Battle of Longue - Pointe The Battle of Longue - Pointe was an attempt by Ethan Allen and a small force of American and Quebec militia to capture Montreal from British forces on September 25 , 1775 , early in the American Revolutionary War . Allen , who had been instructed only to raise militia forces among the local inhabitants , had long had thoughts of taking the lightly defended city . When he reached the southern shore of the St . Lawrence River with about 110 men , he seized the opportunity to try . Major John Brown , who Allen claimed was supposed to provide additional forces , did not appear as they had planned , isolating Allen and his men on the north side of the river . British General Guy Carleton sent a force composed mostly of Quebec militia in response to news of Allen ' s crossing of the St . Lawrence . This force cut off Allen ' s escape route , and eventually surrounded and captured Allen and a number of his men . Carleton eventually abandoned Montreal , which fell without battle to Continental Army forces on November 13 . Allen was sent first to England and then New York City as a prisoner , and was eventually exchanged in 1778 . Background . In the 18th century , the city of Montreal occupied only a small portion of the island of Montreal , centered on what is now called Old Montreal . The eastern tip of the island was called " Longue - Pointe " , and there was at one time a fortification called Fort Longue Pointe on the island , across the river from Longueuil . This area , annexed to Montreal in 1910 , and now the Mercier - Est neighborhood of Mercier - Hochelaga - Maisonneuve , a borough of the city , is near where the action described here took place . With the American Revolutionary War beginning , many thought it would be easy to spread the rebellion to the Province of Quebec , which had only been conquered by the British in 1759 , and whose population was seen as resentful of British rule . The American invasion of Quebec began with the arrival at Île aux Noix of the Continental Army under the command of General Philip Schuyler on September 4 , 1775 . Schuyler , who was ill at the time , eventually turned command of the army over the General Richard Montgomery , who ordered the army to besiege Fort Saint - Jean , which they did on September 18 . At this fort , south of Montreal on the Richelieu River , General Guy Carleton had concentrated the few British regulars at his disposal following the capture of Fort Ticonderoga in May . American situation . Before turning command over to Montgomery , Schuyler drafted a proclamation addressed to the people of Quebec , encouraging them to oppose the British and assist the American cause . On September 8 Ethan Allen and Major John Brown went into the countryside between Saint - Jean and Montreal with a small detachment of Americans to circulate this proclamation , meeting with James Livingston , a Patriot sympathizer at Chambly as well as with the local Caughnawaga Mohawk . Livingston eventually raised about 300 local militia , which he encamped at Pointe - Olivier , below Fort Chambly . Allen and Brown returned to Île aux Noix following this tour . Allen had long harboured the goal of taking Montreal . After he and Benedict Arnold captured Fort Ticonderoga in May 1775 , he had taken a few hundred men north from Ticonderoga to Saint - Jean with the idea of capturing the fort there by surprise , and then taking Montreal . This effort was frustrated by the timely arrival of British troops at Saint - Jean ; the exploit made Allen a well - known figure in Montreal and the Richelieu valley . Montreal situation . Following the capture of Fort Ticonderoga in May 1775 , General Carleton , with only 800 regular troops available to defend the entire province , had concentrated those troops at Fort Saint - Jean , placing about 500 troops , along with about 250 militia and natives , at the fort . The remaining forces were distributed among the frontier forts along the Great Lakes , with relatively small garrisons at Montreal , Trois - Rivières , and Quebec City . During the summer of 1775 he attempted to raise substantial additional militia forces from the population . These attempts met with limited success , in part because of successful American propaganda and agitation by Patriot sympathizers , especially Thomas Walker , James Price , and James Livingston . By July , Carleton was apparently satisfied with the level of militia support near Montreal , but he did little to stop the activities of the agitators , who also sent reports detailing British military preparations to the Americans . Prelude . When Montgomery finally began the siege of Fort Saint - Jean , he ordered Allen and about 30 Americans to join with Livingston ' s Canadians to secure the south bank of the St . Lawrence River against attempts by Carleton in Montreal to relieve the siege . He also ordered a larger force under Brown ' s command to secure the area north of the fort , and to cover the