Our Bailey Family: The Long Trail West (1636–1942)

 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

From Microfiche to AI: A Cowboy’s Guide to Family History

 

"You have the kindling and the matches... what you do with them is up to you."

Around 1972, my Aunt Muriel handed me three yellowing, typewritten pages titled "Lydia Corrina Brown-Bailey's Notes." Grandma Lydia had jotted down what she remembered of the family line, and Muriel added her own memories—including a colorful tidbit about her great-grandfather, David Solomon Bailey, a Civil War veteran who had lost a leg in the service of the Union.

Muriel reckoned David’s father was named Orange Green Bailey, and figured he must have been an Irishman who fled to America during the 1840s Potato Famine. "Orange," after all, sounded like a proper Irish name.

I tucked those three pages away. For the next twenty years, between a high-demand career in the home building industry and raising a family, there wasn't a spare minute to chase down dead relatives. The past would just have to wait.

The Cowboy & The Dial-Up Era

By 1992, I traded corporate boardrooms for a woodworking shop, launching a business crafting cowboy folk-art furniture. When custom orders were slow, I picked up consulting work for a major bank in Southern California. That gig required a whole new set of tools: a personal computer, a scanner, a printer, and this newfangled thing called an email address.

Remember AOL? The screech of the 14.4k modem became the background track of my evenings.

[1972] 3 Typewritten Pages

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[1995] cowboyup.com & Dial-Up (RootsWeb, GenWeb, Surname Mailing Lists)

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[1998] Mormon Microfiche Readers & Early Ancestry.com

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[2026] 40.9 MB PDF | 7,724 Pages | 9,000+ Names | AI Research Partner

By 1995, I registered the domain cowboyup.com. When I wasn't shaping timber, I was dipping my toes into the world of digital genealogy. In those early days, research was a wild frontier. We gathered on RootsWeb, GenWeb, and surname mailing lists, posting queries into the digital void and hoping a distant cousin in Ohio might read it. Every now and then, I’d head over to a local Mormon Church history center, cranking through reels of microfiche under the dim glow of a reader screen until my eyes crossed.

When Ancestry.com popped up around 1998, I subscribed, canceled, and re-subscribed a dozen times before finally settling in for the long haul.

Fast forward twenty-seven years: those three typewritten pages have expanded into an accurate, fully cited family tree of over 10,000 names—with a 40-generation pedigree chart spanning 7,724 pages and a 40.9-megabyte PDF file.

And as for Orange Bailey? He wasn't a 1840s Irish famine refugee at all. He was the direct descendant of John Bailey, a founding settler of Haddam, Connecticut, who stepped ashore in 1636.

The AI Frontier: A New Tool in the Shop

Last year, I decided to test a new kind of chisel: Artificial Intelligence.

After a few false starts, I settled into a groove with two AI platforms that act as hyper-efficient research assistants. But like any heavy machinery, AI comes with a warning label: it can and will make mistakes. If you don't know your subject reasonably well before you start, AI will happily lead you straight off a cliff with supreme confidence.

Used correctly, though? It uncovers obscure primary records, translates old documents, and helps synthesize centuries of scattershot data in seconds.

Which brings me to a young man named RA.

Kindling and Matches

A few days back, a new DNA match popped up on my dashboard: a young guy, RA. He had a bare-bones tree of just 23 people, but I immediately spotted two names: Nellie (my 2nd cousin) and Marcus (my grand uncle).

I felt that familiar spark—the joy of passing the torch. I shot him a message:

"Nellie gave me a photo of Orange Bailey 30+ years ago, 60 years ago I played horseshoes with Marcus, if you are interested I can guide you back to 1636 Baileys in Connecticut..."

RA wrote back promptly. He was fascinated, touched by his middle name being Bailey, and expressed a genuine sense of kinship. But then came the classic modern line:

"One thing I'm a little concerned about is your use of AI in your recent blog posts. I know AI can be a useful tool, but it can also be confidently wrong at times, so I just wanted to make sure you're fact-checking anything it helps with."

