Thomas Shailer: Lost at Sea in the West Indies (1706)

 

Part 1: Filling in the Historical Details (1706)

The disappearance of Thomas Shailer is documented in early Connecticut probate and town records. It contextualizes a very specific, dangerous era of American colonial history.

The Trade: The Provisions and West Indies Triangles

Haddam sat directly on the navigable waters of the Connecticut River. Settlers quickly realized that clearing timber and growing surplus crops could be highly profitable if shipped out.

By 1700, Connecticut towns regularly sent livestock, barrel staves, salted meat, and timber downriver to New London or Boston, where ships departed for Jamaica, Barbados, and the Leeward Islands. The vessels traded these provisions for molasses, sugar, and rum. Thomas Shailer was directly engaged in this lucrative, high-risk river-and-sea commerce.

The Disaster: Queen Anne's War (1702–1713)

When Thomas Shailer’s ship vanished in the winter of 1705/1706, the Atlantic and Caribbean were active war zones. During Queen Anne's War, French and Spanish privateers heavily targeted English merchant shipping lanes.

A vessel sailing south from New England faced three primary threats:

1. Privateers: Armed commerce raiders operating under letters of marque.
2. The Windward Passage Piracy: Unsanctioned outlaws operating out of isolated coves in western Hispaniola and the Bahamas.
3. Winter Atlantic Gales: Violent storms off Cape Hatteras or within the Caribbean basin.

The Legal Limbo

Because no body was recovered and no eyewitnesses returned to confirm the ship's fate, Connecticut authorities could not issue an immediate death certificate. Thomas's estate records note his death date as March 3, 1706, but this was a retroactive legal consensus date designated by the probate court so his property could finally be inventoried and distributed to his widow, Marah, and his children after months of silence.

Part 2: Lineage Analysis & Intersections

The lineage traces a path from the initial hard-scrabble settlement of Connecticut, through the accumulation of maritime wealth, and into the post-Revolutionary migration to Pennsylvania.

[Gen 1] Thomas Shailer (Proprietor & Sea Trader) — Lost at Sea, 1706

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[Gen 2] Capt. Thomas Shailer (Militia Officer & Civic Leader)

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[Gen 3] Hannah Shailer ⚭ William Scoville (Landed Farmers)

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[Gen 4] Hannah Scoville ⚭ Oliver Bailey (Revolutionary Veteran) -> To Pennsylvania

Key Historical Highlights by Generation:

• Gen 1 (Thomas Shailer): The pioneer-adventurer archetype. He was one of the twenty-eight original buyers of the 1662 Haddam land grant (the "Thirty Coats" purchase). His willingness to risk capital on sea voyages reflects the shifting colonial economy toward merchant capitalism.
• Gen 2 (Capt. Thomas Shailer): He stabilized and grew the family's regional influence. Earning the title of "Captain" within the colonial militia, he was an elite civic figure in Haddam. This generation moved from raw survival to establishing a permanent dynastic presence along Candlewood Hill.
• Gen 3 (Hannah Shailer): Her marriage to William Scoville combined two major colonial families. The Scovilles were prominent early landholders, shifting the family's focus back toward extensive agricultural development and local milling operations.
• Gen 4 (Hannah Scoville): This generation witnessed the birth of the Republic. Her marriage to Oliver Bailey brings in the veteran pedigree of the Wadsworth Brigade (reinforcing Washington at New York). Hannah survived her husband by four years, dying at the age of 87 in Granville, Pennsylvania, representing the family's post-war migration out of Connecticut into the western frontier.

Part 3: Lost in the West Indies: The Vanishing of Proprietor Thomas Shailer

Celebrating America 250

To look at a colonial family tree is to look at a map of calculated risks. Some ancestors risked everything by pushing west into the dense, trackless forests of the American frontier. Others looked toward the horizon, betting their lives and fortunes on the churning, unpredictable waters of the Atlantic trade routes.

As we celebrate America 250, our timeline brings us back to the rugged origins of Haddam, Connecticut, and the mystery of our ninth great-grandfather, Thomas Shailer (c. 1643–1706). He was a man who conquered the wilderness of the Connecticut River Valley, only to be swallowed up by the sea.

