Winners and Losers: Part 1–The Captains at Fort George


Throughout the 1600s, war between France and Great Britain that had originated first in Europe or on the high seas spilled over into the American colonies. During these conflicts, allies from various Native tribes aided either the French or British, aligning themselves to best benefit their own needs. Lovewell’s War marked the first international war initiated by Native Americans. This time, the Wabanaki combined tribes had fought the British expressly in response to British encroachment on Wabanaki territory.

Main, Nova Scotia, Iraquois Nation

After Lovewell’s War, “Main” met Nova Scotia at Pemaquid. Note the “Country of the Northern Iroquois in the northwest corner of the map. (Other Maps, July 25, 2017.)

In the end, the French lost ground in Maine, while the British continued to push north and east. The Maine Wabanaki also lost ground, but some Canadian tribes received British recognition of their sovereignty over themselves—at least on paper.

Here in Maine, the Gyles, Woodside, Dunning, Harmon, and Jaques families, after having survived three years of fighting, surely must have considered themselves winners.

Or did they?

Capt. Gyles, in possession of his father’s farm in Topsham, and after a decade commanding Fort George, seemed set for permanent residence in the area. But any soldier, even the commander of a fort, is not in charge of his own life. And sometimes, following orders leads to unexpected consequences.

Near the end of the war, in April 1725, Capt. John Gyles was ordered to take some of his men on a ten-day march along the Androscoggin to search for Native encampments. When he returned from his mission, Gyles learned that Natives had killed two soldiers at the fort.

These may have been Robert and Andrew Dunning, who had been killed by Natives hidden on the Brunswick shore of the Androscoggin, near Mason’s Rock. The Natives shot the brothers as they paddled their canoe from Topsham to Brunswick, instantly killing Robert. Andrew was able to paddle back to the Topsham shore, where he lived only a few minutes more. The brothers were buried together just outside the fort, under one gravestone. We’ll never know for sure the year the brothers died because no date could be seen on the shattered headstone when it was unearthed a century later.

The soldiers who died in April 1725 may have sealed the fate of Capt. Gyles. That December he was replaced by Capt. Woodside of Maquoit and sent northeast to Fort St. George near Thomaston.

Woodside, Wm signature Wheelers'

The new commander, Ulster Scot William Woodside, was the son of Rev. James Woodside. You may recall the Reverend had been hired as Brunswick’s minister in 1718, then dismissed the following year. The Woodside family spent considerable time, effort, and money to build a garrison house at Maquoit. This blockhouse saved their own and their neighbors’ lives during the Native attack in 1722. Unfortunately, the Woodside family and their neighbors lost all their livestock and provisions, leaving them scrambling to resupply their food stores. Brunswick and Topsham residents, as well as those of other frontier towns, lived the next three years in their local garrisons. They left only to tend crops and hunt wild game or fowl, always fully armed and accompanied by their dogs to warn of Natives hiding in the brush.

Woodside Wm payment to Indians

Perhaps in retaliation for those years of deprivation, Capt. Woodside seemed to enjoy getting the best of the Natives. In 1726, when Massachusetts governor William Dummer and Judge Samuel Sewall were at Arrowsic to make a treaty with the Wabanaki, the Natives complained to the officials that Woodside cheated them at his trading post. First, they said, he weighed their furs by placing his fist on the scales instead of using a one-pound weight. Then, they said, Woodside sold them brass beads instead of gold ones, and also watered down their rum. The evidence against him was overwhelming. Woodside was found guilty of the charges and was ordered to admit to the charges, promise not to cheat the Natives again, and to pay them what he owed.

Woodside would find himself in court at least twice more in the ensuing years. In 1732 Samuel Boone accused Woodside of stealing several head of cattle at Chebeague Island and Merriconeag Neck. The court found in favor of Woodside and the cattle were turned over to him. Three decades later, John Orr of Mair Point (Mere Point) sued Woodside for cheating the “Indians ‘by selling them brass rings for gold rings.’” Woodside was acquitted once again.

