymondham in Norfolk, England. The last Indian attack on the town occurred on May 14, 1756. The town's inhabitants took shelter in the stockade between 17. The single gate through the stockade wall was covered by a 4.2-inch (11 cm) bore 9-pounder cannon within the blockhouse. The blockhouse was surrounded by a stockade wall of 12-inch diameter log posts 16 feet long. A 50-foot square blockhouse constructed of 12-inch thick hewn hemlock had an overhanging second story with firing ports and two swivel guns in watch posts on diagonal corners. By order of the Massachusetts General Court, a fort was built in spring of 1744 on a hill in the southern part of town near the early center of settlement to offer protection during King George's War. In 1737, New Marblehead Plantation was settled by Captain Thomas Chute. The township was granted in 1734 by the Massachusetts General Court to Abraham Howard, Joseph Blaney and 58 others from Marblehead, Massachusetts.
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