I couldn't help but smile. Here was a newcomer—holding a 23-person tree—cautioning a guy who’s spent 50 years in the archives about fact-checking.

I replied with the patience that only five decades of brick walls can teach you:

"AI is useful if you are careful. I've been studying our family history since the 1970s... What I get from AI is new information from sources I don't have access to or even know about. Coupled with DNA results, AI has absolutely broken down some brick walls. Below is a Bailey family lineage you can tap into if you want. Not a bit of this is from AI... You have the kindling and the matches... what you do with them is up to you."

The Trail Ahead

I haven't heard back from RA yet. As any veteran researcher knows, you often don't. Genealogy is a calling that catches people in its own time—usually when they're older, quieter, and looking in the mirror wondering where their story came from.

From three typewritten pages in 1972 to microfiche in 1998, to AI-driven DNA mapping in 2026, the technology changes, but the core work remains identical: searching for the truth of who came before us.

Tools don't build a house—carpenters do. AI won't write your family history for you, but if you know how to handle the tool, it sure makes the timber fit together a whole lot smoother.

Thank you Gemini AI for your wisdom and research assistance. -- Drifting Cowboy

Our Pierce Family: Massachusetts Bay to the Pacific Coast

 

This is a remarkable New England lineage that tracks nearly 350 years of American expansion—starting with Puritan settlement in 1630s Massachusetts, through colonial Connecticut and Rhode Island, into the post-Civil War Great Plains, and reaching the Pacific Northwest.

Key Genealogical Discoveries & Historical Notes

1. The Puritan Founders in Massachusetts (Gens 1–2)

• Thomas Pierce (1583–1666): Arrived in New England around 1633–1634 during the Great Migration. He was admitted as a freeman of Charlestown, Massachusetts, in May 1635 and became a major landholder with over 90 acres across Charlestown and Woburn. Notably, his 1665 will included a bequest of 20 shillings to Harvard College, making him one of the institution's earliest private donors.
• Sergeant Thomas Pierce II (1617–1683): Served as a Selectman of Woburn and held the rank of Sergeant in the local trainband (militia). His father-in-law, Rice (Ryse) Cole, was one of the original founders of the church in Charlestown in 1632.

2. The Connecticut & Rhode Island Branches (Gens 3–8)

• Col. Timothy Pierce (1673–1748): A towering figure in Eastern Connecticut history. He was among the earliest proprietors of Plainfield, CT. Over his life, he served as Colonel of the 11th Connecticut Regiment, Judge of the Probate Court, Judge of the County Court of Common Pleas, and represented Plainfield in the Connecticut General Assembly for nearly a decade.
• Jedediah Pierce (1740–1826): Born in Connecticut, Jedediah joined the post-Revolutionary migration up the Connecticut River valley into Vermont, settling in Royalton, Windsor County, where he lived for over three decades until his death at age 86.
• The Rhode Island "Pearce/Pierce" Spelling Variant: Generations 7 and 8 settled in Foster, Providence County, Rhode Island. In Rhode Island civil and church records, the surname frequently alternated between Pierce, Pearce, and Pirce. They married into long-standing Rhode Island families, including the Mattesons, Cases, and Braymans.

3. Military Service & Western Expansion (Gens 9–12)

• James L. Pierce (1823–c. 1847): Died young around age 24 during the era of the Mexican-American War, with family records indicating he passed away at sea.
• Marcus Morton Pierce (1842–1882): Named after Marcus Morton (the 18th Governor of Massachusetts). He served as a Union soldier during the Civil War. After the war, he joined the westward land rush, moving his family from Pennsylvania to homestead in Valley County, Nebraska.
• Lillian Amanda Pierce & Franklin Jackson Bailey (Gens 11–12): Lillian married David Jackson Bailey (son of a Union veteran). Their son Franklin Jackson Bailey homesteaded in Montana before moving to California, bridging the pioneer era into the mid-20th century.

