To trace twelve generations of our Bailey lineage is to watch the physical expansion of the United States unfold in real time. Our family did not merely observe American history—they cleared its forests, built its towns, fought its wars, and plowed its frontiers from the Puritan timberland of Connecticut to the timbered mountains of the Pacific West.Biographical & Historical Discoveries
Generation 1: The Immigrant Roots & Cutlers of Sheffield
- John Bailey (c. 1618–1696): Beyond his civil posts as viewer of chimneys, ladder inspector, and constable in Hartford, John’s migration down the Connecticut River in May 1662 to co-found Thirty Mile Island (Haddam) placed him on the outer edge of colonial defense during King Philip's War (1675–1676).
- His wife Lydia Backus (1637–1696) & Allied Backus Line: Modern genealogical consensus links her father, William Backus (c. 1606–1664), directly to Sheffield, Yorkshire. William was an apprentice cutler admitted to the Sheffield Cutlers Company. When he died in Norwich, CT, he signed his will with his unique "W over B" cutlery maker's mark and left his metalworking tools to his son—a craftsman legacy that has resonated through centuries down to my own furniture workshop!
Generation 2 & 3: Deepening Connecticut Roots
- Elizabeth Gerard (1671–1728) & Allied Line: Wife of John Bailey II. Her grandfather, Captain Matthew Beckwith, was an early Connecticut colonist, linking the Baileys to early New London and Lyme settlements.
- Deborah Brainerd (1698–1745) & The Brainerd Dynasty: Wife of Ephraim Bailey. The Brainerds were among the most influential families in Middlesex County. Her father, Deacon James Brainerd, was a Deputy to the Connecticut General Assembly and a major land proprietor in Haddam, solidifying the Baileys' standing in civic and church affairs.
Generation 4: Colonial Wars & The Revolutionary Frontier
- Oliver Bailey (1738–1822): A true veteran of early American warfare. During the French and Indian War, Oliver served in the Connecticut provincial regiments (appearing on rolls for the campaigns of 1758–1762). During the Revolutionary War, Oliver was a private in the 8th Company of Capt. Cornelius Higgins of Haddam, Col. William Douglas's 5th Battalion, General Wadsworth's Brigade, raised in June 1776 to reinforce George Washington's army at New York; he fought in the Battles of Long Island and White Plains.
- His wife Hannah Scoville (1739–1826) & The Scoville Metalworkers: Hannah’s family were early proprietors of Haddam and Middletown, known throughout Connecticut for brass-founding, blacksmithing, and land speculation.
Generation 5 & 6: Crossing the Appalachians to the War of 1812
- Thomas Bailey (1765–1854) & Esther Smith (1768–1810): Esther’s father, Lt. William Smith, was an officer in the Connecticut Continental Line during the Revolutionary War. Around 1800–1806, Thomas and Esther joined the post-Revolutionary exodus westward, leaving Connecticut to clear new land in Canton Township, Bradford County, Pennsylvania.
- Smith Bailey (1789–1862) & The War of 1812: Born in Connecticut and raised in Pennsylvania, Smith served in the Pennsylvania Militia during the War of 1812. Following his service, he pushed into the Ohio wilderness (Muskingum and Franklin Counties) before taking his family into the freshly opened Iowa Territory in 1845.
- Smith’s wife Rosemanty Rogers (1789–1843): Daughter of Zephaniah Rogers, a private in the Connecticut Line during the Revolution who drew a federal pension for his wartime service.
Generation 7 & 8: Prairie Pioneers & The Civil War Tragedy
- Orange Bailey (1811–1905): His long life bridge-headed three distinct frontier eras: the Pennsylvania woods, the Ohio prairie, and 60 years in Marion Township, Davis County, Iowa Territory.
- David Solomon Bailey (1837–1915): Enlisted on August 15, 1861, in Company G, 3rd Iowa Volunteer Cavalry. He saw extensive action across Missouri and Arkansas before the fateful Battle of Brice's Cross Roads (Mississippi) on June 10, 1864. Outnumbered Union forces under Gen. Samuel Sturgis were crushed by Confederate Gen. Nathan Bedford Forrest. David was severely wounded, losing his leg on the battlefield, and was captured. After surviving a Confederate field hospital and prison swap, he returned home to homestead in Elkhorn, Douglas County, Nebraska.
Generation 9, 10 & 11: The Northern Pacific Trail to California
- David Jackson Bailey (1865–1949) & Lillian Amanda Pierce (1867–1957): Married on the Nebraska frontier. Lillian brought elite New England heritage into the family—she was the daughter of Marcus Morton Pierce, a Union Civil War veteran, and a direct 10th-generation descendant of 1633 Charlestown founder Thomas Pierce. Driven by late 19th-century economic and farming busts in Nebraska, they moved west to Kendrick, Latah County, Idaho, before settling along the Clearwater and Snake Rivers in Lewiston.
- Franklin Jackson Bailey (1886–1968): Born in a Nebraska soddy homestead, Franklin filed a dryland homestead claim near Kalispell, Flathead County, Montana, in 1912. In 1918, he removed to Kendrick, Idaho, to try wheat farming, before moving again to Lewiston, Idaho. After being wiped out by the Great Depression, he packed up his family—including young Velma Veda Bailey (1914–2004)—and completed the final leg of the transcontinental march, settling in Southern California.