From Stratford-on-Avon to the Thirty Coats

Thomas Shailer was born in the historic heart of England, at Stratford-on-Avon, but arrived in New England as a young man with a fierce appetite for land and enterprise. In 1662, he secured his place in history as one of the original twenty-eight proprietors who executed the legendary "Thirty Coats" purchase from the local Niantic leaders, establishing the settlement of Haddam along the banks of the Connecticut River.

For decades, Thomas did the heavy work of empire-building. He cleared the rocky soils, established an agricultural footprint, raised a family with his wife, Marah Alice Spencer, and helped govern the growing wilderness outpost.

But Haddam had a distinct advantage over inland towns: it sat directly on a deep-water river highway. As the decades rolled on, the timber and agricultural surpluses cleared by the settlers began filling the hulls of small merchant sloops and brigantines. The maritime trade lanes were calling, and Thomas Shailer answered.

The Fatal Run to Jamaica

By the dawn of the 18th century, Connecticut had become an essential cog in the West Indies trade triangle. Ships departed the Connecticut River laden with timber, barrel staves, livestock, and salted provisions bound for sugar plantations in Jamaica and Barbados. They returned with valuable cargoes of sugar, molasses, and cash.

It was highly lucrative, but in the winter of 1705/1706, it was also exceptionally lethal.

The nations of Europe were locked in Queen Anne's War (1702–1713). The Caribbean was swarming with French privateers, Spanish warships, and opportunistic pirates operating out of the Bahamas. Combined with the constant threat of sudden Atlantic winter gales, every voyage south was a brush with death.

Around the turn of that fateful year, Thomas boarded a trading vessel bound for Jamaica. The ship slipped down the Connecticut River, entered the open ocean, and vanished from the pages of history.

Did a sudden tropical hurricane snap the masts and send the vessel to the bottom? Or did a ruthless privateer crew intercept them, seize the cargo, and leave no survivors? We will never know. Thomas Shailer was never heard from again.

The silence was so absolute that the Connecticut probate courts sat in legal limbo for months, unable to settle his affairs because no one could verify the exact day or place of his passing. Eventually, the court established a legal date of death: March 3, 1706. His estate was partitioned, and his widow and children were left to carry on his legacy on dry land.

The Lineage of Resilience

The sea took Thomas, but it could not break the line he planted in the Connecticut soil. His son, Capt. Thomas Shailer (1670–1753), rose to become a foundational pillar of Haddam, serving as an officer in the colonial militia and navigating the town through decades of growth.

Through the marriage of his granddaughter, Hannah Shailer, into the prominent Scoville family, the bloodline eventually merged with our Revolutionary War hero Oliver Bailey.

It is a striking generational arc:

• Our 9th great-grandfather fought the sea to build early colonial commerce.
• Our 6th great-grandfather fought the British Crown at Long Island and White Plains to secure American independence.

By the time Thomas Shailer's great-granddaughter, Hannah Scoville Bailey, closed her eyes for the last time in the hills of Bradford County, Pennsylvania, in 1826, the wild world her seafaring ancestor left behind had transformed into a sovereign, continental nation.

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

The Timber Barons of Kittery: Nathan Lord I

The maternal ancestry of Martha Lord (1667–1726)—mother to the centenarian Martha Littlefield—takes us directly into the foundation of Kittery and Berwick, Maine. The Lord family and their adjacent lines were prominent landowners, timber mill operators, and garrison commanders who bore the heaviest brunt of the early Anglo-Wabanaki border conflicts.

Our 9th great-grandfather, Nathan Lord I (c. 1630–1690), immigrated from Kent, England, and settled in Kittery (the part that later became Berwick) by 1652. He married Martha Conley, daughter of Abraham Conley, one of the region's earliest wealthy landholders.

• The Industry: Nathan Lord did not just farm; he partnered with his father-in-law to operate water-powered sawmills along the Asbenbedick (Salmon Falls) River. This region possessed some of the finest old-growth white pine in the world, heavily coveted by the Royal Navy for ship masts.
• The Strategic Target: Because timber mills were the primary economic engine of English expansion into Wabanaki territory, they became the highest-priority targets for French-backed indigenous raids during King William's War.