Lineage at a Glance

Gen	Individual	Life Dates	Primary Residence	Key Historic Note
1	Thomas Pierce	1583–1666	Charlestown, MA	Immigrant ancestor (c. 1633); Harvard donor
2	Sgt. Thomas Pierce II	1617–1683	Woburn, MA	Selectman & Militia Sergeant
3	Thomas Peirce III	1645–1717	Woburn, MA / CT	Early settler in New Haven Co., CT
4	Col. Timothy Pierce	1673–1748	Plainfield, CT	Colonel 11th CT Regt., Probate Judge
5	Nathaniel M. Pierce	1701–1775	Pomfret, CT	Windham County landholder
6	Jedediah Pierce	1740–1826	Royalton, VT	Migrated to Vermont land boom
7	William Pearce (Pierce)	1770–1841	Foster, RI	Established Rhode Island branch
8	William Pearce (Pierce)	1794–1875	Foster, RI	Married into Matteson & Austin lines
9	James L. Pierce	1823–c. 1847	Foster, RI	Lost at sea during Mexican-American War era
10	Marcus Morton Pierce	1842–1882	Woonsocket, RI / Nebraska	Union Army Veteran & Nebraska pioneer
11	Lillian Amanda Pierce	1867–1957	Nebraska / Washington	Westward migration to Pacific Northwest
12	Franklin Jackson Bailey	1886–1968	Nebraska / Montana / CA	Montana homesteader

Family Narrative: From Massachusetts Bay to the Pacific Coast

Chapter I: The Puritan Foothold (1630s–1700s)

The story begins in the spring of 1633, when Thomas Pierce and his wife Elizabeth left Norfolk, England, aboard a Puritans' ship bound for the Massachusetts Bay Colony. Settling in Charlestown, Thomas established himself as a prominent land proprietor and citizen. His son, Sergeant Thomas Pierce II, helped build the town of Woburn, defending the community during the turbulent early Indian conflicts as an officer in the local trainband.

By the third generation, Thomas Peirce III looked beyond Massachusetts. As the colonies expanded southward into Indian-ceded lands, his son Timothy Pierce became one of the key figures in settling Plainfield, Connecticut.

Chapter II: Judges, Militiamen & Rhode Island Farmers (1700s–1840s)

In Eastern Connecticut, Col. Timothy Pierce rose to immense civic stature. As commander of the 11th Connecticut Regiment and a presiding judge in Windham County, Timothy represented the pinnacle of colonial leadership. His grandson, Jedediah Pierce, carried the family spirit into the revolutionary era—eventually moving north into the rugged hills of Royalton, Vermont.

Simultaneously, Jedediah’s son William Pearce established roots in Foster, Rhode Island. For two generations, the family farmed along the Rhode Island-Connecticut border, intermarrying with pioneer families like the Cases, Mattesons, and Braymans.

Chapter III: War, Tragedy & The Great Plains (1840s–1880s)

Tragedy struck the line in the late 1840s when James L. Pierce died young at sea during the Mexican-American War, leaving his young widow Elvira and small children in Rhode Island.

His son, Marcus Morton Pierce, answered the call to arms during the Civil War, enlisting in the Union forces. Following the war, Marcus joined the Homestead movement. Driven by the promise of free prairie land, he moved his family out to the Nebraska frontier, settling in Valley County.

Chapter IV: Crossing the Continent (1880s–1960s)

Marcus’s daughter, Lillian Amanda Pierce, grew up on the Nebraska prairie, marrying a young cowboy David Jackson Bailey (himself the son of a Union Civil War veteran).

Their son, Franklin Jackson Bailey, continued the frontier tradition by filing a homestead claim in Montana, before farming in Idaho and eventually moving his family to Los Angeles, California. In twelve generations, our Pierce line traveled from the shores of Charlestown Harbor across the Great Plains to the Pacific.

Thank you Gemini AI for your wisdom and research assistance. -- Drifting Cowboy