12 Generations of the Bailey Migration
1636: Hartford & Haddam, CONNECTICUT (John Bailey I & II, Ephraim)
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1800: Canton, Bradford Co., PENNSYLVANIA (Oliver & Thomas)
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1821: Muskingum & Franklin Co., OHIO (Smith & Orange)
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1845: Marion, Davis Co., IOWA Territory (Orange & David Solomon)
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1868: Elkhorn & Valley Co., NEBRASKA (David Solomon & David Jackson)
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1903: Kendrick, IDAHO & Kalispell, MONTANA Homestead (Franklin Jackson)
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1928: Los Angeles & Chatsworth, CALIFORNIA (Velma Veda & Jerry)
Narrative: The Long Trail West (1636–1942)
Chapter I: The Connecticut Timberland
In May 1662, twenty-eight men stepped into the shadows of the dense hardwood forests along the lower Connecticut River to clear a place called Haddam. Among them was John Bailey, a former constable and chimney viewer from Hartford. With his wife Lydia Backus—daughter of a Sheffield cutler who had traded his English anvil for the New World—John carved out a farm in the Higganum rocks.
For four generations, the Baileys were fixtures of Middlesex County. They served as town constables, church deacons, and provincial militiamen. When the French and Indian War erupted in the 1750s, Oliver Bailey shouldered a musket in the Connecticut provincial forces. Two decades later, as an older man, Oliver again answered the drumbeat of the American Revolution, defending the Connecticut line while his father-in-law's kin forged iron and brass for the colonial cause.
Chapter II: Crossing the Appalachians to the Ohio Country
By the close of the 18th century, the rocky soil of Connecticut could no longer support its expanding families. In the early 1800s, Oliver’s son, Thomas Bailey, and his wife Esther Smith joined a wagon train heading over the mountains into northern Pennsylvania, clearing timber in Canton, Bradford County.
War called the family once more in 1812. Thomas’s son, Smith Bailey, marched off with the Pennsylvania Militia. When he returned, the westward fever took hold again. By 1821, Smith had packed his young son Orange into a wagon, driving deeper into the frontier of Muskingum and Franklin Counties, Ohio.
Chapter III: The Iowa Frontier & The Battle at Brice's Cross Roads
In 1845, just as Iowa was preparing for statehood, Orange Bailey packed $1.50 in savings, his wife Lydia, and four young children into a covered wagon bound for Marion Township, Davis County, Iowa Territory. Within two years, tragedy struck—Lydia died in the crude log cabin Orange had built, leaving him alone with four small children on an unbroken prairie. Orange persevered, remarried, built a 110-acre farm, and fathered twenty children across his long 94-year life.
His second son, David Solomon Bailey, grew up with dirt under his nails on the Iowa frontier. When the Civil War moved toward Iowa in 1864, 26-year-old David enlisted in the 3rd Iowa Cavalry. He rode through the dust and mud of the Western Theater.
Then came June 10, 1864. At the Battle of Brice’s Cross Roads in Mississippi, the 3rd Iowa was caught in a brutal heatwave and a savage Confederate ambush. A bullet shattered David's leg; he was captured on the field and endured a bloody field amputation by army surgeons. Surviving captivity and infection, David returned to Iowa with an empty pant leg folded and pinned—a living symbol of the war's toll.
Chapter IV: The High Plains & The Timber of the Northwest
Undeterred by his lost limb, David Solomon Bailey hitched his horses and pushed west into Douglas County, Nebraska, in the late 1860s, establishing a farm and teamster business in Elkhorn. His son, David Jackson Bailey, came of age working as a cowboy on the wind-swept Nebraska plains, before marrying Lillian Amanda Pierce—herself the daughter of a Union soldier and Nebraska homesteader.
As economic panics and farming hardships struck the Midwest in the late 1890s, David Jackson and Lillian looked further west. They boarded the Northern Pacific line, moving their family to the timbered hills of Kendrick, Idaho, and later to the river valleys of Lewiston.
Their son, Franklin Jackson Bailey, inherited every ounce of his ancestors' pioneer wanderlust. In 1912, Franklin traveled to the Flathead Valley of Montana, filing a homestead claim near Kalispell. There, in the shadow of the Rocky Mountains, his daughter Velma Veda Bailey was born in 1914.
Chapter V: Sunset on the Pacific
By 1918, dryland farming in Montana had succumbed to drought and economic depression, so Franklin hitched his Belgian draft horses to a wagon and made the 300-mile trek back across the mountains to Kendrick, Idaho, to try his hand at wheat farming. He moved again in the late 1920s to Lewiston Orchards, where he farmed until being wiped out by the Great Depression. In the mid-1930s, Franklin Jackson Bailey made the final decision that completed his family’s three-century trek across the continent: he moved his family south to Los Angeles, California.
When Jerry, aka A Drifting Cowboy, was born in 1942, the journey that began in the Puritan woods of 1636 Hartford had reached the shores of the Pacific Ocean. Twelve generations of carpenters, cutlers, soldiers, homesteaders, horsemen, and farmers had carried the Bailey name across three thousand miles of American wilderness.
Thank you Gemini AI for your wisdom and research assistance. -- Drifting Cowboy
