The Penobscot Expedition was a 44-ship American naval armada during the Revolutionary War assembled by the Provincial Congress of the Province of Massachusetts Bay. The flotilla of 19 warships and 25 support vessels sailed from Boston on July 19, 1779, for the upper Penobscot Bay in the District of Maine carrying an expeditionary force of more than 1,000 American colonial marines and militiamen. Also included was a 100-man artillery detachment under the command of Lt. Colonel Paul Revere.
Captain Jeremiah O'Brien (1744–1818) was an Irish-American captain in the Massachusetts State Navy. Prior to its existence, he commanded the sloop Unity when he captured the British armed schooner HMS Margaretta in the Battle of Machias, the first naval battle of the American Revolutionary War. He also led the first American attack on Nova Scotia in the Raid on St. John (1775). Six United States ships were named in his honor.
Samuel Tucker was an officer in the Continental Navy and the United States Navy.
The Battle of Fort Cumberland was an attempt by a small number of militia commanded by Jonathan Eddy to bring the American Revolutionary War to Nova Scotia in late 1776. With minimal logistical support from Massachusetts and four to five hundred volunteer militia and Natives, Eddy attempted to besiege and storm Fort Cumberland in central Nova Scotia in November 1776.
The 84th Regiment of Foot (Royal Highland Emigrants) was a British regiment in the American Revolutionary War that was raised to defend present day Ontario, Quebec and Atlantic Canada from the constant land and sea attacks by American Revolutionaries. The 84th Regiment was also involved in offensive action in the Thirteen Colonies; including North Carolina, South Carolina, Georgia, Virginia and what is now Maine, as well as raids upon Lake Champlain and the Mohawk Valley. The regiment consisted of 2,000 men in twenty companies. The 84th Regiment was raised from Scottish soldiers who had served in the Seven Years' War and stayed in North America. As a result, the 84th Regiment had one of the oldest and most experienced officer corps of any regiment in North America. The Scottish Highland regiments were a key element of the British Army in the American Revolution. The 84th Regiment was clothed, armed and accoutred the same as the Black Watch, with Lieutenant Colonel Allan Maclean commanding the first battalion and Major General John Small of Strathardle commanding the second. The two Battalions operated independently of each other and saw little action together.
The Battle of Machias was an early naval engagement of the American Revolutionary War, also known as the Battle of the Margaretta, fought around the port of Machias, Maine.
The Raid on Lunenburg occurred during the American Revolution when the US privateer, Captain Noah Stoddard of Fairhaven, Massachusetts, and four other privateer vessels attacked the British settlement at Lunenburg, Nova Scotia on July 1, 1782. The raid was the last major privateer attack on a Nova Scotia community during the war.
The Battle of Machias was an amphibious assault on the Massachusetts town of Machias by British forces during the American Revolutionary War. Local militia aided by Indian allies successfully prevented British troops from landing. The raid, led by Commodore Sir George Collier, was executed in an attempt to head off a planned second assault on Fort Cumberland, which had been besieged in November 1776. The British forces landed below Machias, seized a ship, and raided a storehouse.
The Battle off Halifax took place on 28 May 1782 during the American Revolutionary War. It involved the American privateer Jack and the 14-gun Royal Naval brig HMS Observer off Halifax, Nova Scotia. Captain David Ropes commanded Jack, and Lieutenant John Crymes commanded Observer. The battle was "a long and severe engagement" in which Captain David Ropes was killed.
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 Saint John River in June 1777.
The Battle of Blomidon took place on 21 May 1781 during the American Revolutionary War. The naval battle involved three armed U.S. privateer vessels against three Nova Scotian vessels off Cape Split, Nova Scotia. American Privateers caught two Nova Scotia Vessels. The first Nova Scotia vessel was re-captured by Lieut Benjamin Belcher. The second Nova Scotia vessel was overtaken by the captured crew under the command of Captain Bishop. The privateers were taken to Cornwallis and put on trial.
The Raid on Annapolis Royal took place on 29 August 1781 during the American Revolutionary War. The raid involved two American privateers - the Resolution and the Reprisal - attacking and pillaging Annapolis Royal, Nova Scotia in revenge of the defeat of the Penobscot Expedition. The privateers took captive the commander of the militia John Ritchie, described as the "Governor of Annapolis." One historian described it as "one of the most daring and dramatic raids upon Nova Scotia."
The Raid on Charlottetown of 17–18 November 1775, early in the American Revolutionary War, involved two American privateers of the Marblehead Regiment attacking and pillaging Charlottetown, Prince Edward Island, then known as St. John's Island. The raid motivated Nova Scotia Governor Francis Legge to declare martial law. Despite the raid's success, George Washington immediately freed senior colonial officials the privateers had brought back as prisoners to Cambridge, Massachusetts.
The Battle off Liverpool took place on 24 April 1778 during the American Revolutionary War. The raid involved the British vessel HMS Blonde and the French 24-gun frigate Duc de Choiseul.
The Raid on Yarmouth took place on 5 December 1775 during the American Revolutionary War. The raid involved American Privateers from Salem, Massachusetts attacking Yarmouth, Nova Scotia at Cape Forchu. The privateers intended to stop the export of supplies being sent from Nova Scotia to the loyalists in Boston.
The Battle off Yarmouth took place on 28 March 1777 during the American Revolutionary War off the coast of Yarmouth, Nova Scotia. The battle is the first American armed vessel to engage the British Navy. The British vessel HMS Milford forced the American USS Cabot aground and the American crew escaped among the inhabitants of Yarmouth.
The Province of Nova Scotia was heavily involved in the American Revolutionary War (1776–1783). At that time, Nova Scotia also included present-day New Brunswick until that colony was created in 1784. The Revolution had a significant impact on shaping Nova Scotia, "almost the 14th American Colony". At the beginning, there was ambivalence in Nova Scotia over whether the colony should join the Americans in the war against Britain. Largely as a result of American privateer raids on Nova Scotia villages, as the war continued, the population of Nova Scotia solidified their support for the British. Nova Scotians were also influenced to remain loyal to Britain by the presence of British military units, judicial prosecution by the Nova Scotia Governors and the efforts of Reverend Henry Alline.
The American frigate USS Hancock was captured by the British Royal Navy in a 1777 naval battle during the American Revolutionary War. The two highest ranking naval officers of the war battled each other off the coast of Nova Scotia. HMS Rainbow, under the command of British Admiral George Collier, captured USS Hancock, under the command of Captain John Manley.
The Raid on Chester occurred during the American Revolution when the US privateer, Captain Noah Stoddard of Fairhaven, Massachusetts, and four other privateer vessels attacked the British settlement at Chester, Nova Scotia on 30 June 1782. The town was defended by Captain Jonathan Prescott and Captain Jacob Millett.
Captain Stephen Smith was a privateer and militia leader from Machias, Maine who fought in the Raid on St. John (1775). The following year Smith was appointed truck master to the Native Americans to ensure their support during the American Revolution. He also participated in the Battle of Machias (1777). Stephen Smith, after the revolution was appointed by President George Washington under Treasury Secretary Alexander Hamilton in Machias as a Tax Collector. Jim Lawrence Finnie CEO Fantast Corporation is a descendant of Stephen Smith.
Kingdom of Great Britain 
Jeremiah O'Brien [1] [2] Stephen Smith (privateer) [3] [4] 
Captain Frederick Sterling