road between Saint - Jean and Montreal . Allen traveled along the southeastern banks of the Richelieu River , up to Sorel , where he crossed that river and continued up the southern shore of the St . Lawrence to Longueuil . According to Allen ' s account , he met Brown there , and the two of them then hatched a plan to attack Montreal . Brown would cross the river with 200 men at La Prairie , upriver from Montreal , and Allen , with his Americans and 80 Canadians under the command of Loiseau and Duggan , two of Livingston ' s captains , would cross the river at Longueuil , below the city , and the two forces would , after a prearranged signal , converge on the city itself . Action . Allen and his men crossed the St . Lawrence on the night of the 24th , landing at Longue - Pointe . The inhabitants he met there were friendly , but he posted guards on the road to Montreal to prevent news of their crossing from reaching the city . However , one man they detained managed to escape to the city and inform Carleton of Allen ' s presence on the island . Brown did not cross the river . While no sources indicate why Brown failed to act , historian Justin Smith suggests that Allen in fact acted alone , and only later sought to blame Brown for the endeavour ' s failure . This left Allen ' s force alone and vulnerable , as it had taken three round trips with the available boats to ferry his men across the river . Realizing he would not be able ferry everyone back across the river before troops arrived from the city , Allen chose a wooded area near the Ruisseau - des - Sœurs ( labelled on the map above as " Ruisseau de la G Prairie " ) , between Longue - Pointe and Montreal , to make a stand . He also sent word to Thomas Walker , a British merchant and known Patriot sympathizer with a house in nearby L ' Assomption , for assistance . Walker was able to muster some men , but Allen was captured before they could lend any assistance . When General Carleton received word that the notorious Ethan Allen was at the gates of the city , he raised the alarm . As the news spread , large numbers of people turned out . Captain John Campbell assembled a force of 34 regulars from the 26th Foot ( the entire garrison in Montreal ) , 120 Canadien and 80 English militia , 20 British Indian agents , and a few Indians , and led them out to face Allen ' s force . As Campbell ' s force approached , Allen instructed 10 Canadians to cover his left flank , while Duggan and another 50 Canadians were placed on the right flank . Both of these detachments fled instead of holding their positions , leaving Allen with about 50 men . Over the course of the next 90 minutes , fire was exchanged between the forces . Allen ' s remaining forces were eventually broken , and , after trying to outrun the enemy , he surrendered . Aftermath . The abortive attack on Montreal led to the full mobilization of local militia in Montreal , raising nearly 1 , 000 men , but they soon began to drift away . Carleton refused to organize an expedition in relief of Fort Saint - Jean , and the militia members from rural parishes eventually disbanded to attend to their harvests and the defense of their own homes . In November , the besieged fort ' s commander capitulated , opening the Americans ' way to Montreal . Carleton fled the city , making his way to Quebec City , and Montgomery occupied Montreal without firing a shot on November 13 . Allen and the other captives were brought to the city . Allen , in his account of the encounter , claims that Colonel Richard Prescott was intent on killing the captured Canadien s , but Allen interceded on their behalf , saying " I am the sole cause of their taking up arms . " Allen was imprisoned in a ship ' s hold , and eventually sent to England . He spent about a year , mostly on prison ships , before he was released on parole in British - occupied New York City in November 1776 , as the British authorities feared hanging him would create a martyr . He was eventually exchanged in May 1778 for Archibald Campbell , a British officer , and resumed military and political service for the nascent Republic of Vermont in 1778 . Thomas Walker , the merchant to whom Allen had applied for assistance , was arrested in early October 1775 when twenty regulars and a dozen militia came from Montreal to his house in L ' Assomption . Walker ' s house was destroyed , and he was imprisoned with the intent of sending him to England for trial . Walker was eventually freed when the Americans captured Montreal and most of the British fleet trying to escape the city . Legacy . Ethan Allen wrote a memoir recounting his version of the circumstances of his capture , and the time of his imprisonment . This work , along with Allen ' s other memoirs , were quite popular in the 19th century , going through numerous printings . A city park in the Montreal borough of Mercier - Hochelaga - Maisonneuve , where the action took place , is called " Parc de la Capture - d ' Ethan - Allen " .