The 1690 Salmon Falls Massacre

The defining historical intersection for this generation occurred on March 18, 1690. A combined force of French soldiers under Quentin de West and Abenaki warriors launched a devastating surprise dawn assault on the settlement of Salmon Falls (Berwick).

                    THE 1690 SALMON FALLS ASSAULT

  

     French-Abenaki Strike Force ──────► Surprise Dawn Ambush (March 18)

                                              │

                                              ▼

     • Fortified Garrisons Breached ──────────► 30+ Settlers Killed / 50+ Captured

                                              │

                                              ▼

     • The Lord Family Response ──────────────► Nathan Lord I dies during the 

                                                wartime evacuation period.

The attack was brutal and systematic: fortified homes were burned, livestock was slaughtered, and more than 80 settlers were either killed or taken on the long march to captivity in Canada.

While our 8th great-grandmother Martha Lord (then a young married woman of 23) survived the initial onslaught, her father, Nathan Lord I, died later that same year amidst the disease, displacement, and ongoing skirmishes that crippled the region following the massacre.

The Tozer-Playstead Garrison Connection

Through Martha Lord’s siblings and cousins, the family line is inextricably linked to the famous Tozer Garrison of Berwick.

• The Sentry Stand: When the garrison was attacked during an earlier conflict (King Philip's War), a young girl held the door shut against Native warriors long enough for fifteen women and children—including members of the extended Lord and Littlefield families—to escape out the back into the safety of the main settlement.
• The Resilience: This constant state of siege meant that Martha Lord raised her children, including our 7th great-grandmother Martha Littlefield, with an acute defensive mindset. They learned to manufacture their own ammunition, ration provisions for long winters spent entirely inside stockades, and maintain independent trade networks along the coast when land routes were cut off.

The Core Lineage Blueprint

This maternal layer completes the foundational frontier grid of our family tree before they pivoted southwest into New Hampshire and ultimately returned to reclaim Boothbay:

Generation	Individual	Spousal Alliance	Regional Impact
Gen 1	Nathan Lord I (9th Great-Grandfather)	Martha Conley	Foundational timber mill pioneer of Kittery/Berwick; casualty of the 1690 King William's War era.
Gen 2	Martha Lord (8th Great-Grandmother)	Moses Littlefield (Captured 1692, Killed 1707)	Managed the exposed frontier holdings after her husband's capture and death; orchestrated the strategic retreat to Dover, NH.
Gen 3	Martha Littlefield (7th Great-Grandmother)	Thomas Stevens	The centenarian (101 years old) whose life bridged the raw, war-torn frontier straight into the Washington presidency.

The Frontier Crucible: Our Littlefield-Stevens Family in Maine

 

Our Littlefield-Stevens line contains some of the most dramatic, war-torn history on the early American frontier. When we dig beneath the birth and death dates of this branch, we find a family positioned directly in the crosshairs of the French and Indian Wars, defined by garrison attacks, captivity, and a major geographical pivot to Maine's maritime frontier.

The Frontier Crucible: The Capture of Moses Littlefield

To understand Martha Littlefield’s extraordinary century of life, you have to look at the violent world into which she was born. Her father, Moses Littlefield (1666–1707), lived on the absolute edge of the English frontier in Wells and Berwick, Maine.

During King William's War (1688–1697), French forces and their Wabanaki allies targeted these exact settlements to halt English expansion.

• The Captivity: In 1692, when Martha was just an infant, her father Moses was captured during a brutal raid on Wells.
• The Interrogation: He was marched through the wilderness into French Canada (Quebec). Because the Littlefield family comprised prominent regional surveyors and millwrights, Moses possessed vital intelligence about frontier fortifications. He was thoroughly interrogated by French authorities before eventually being ransomed back to Massachusetts years later.

This foundational trauma explains why Martha’s birthdate is an approximation (Abt. 1691). She spent her childhood inside fortified garrison houses, ducking behind stockades whenever the alarm riders came through.

The 1707 Tragedy: The Death of Moses Littlefield

The frontier never truly settled. During Queen Anne's War, the raids resumed. In March 1707, Moses Littlefield was killed in action during a sudden skirmish near Wells, Maine.

Martha was only about sixteen years old when her father was killed. Her mother, Martha Lord, was left to manage the family's exposed land holdings. To survive the ongoing conflict, the widowed Martha Lord pulled her children back south into the relative safety of Dover and Somersworth, New Hampshire.

