The story of early America is often told through grand political declarations, but it was forged by men who spent their youth in the heavy timber and high grass of raw battlefields. Our 6th great-grandfather, Oliver Bailey, was one of those rare colonial citizen-soldiers who bore arms in both epochal conflicts that defined North America: the French and Indian War and the American Revolutionary War.
From the blood-soaked abatis of French Fort Carillon to the desperate retreat across Long Island under George Washington, Oliver spent decades marching toward the sound of gunfire before laying down his musket to become a founding pioneer of Bradford County, Pennsylvania.
Part 1: Genealogical Overview & Timeline
- Born: June 25, 1738, in Haddam, Middlesex County, Connecticut.
- Died: October 14, 1822, in Granville Township, Bradford County, Pennsylvania (Aged 84).
- Military Legacy: Serviceman in the French and Indian War (1758, 1759, 1760) and Private in the Revolutionary War (1776).
Generational Military Lineage
Oliver established a tradition of service that carried through generations of our family tree:
- Oliver Bailey (1738–1822) — 6th Great-Grandfather: French and Indian War & American Revolution.
- Thomas Bailey (1765–1854) — Son: War of 1812.
- Smith Bailey (1789–1862) — Grandson: War of 1812 (Husband of Rosemanty Rogers).
- Orange Bailey (1811–1905) — Great-Grandson.
- David Solomon Bailey (1837–1915) — 2nd Great-Grandson: Union Soldier, Civil War.
- David Jackson Bailey (1865–1949) — 3rd Great-Grandson.
- Frank Jackson Bailey (1886–1968) — 4th Great-Grandson: Montana Militia, World War I.
Part 2: Fighting for the Crown — The French & Indian War (1758–1760)
As a young man in his twenties living in Haddam, Connecticut, Oliver entered provincial service to fight for the British Crown against the French and their Native allies in the wilderness of upper New York and Canada.
Oliver's French & Indian War Campaigns
1758: Fort Carillon (Ticonderoga) ──► 3rd CT Regiment (Col. Fitch)
│ Bloodiest defeat; faced French entrenchments
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1759: Fall of Ticonderoga ──────────► 1st CT Regiment (Maj. Gen. Lyman)
│ British capture the fort under Gen. Amherst
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1760: Montreal Campaign ────────────► 2nd CT Regiment (Col. Whiting)
│ Served as Regimental Drummer; French surrender
1758: The Disaster at Fort Carillon
Enlisting in Capt. Jonathan Latimer’s Company of Col. Eleazar Fitch’s 3rd Connecticut Regiment, 20-year-old Oliver was marched north into the Lake George wilderness under British General James Abercrombie.
On July 8, 1758, Abercrombie ordered a frontal assault against French General Marquis de Montcalm’s heavily fortified position at Fort Carillon (later renamed Fort Ticonderoga). Without waiting for field artillery, thousands of British and Provincial troops charged into a maze of sharpened, fallen trees (abatis) under devastating volley fire. It became the bloodiest battle of the war, leaving over 2,000 British casualties.
A Family Twist on the Battlefield: In an incredible stroke of genealogical fate, while young Oliver Bailey was charging the logs at Carillon with the Connecticut provincials, another of our grandfathers—Michel Vielle (our 5th great-grandfather)—was stationed behind those very same log walls as a French soldier in the RĂ©giment de la Reine. Two ancestors, fighting under different flags, facing each other across the smoke of the same timber barrier.
1759: The Capture of Ticonderoga
Determined to erase the 1758 defeat, Oliver re-entered service in 1759 with Maj. Gen. Phineas Lyman’s 1st Connecticut Regiment. Under General Sir Jeffery Amherst, the British army returned to Fort Carillon. Outmaneuvered, the French garrison blew up the powder magazine and retreated. Oliver and his unit helped occupy the fallen stronghold, officially renamed Fort Ticonderoga.
1760: The Montreal Campaign & The Fall of New France
By 1760, Oliver had earned the responsibilities of a Regimental Drummer in Capt. Ichabod Scranton’s 5th Company, Col. Nathan Whiting’s 2nd Connecticut Regiment. Drums were the tactical communications system of 18th-century armies, signaling assembly, marches, and battlefield orders.
Oliver beat the drums as part of General Amherst’s three-pronged convergence on Montreal. Surrounded by 18,000 British and provincial troops, the French civilian governor surrendered on September 8, 1760, ending French colonial rule in Canada and completing the conquest of New France.
Part 3: Fighting for the Republic — The Revolutionary War (1776)
Sixteen years after helping win North America for the British King, Oliver Bailey took up his musket again—this time to fight against the Crown.
1776 Revolutionary Campaign
June 1776: Enlists in Capt. Higgins' Co., Col. Douglas' 5th CT Battalion
│
August 1776: Battle of Long Island (Brooklyn Heights)
│ Fought in largest battle of the war; survived Washington's retreat
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October 1776: Battle of White Plains
Fought British flank maneuvers in Westchester County, NY
In June 1776, as the Continental Congress prepared to sign the Declaration of Independence, 38-year-old Oliver enlisted as a Private in Capt. Cornelius Higgins’ 8th Company, within Col. William Douglas’s 5th Connecticut Battalion (Wadsworth’s Brigade). His unit was rushed directly to New York to reinforce General George Washington’s fledgling Continental Army.
The Battle of Long Island (August 27, 1776)
Oliver arrived in New York just in time for the largest land battle of the entire Revolutionary War. Holding positions on Long Island, Washington’s army was outmaneuvered when British General Howe landed 32,000 troops and flanked the American line through Jamaica Pass.
Oliver’s Connecticut battalion was thrust into the chaos of the retreat toward Brooklyn Heights. While the heroic stand of the "Maryland 400" bought time, Oliver and his comrades held the inner defensive lines until the night of August 29–30, when Washington executed a daring, silent evacuation across the East River into Manhattan under cover of fog—saving the army from total destruction.
The Battle of White Plains (October 28, 1776)
Driven north out of Manhattan, Washington’s army made a stand at White Plains in Westchester County. On October 28, Howe attacked the American high ground on Chatterton Hill. Oliver’s battalion engaged British and Hessian troops in heavy fighting before Washington ordered a tactical retreat further north into the highlands. Having served out his campaign season during one of the most perilous stretches of the war, Oliver returned home to Connecticut.
Part 4: The Bradford County Pioneer (1790s–1822)
Following the Revolution, Oliver joined the wave of Connecticut veterans seeking land in Pennsylvania's Northern Tier. In the late 1790s, he settled in Granville Township, Bradford County, Pennsylvania.
In the rugged hills along the Towanda Creek watershed, Oliver cleared land, built a homestead, and established his family as foundational pioneers of the county. He lived out his remaining years surrounded by children and grandchildren who would themselves answer the nation’s calls to duty in the War of 1812 and the Civil War.
Oliver Bailey passed away on October 14, 1822, at the age of 84. He was laid to rest in the soil of Granville Township—a veteran who had beaten the drum for the British Empire in the northern wilderness and stood shoulder-to-shoulder with Washington's troops to birth a new republic.
Thank you to Gemini AI for your wisdom and research assistance. — Drifting Cowboy


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