St . John River expedition The St . John River expedition was an attempt by a small number of militia commanded by John Allan to bring the American Revolutionary War to Nova Scotia in late 1777 . With minimal logistical support from Massachusetts and approximately 100 volunteer militia and Natives , Allan ' s forces occupied the small settlement at the mouth of the St . John River ( present - day Saint John , New Brunswick , then part of Sunbury County , Nova Scotia ) in June 1777 . The settlement ' s defense was weakened by the war effort and that Americans quickly occupied it and took prisoner British sympathizers . Almost a month later , under command of Brigade Major Studholme and Colonel Francklin , British forces successfully drove off the occupying Americans , forcing Allan to make a difficult overland journey back to Machias , Maine . Allan ' s incursion was the last significant American land - based assault on Nova Scotia during the war , which remained Loyal throughout the war . Historical context . In 1775 , when the American Revolutionary War began , there was a small British settlement at the mouth of the St . John River , where the modern city of Saint John , New Brunswick is located . The territory was at the time part of Nova Scotia , and was defended by a small garrison stationed at Fort Frederick . When the war broke out , the garrison was withdrawn to Boston . Under the command of Stephen Smith , an American militia from Machias , Massachusetts ( now part of Maine ) immediately attacked and burned Fort Frederick . In late 1776 , Jonathan Eddy raised a mixed force of Indians , Massachusetts Patriots , and Nova Scotian sympathizers , and unsuccessfully besieged Fort Cumberland , which protected the land approach to Halifax from the west . Privateers also became active in raiding both Nova Scotia shipping and its communities . By the end of 1776 , the Americans had taken nearly 350 prizes and raided the Nova Scotian communities of Yarmouth , Digby , and Cornwallis . In early 1777 John Allan , an expatriate Nova Scotian , was authorized by the Second Continental Congress to organize an expedition to establish a Patriot presence in the western part of Nova Scotia ( present - day New Brunswick ) . Although Congress authorized him to recruit as many as 3 , 000 men , the Massachusetts government was only prepared to give him a colonel ' s commission and authority to raise a regiment in eastern Massachusetts to establish a presence in the St . John River valley . Allan ' s intention was to establish a permanent post in the area and to recruit the local Maliseet and European settlers to join the American cause . He hoped to recruit a large enough force to launch another assault on Fort Cumberland . Expedition . Colonel Allan left Machias with a party in four whale boats and four birch canoes , on May 30 , 1777 . The party , including Indians , numbered 43 men . More than half of Allan ' s troops had served under Eddy at Fort Cumberland . By the morning of June 2 , reinforced by 13 canoes , Allan had proceeded eastward along the coast to Mechogonish ( Duck Cove ) , west of the mouth of the St . John . Having ascertained that there were no ships or garrison at the mouth of the St . John , Allan dispatched a party of 16 men under Captain West , who marched through the woods , crossed the river above the Reversing Falls in bark canoes , and made their way to Portland Point , where they surprised and captured James Simonds and William Hazen , two of the St . John settlement ' s founders and leading businessmen . Col . Allan and his party remained about a month on the St . John recruiting Maliseet Indians . Whilst engaged in his negotiations , which primarily took place at the Maliseet encampment known as Aukpaque ( just upriver from present - day Fredericton , New Brunswick ) , Allan had posted nearly all his men , some 60 in number , at the mouth of the St . John , under command of Captains Dyer and West . Allan ' s intention of establishing a permanent post was cut short when British authorities in Halifax learned of his operation from a Loyalist who escaped Allan ' s men . The Lieutenant Governor of Nova Scotia , Admiral Marriott Arbuthnot , sent several British war vessels to the mouth of the river . On Monday , June 23 , under command of Brigade Major Gilfred Studholme and Colonel Michael Francklin , the British sloop - of - war HMS " Vulture " arrived , and a few days later she was joined by the frigates " Milford " and " Ambuscade " , with a strong detachment of the Royal Fencible Americans and the 84th Regiment of Foot ( Royal Highland Emigrants ) on board . On the morning of June 30 , about 120 men left the ships in barges . They landed at Mahogany Bay ( now known as Manawagonish Cove , southwest of Saint John ) and then marched in the direction of the falls , and had a brief skirmish with Allan ' s men in the vicinity of the present village of Fairville . In the short firefight , twelve Americans and one member of the 84th regiment were killed . The Americans quickly retreated up the river . Dyer , West , and Allan returned to Machias by way of the Oromocto and Magaguadavic rivers . Aftermath . Col . Allan ' s untiring efforts to gain the friendship and support of the Indians , during the four weeks he had been at Aukpaque was somewhat successful . There was a significant exodus of Maliseet from the region to join the American forces at Machias . On Sunday , July 13 , 1777 , a party of between 400 and 500 men , women , and children , embarked in 128 canoes from the Old Fort Meduetic ( 8 miles below Woodstock ) for Machias . The party arrived at a very opportune moment for the Americans , and afforded material assistance in the defence of that post during the attack made by Sir George Collier on the 13th to 15 August . The British did only minimal damage to the place , and the services of the Indians on the occasion earned for them the thanks of the council of Massachusetts . After Allan ' s expedition the British settlers on the St . John demanded a better defense from Halifax . In response , Major Studholme was sent to provide a permanent military presence ( fortuitously frustrating plans by raiders from Machias to further plunder the St . John settlement ) , and Fort Howe was built under his auspices in late 1777 . The fort protected Saint John for the rest of the war , and the area became a major settlement for expatriate Loyalists after the war . William Hazen and his associates were influential in efforts to retain the loyalty of area Indians to the British cause . Nova Scotia was not subjected again to land - based invasions , but there continued to be raiding by privateer s throughout the war . Later raids on Nova Scotia happened at Liverpool and Lunenburg . Naval battles also took place off the coast of Nova Scotia , including a battle off Halifax and another off present - day Sydney .