Battle of Fort Loyal The Battle of Fort Loyal ( May 20 , 1690 ) involved Joseph - François Hertel de la Fresnière and Baron de St Castin leading troops as well as the Wabanaki Confederacy ( Mi ' kmaq and Maliseet from Fort Meductic ) in New Brunswick to capture and destroy an English settlement on the Falmouth neck ( site of present - day Portland , Maine ) , then part of the Massachusetts Bay Colony . The commander of the fort was Captain Sylvanus Davis . After two days of siege , the settlement ' s fort , called Fort Loyal ( sometimes spelled " Loyall " ) , surrendered . The community ' s buildings were burned , including the wooden stockade fort , and its people were either killed or taken prisoner . With the fall of Fort Loyal ( Casco ) , led to the near depopulation of Maine . Native forces were then able to attack New Hampshire frontier without reprisal . Historical context . The earliest garrison at Falmouth was Fort Loyal ( 1678 ) in what was then the center of town , the foot of India Street . During King William ' s War , on Major Benjamin Church ' s first expedition into Acadia , on September 21 , 1689 , he and 250 troops defended a group of English settlers trying to establish themselves at Falmouth , Maine ( present - day Portland , Maine ) . Natives killed 21 of his men , however , he was successful and the natives retreated . Church then returned to Boston leaving the small group of English settlers unprotected . Hertel was chosen by Governor Frontenac to lead an expedition in 1690 that successfully raided Salmon Falls on the Maine - New Hampshire border , and then moved on to destroy Fort Loyal on Falmouth Neck ( site of present - day Portland , Maine ) Battle . In May 1690 , four hundred to five hundred French and Indian troops under the command of Joseph - François Hertel de la Fresnière and Baron de St Castin , attacked the settlement . Grossly outnumbered , the settlers held out for four days before surrendering . Eventually two hundred were murdered and left in a large heap a few paces from what is now the popular Benkay sushi restaurant . When a fresh Indian war broke out in 1716 , authorities decided to demolish the fort and evacuate the city rather than risk another catastrophe . Afterward . When Church returned to the village later that summer , he buried the dead . James Alexander was taken captive along with 100 other prisoners . Alexander was taken back to the Maliseet headquarters on the Saint John River at Meductic , New Brunswick . " James Alexander , a Jersey man , " was , with John Gyles , tortured at an Indian village on the St . John river . Two families of Mi ' kmaq people , who had lost friends by some English fishermen , came these many miles to avenge themselves on the captives . They were reported to have yelled and danced around their victims ; tossed and threw them ; held them by the hair and beat them - sometimes with an axe - and did this all day , compelling them also to dance and sing , until at night they were thrown out exhausted . Alexander , after a second torture , ran to the woods , but hunger drove him back to his tormentors . His fate is unknown . Captain Davis spent four months as a prisoner in Canada . Both Falmouth and Arrowsic remained uninhabited until 1714 and 1716 respectively . Endnotes