This strategic retreat is exactly how our 7th great-grandmother Martha Littlefield met her husband, Thomas Stevens.

The Post-War Pivot: The Reoccupation of Boothbay

Our 6th great-grandmother, Olive Stevens (1717–1793), grew up in the safety of New Hampshire, but the pull of the Maine frontier remained in her blood. When she married the master blacksmith John Catland (Catlin), they executed a major post-war migration.

                  THE NORTHERN MARITIME PIVOT

  

    [Wells/Berwick, ME] ───────► [Dover/Somersworth, NH] ───────► [Boothbay/Bristol, ME]

     • Frontier raids.            • Post-1707 safety zone.         • Post-war reclamation.

     • Moses killed (1707).       • Martha marries Thomas.        • John Catland's Forge.

Following the fall of French Canada, the Maine coast suddenly opened for permanent English settlement. Olive and John Catland migrated straight to Boothbay and Bristol, Maine.

• This move was a deliberate reclamation. The Booth family (our ancestors via the master lineage) had originally surveyed and given their name to Boothbay a century prior before being driven out by the Indian Wars.
• By moving back, Olive Stevens and John Catland re-established the family's presence in the region, anchoring the local maritime economy with John’s revolutionary blacksmith forge.

Two Worlds, One Life: Martha's Century of Perspective

When Martha Littlefield died in Dover, New Hampshire, on Christmas Eve in 1792 at the age of 101, the local community recognized her as a living archive. Consider the staggering transitions her single eyes witnessed:

• The Currency: She went from using British pounds and wampum trade beads in a raw wilderness to holding the newly minted United States dollar.
• The Warfare: She grew up fighting matches against flintlock muskets and French raiders, survived the global campaigns of the American Revolution, and died under the constitutional presidency of George Washington.
• The Geography: She saw Maine transform from a blood-soaked, abandoned graveyard of ruined cabins into a booming, sovereign network of American shipping ports.

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

The Tragedy at Old Providence (1641)

 

Samuel Wakeman’s death wasn't just a random pirate attack; it was a consequence of high-stakes "Puritan Privateering."

The Mission: Cotton and Colonists

In 1641, the Puritan leaders of Massachusetts Bay were facing a severe economic depression. Samuel Wakeman (the father-in-law of our 9th great-grandfather) co-chartered a voyage to Old Providence Island (off the coast of modern-day Nicaragua, not to be confused with New Providence in the Bahamas). Their goal was twofold: trade New England goods for cotton and tobacco, and potentially relocate struggling settlers back to Massachusetts.

The Spanish Ambush

Unknown to Wakeman, the Spanish had finally reached their breaking point with the "heretic" colony on Old Providence, which had become a base for privateers raiding Spanish treasure ships. Just weeks before Wakeman’s arrival, a massive Spanish fleet had captured the island.

When Wakeman’s ship sailed into the harbor, they expected a friendly Puritan welcome. Instead, the Spanish forts opened fire. According to Winthrop's Journal, a cannon shot struck the ship, and flying splinters or a direct hit "sorely wounded" Wakeman in the thighs. He lingered for ten days in the tropical heat—likely battling gangrene—before dying. His death was a shock to the Hartford colony, where he was a highly respected figure and a frequent deputy to the General Court.

The Mythic Legacy: Isaac Potts and the Praying Washington

 

Beyond the Valley Forge house being rented to George Washington for his headquarters there’s one additional tale that needs to be told, in it--our cousin--Isaac Potts is the primary anchor of one of the most famous legends in American history.

According to a widely popularized account attributed directly to Isaac later in his life, he was a staunch Quaker pacifist who initially opposed the war. However, while riding through the woods near the Valley Forge encampment, he supposedly stumbled upon George Washington on his knees in the snow, deep in agonizing prayer for his starving troops.

The story goes that Potts was so deeply moved by Washington's profound faith and heavy burden that he returned home, converted to the Patriot cause, and told his wife that America would surely win its independence under such a leader.

