Captain John MacGregor, (1759-1823) son of James of Glengyle, grandson of Gregor "Ghlun Dhu", descendent of Clan Gregor Chiefs; was baptized as "John Grahame" due to the proscriptions renewed in 1693 against the Clan Gregor.  John emigrated to the thirteen colonies in 1774 with his father and several siblings, under the tragic "clearances" (depopulation of the highlands), instantly reverting to "John MacGregor", as soon as he got off the ship in Philadelphia.

At the outbreak of the American Revolution, he was a volunteer in the Loyal Philadelphia Volunteers. He refused a Captaincy in the American Revolutionary Army, but soon transferred to the Loyal New York Volunteers as an ensign. He fought for eight years under the command of Col. George Turnbull in the areas of Long Island, Savannah and Charleston, Ga., and Lancaster, Pa.

His father died as a Loyalist soldier in the war.  He was promoted to the rank of Lieutenant, and returned to Long Island in 1783.  After the "Treaty of Separation", he went to Shelburne, Nova Scotia, with three of his brothers, where he was awarded a city lot.  He married Mary MacMillan there and started a family which eventually would number 13 surviving children.

In 1784, New Brunswick was declared a separate Crown colony, so John and 14,000 other Loyalists including 14 remnants of British American regiments, arrived in the wilderness of Nashwaak, NB.  These soldier/settlers formed a militia that was expected to defend the new colony against probable American encroachment.  John joined the Regular 42nd Highland Regiment (Black Watch) and maintained his military connections throughout those inter-war years.

After many early hardships, he prospered there.  In 1791, Upper Canada was declared a separate Crown Colony and later, in 1806,  when vast tracts of land around the Sandwich area (later Windsor) were opened up, he decided to take his family there, where he was awarded 200 acres of forested land.  He transferred from the 42nd to the Kent Riflemen Militia Unit.  Sgt. MacGregor was so impressed with Gen. Sir Isaac Brock that he named his next son. born in 1809,  after him.

In early 1812, when the second war against the U.S. erupted, a sizeable army marched north from Kentucky towards Ontario.  When General Sir Isaac Brock, took Detroit, John MacGregor was there as a Sergeant.  With the critical help of Indian Chiefs, Wyandotte and Tecumseh, the British Army and  Canadian Militias harassed the American militias in Michigan territory for about a year.  As a result, many Kentucky militiamen refused to fight in Upper Canada, as their terms of service forbade such an encounter.

By May of 1813, the British regulars had had enough in Michigan, with their most aggressive leader, Gen. Brock dead, and under the inept leadership of Col. Proctor, they retreated back into Upper Canada.  

Sergeant MacGregor fought at the disastrous battle of Moraviantown, which left the Americans occupying a large tract of south-western Upper Canada for the duration of the war.  (This loss of territory was only offset by the rapid occupation of eastern Maine by troops from Nova Scotia and later seizures of several US forts in Michigan Territory.)

The Kent Militia went underground and Lieut. John MacGregor was their leader.  His guerrilla tactics in several skirmishes with the Americans earned him recognition as a brilliant leader and a tough taskmaster.

MacGregor's guerillas had been fighting and surviving in the wilderness for an entire winter.  In the battle of Longwoods, in late February of 1814, he fought against superior odds, in spite of the stubbornness of senior British officers and their contempt for colonial militias, to send the American forces reeling back to Detroit.  He lost an arm in an action where he led a rearguard attack to save threatened British regular Army troops from disaster.  For this gallant action, he was awarded his Captaincy.

Renamed by John MacGregor, (in memory of his former New York unit) the "Loyal Kent Volunteers", succeeded in harassing the American forces in Michigan and northern Ohio.    MacGregor and his militia were given all the difficult travel assignments, roaming the entire area with their Indian comrades, at will, daring the Americans to put up a fight.