Still, men like Capt. Woodside helped Brunswick to grow. They held town office, continued to protect against Native attack, farmed wheat and turnips for food, hemp and flax for weaving cloth, and harvested and exported logs and lumber to pay for their land. The town expanded away from the safety of Fort George, to Maquoit and New Meadows. The settlers continued their work on the First Parish Meeting House, which had been interrupted by war, officially completing it in 1735. With the house of worship came a new cemetery and the ancient burying ground at the fort was abandoned.

Over the years, Woodside bought some 350 acres of land in the Wharton Point area; he continued to trade with the Native Americans. Perhaps ironically, about the time he was sued by John Orr, Woodside was commissioned as a Cumberland County justice of the peace.

Wm Woodside Esq tombstone

William Woodside, Esquire, lived to see the beginning of the Revolutionary War. He is buried in the old First Parish Cemetery on upper Maine St.

Meanwhile, Capt. John Gyles continued in service to his country, retiring from Fort St. George in Thomaston in 1728, but continuing to serve the Crown as interpreter of Native languages. In 1736 he wrote about his boyhood experiences as a captive of the Maliseet tribe and the French. His only son, Samuel, completed medical studies in Massachusetts and opened a practice in Salisbury. He married his cousin, Elizabeth True. Their children were both born in Salisbury: John, who died at age two, and a daughter, Hannah. By the late 1730s, when his father had returned to Massachusetts, Dr. Gyles appears to have settled in Brunswick, perhaps taking up his father’s two in Brunswick. If he practiced in town, he would have been the town’s first physician.

Unfortunately, he died Feb. 11, 1738/9, at the young age of 32. His death ended Capt. John Gyles’ direct male line.

DSC03243 (1)

Dr. Gyles is also buried in the First Parish Cemetery. After 280 years, part of his hand-carved tombstone still survives in the graveyard on upper Maine St.

Next Blog: Winners and Losers: Part 2—The Rest of the Story


  •, vital records, family histories, family trees, and databases.
  • Owen, Emanuel. Image A New and Accurate Map of New Jersey, Pensilvania, New York and New England…, London, 1747. Osher Maps Permanent URL: Accessed July 25, 2017.
  • Desmarais, Barbara A., Images of Samuel Gyles and William Woodside, Esq. tombstones. First Parish Cemetery, Upper Maine St., Brunswick, Maine, July 20, 2017.
  • Gyles, John. Introduction by Hannay, James. Nine years a captive, or, John Gyles’ experience among the Malicite Indians, from 1689 to 1698. Saint John, N.B.? : s.n. 1875. Internet Archive. Accessed Sept. 3, 2016.
  • Massachusetts General Court. Acts and resolves passed by the General Court, Vol. Resolves 1726-1733. Boston: Secretary of the Commonwealth. Internet Archive. Accessed July 25, 2017.
  • McKeen, John. Four Lectures on the History of Brunswick. Brunswick, Curtis Memorial Library, 1985. Call No. 974-191.
  • Wheeler, George Augustus Wheeler, MD. And Henry Warren Wheeler. History of Brunswick, Topsham, and Harpswell, Maine. (Wheelers’) Alfred Mudge & Son, Printers, Boston, Mass., 1878., accessed July 30, 2016.
  • Woodside, William signature image. Wheelers’.

(c) Copyright 2017 Barbara A. Desmarais



About Barbara Desmarais

Writer and amateur historian
This entry was posted in Brunswick History and tagged , , , , , , , , . Bookmark the permalink.

6 Responses to Winners and Losers: Part 1–The Captains at Fort George

  1. Julie A. Potter-Dunlop says:

    Good stuff, Barbara!!! Cousin Julie

  2. Thank you, Cousin Julie. Personal stories are my favorites!

  3. Deb Gould says:

    You make much better sense of the early French/British/Indian complications than my history books did when I was in school…where were you then?

  4. Cathy Leonard says:

    Thank you, Barbara! Love to hear the details of my Woodside ancestors lives!

  5. It’s so interesting to know who we come from.

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