While historians today debate whether this spiritual encounter in the woods was a literal occurrence or an idealized piece of early 19th-century Americana, the historical reality remains unassailable: our 1st cousin 8x removed, Isaac Potts, surrendered his homestead to shelter the Commander-in-Chief during the darkest pivot point of the American Revolution.

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

Burying the Guns: How Our Potts Cousins Saved Washington’s Artillery

 

Celebrating America 250

Every genealogist searches for the exact moment their family tree collides with a turning point in history. For our family, that collision didn't just happen in the halls of statecraft or on a standard battlefield line—it happened deep in the roaring, spark-showered interior of the early American iron industry.

As we approach the United States Semiquincentennial, much will be written about General George Washington’s winter headquarters at Valley Forge. Family historians widely know that the pristine stone house Washington rented for his command belonged to our first cousin eight times removed, the Quaker ironmaster Isaac Potts (1750–1803).

But there is a gritty, high-stakes prequel to the Valley Forge encampment that standard history books often omit. It is the story of Isaac’s brothers, Samuel and Thomas Potts, and a desperate, midnight operation to bury the heavy artillery of the Continental Army before the British could seize it.

The Heavy Metal Nerve Center of the Revolution

By 1776, the Potts family operated a massive, interconnected metallurgical empire across Pennsylvania. While Isaac managed the gristmill and shared ownership of the "Valley Forge" ironworks with his brother-in-law William Dewees, his brothers Samuel and Thomas ran the formidable Warwick Furnace in Chester County.

Warwick wasn’t a simple frontier blacksmith shop; it was an industrial powerhouse. When the war erupted, the Potts brothers cast aside their traditional Quaker pacifism to turn their furnaces into a primary munitions foundry for the Patriot cause. In 1776 alone, the Warwick Furnace successfully cast more than 60 heavy cannons for the infant Continental Army and Navy.

This massive production of grapeshot, muskets, and artillery pieces quickly placed a giant target on the backs of the Potts brothers. To the British high command, dismantling the Potts supply chain was just as critical as capturing Philadelphia.

The Disaster at Brandywine and the Retreat to Warwick

In September 1777, the dark reality of war arrived on the family's doorstep. Following the American defeat at the Battle of Brandywine on September 11, a torrential downpour ruined the Continental Army's gunpowder, leaving Washington’s troops virtually defenseless.

Needing an immediate industrial sanctuary to repair firearms, recast ammunition, and forge new weapons, Washington ordered a retreat directly to the Potts family's iron empire. For several tense days, the Warwick Furnace fields became a massive, muddy encampment. The furnace fires burned around the clock as the Potts brothers and their ironworkers labored furiously to re-equip the army.

But the British army, led by General Howe, was hot on their trail.

The Midnight Cache

As British scouts advanced toward Chester County, Washington realized his army had to move immediately. However, the heavy brass cannons—the pride of the Continental artillery—could not be moved quickly enough through the deep, rutted mud fields. If left behind, these guns would be captured, turned against the American lines, and used to crush the rebellion.

In a move calculated to protect both the army and the foundry, the Potts brothers executed a daring plan. Under the cover of darkness, while the final American regiments evacuated the property, Samuel and Thomas coordinated a massive excavation. Using their heavy draft teams and trusted ironworkers, they dragged the massive brass artillery pieces out into the furnace fields.

They dug deep trenches into the soot-stained earth and buried Washington’s cannons completely out of sight, carefully smoothing over the soil to blend with the surrounding landscape.

When the British forces finally raided the Warwick Furnace and the nearby Valley Forge ironworks a few days later, they burned buildings, destroyed equipment, and searched the grounds for weapons. But they missed the prize. The secret ordnance cache remained safely hidden beneath their feet.

Our Spot on the Timeline

Once the British moved on toward Philadelphia, the hidden cannons were safely exhumed and returned to the Continental Line, seeing action in the subsequent campaigns of the war.

Our direct lineage runs through Isaac, Samuel, and Thomas's aunt, Mary Potts (1688–1762), who married Mathias Tyson. Through this tightly bound Montgomery County cousin network, our family didn't just witness the American Revolution from afar. Our kin built the furnaces, cast the iron, sheltered the Commander-in-Chief, and literally buried the big guns that secured the birth of a new Republic.

Thank you Gemini AI for your wisdom and beautiful narrative. -- Drifting Cowboy