Plymouth Rock 1620 to "We the People" 1787 & Beyond: Our Family’s Footsteps Through the American Story

 

By: Drifting Cowboy aka Jerry England 

Celebrating America 250 

Every genealogist eventually hits a moment of profound realization: our ancestors did not live their lives in a vacuum. They weren’t just names on dusty parchment or statistics in a census ledger. They were flesh-and-blood actors walking the stage of history, breathing the smoke of the same conflicts that forged the United States, and building the physical infrastructure of the republic we inherit today.

As we march toward the Semiquincentennial in 2026, I wanted to take a bird's-eye view of our family tree. Instead of looking at individual branches in isolation, I have mapped our ancestors—the blacksmiths, the privateers, the teenage drummers, the frontier scouts, and the elite cavalrymen—directly onto the macro-timeline of early American history.

From the maritime mysteries of 1640s New Haven and the brutal, snow-covered stockades of King Philip’s War, to the freezing trenches of Valley Forge and the high-stakes horse charges of the War of 1812, this is the master timeline of how our direct kin traveled the long, bloody road from Plymouth Rock 1620, to "We the People” 1787, and Beyond 1812.

⚓ Early Exploration and Settlement (1620–1629)

1620: The Mayflower Lands at Plymouth

Our ancestral ties to the following foundational Mayflower passengers provide a window into the raw survival and governance of the 1620 settlement:

• Francis Cooke (c. 1583–1663) | 11th Great-Grandfather
• Role: A Leiden Separatist and signer of the Mayflower Compact. He arrived with his son John, while his wife Hester joined three years later on the Anne (1623).
• Richard Warren (c. 1578–1628) | 11th Great-Grandfather
• Role: A London merchant and signer of the Mayflower Compact. He braved the initial winter alone; his wife Elizabeth and five daughters followed on the Anne.
• Elder William Brewster (c. 1566–1644) | Paternal Grandfather of the Wife of our 9th Great-Grandfather
• Role: The spiritual anchor and senior elder of Plymouth. As the only university-trained founder, his theological philosophy fundamentally shaped early colonial civil law.
• Dr. Samuel Fuller (c. 1580–1633) | Father-in-Law of our 9th Great-Grandmother
• Role: The colony’s indispensable first physician, surgeon, and deacon, who frequently traveled to neighboring Salem and Charlestown to combat early epidemics.

1623–1628: The Pre-Bay Pioneer Influx

• Ancestral Intersection: John Rogers (c. 1606–1692) arrives in Plymouth Colony, quickly aligning his family with the Mayflower elite. His line eventually marries into the riches of the early Cape Cod and Rhode Island expansions.
• Ancestral Intersection: John Pierce (1588–1661) secures the early land patents from the Plymouth Company, establishing foundational family holdings in Watertown, Massachusetts, that anchor the upcoming Puritan vanguard.

1626: The Purchase of Manhattan & The New Netherland Dutch

• Ancestral Intersection: As Peter Minuit establishes New Amsterdam, our foundational New Netherland Dutch ancestors settle the Hudson River Valley. Through decades of strategic alliances, this resilient Knickerbocker line will directly intersect with the family of future President Martin Van Buren, forever linking our tree to the unique cross-cultural roots of early New York.

🪓 Growth and Consolidation (1630–1675)

1630: John Winthrop Founds Boston & The Great Migration

• Ancestral Intersection: Captain George Denison arrives as an 11-year-old boy aboard the Lion (1631). He is tutored by the famed "Apostle to the Indians," Reverend John Eliot, absorbing the indigenous customs that would later dictate his frontier warfare tactics.
• Ancestral Intersection: Thomas Plympton (1620–1676) arrives from Sudbury, England, as an original founder of Sudbury, Massachusetts. He carves out a massive agricultural footprint along the treacherous western flank of the Massachusetts Bay.

1636: The Fracturing of New England (CT & RI Founded)

• Ancestral Intersection: John Catlin II (Cattell) arrives as an immigrant and pushes deep into the Connecticut River Valley, establishing his homestead at Wethersfield to secure the agrarian frontier.
• Ancestral Intersection: Captain George Lamberton dominates the New Haven Colony as a merchant prince. He challenges the Dutch fur monopoly by driving English commerce south into the Delaware River Valley, facing arrest and trial at Fort Amsterdam (1642).

1646: The Ship of Air Maritime Disaster

• Ancestral Intersection: Captain George Lamberton commands the ill-fated "Great Ship" out of New Haven. The vessel vanishes into the Atlantic, prompting the famous atmospheric phantom ship sighting in New Haven Harbor (1647) immortalized by Mather and Longfellow.

1651–1673: The Navigation Acts & Border Surveying

• Ancestral Intersection: Robert Booth (1602–1672) acts as a foundational surveyor and magistrate along the Maine coast, officially naming and mapping the deep-water harbor of Boothbay, staking an early claim for independent English timber infrastructure.
• Ancestral Intersection: John Rogers II expands his merchant estate into the Narragansett region, navigating the tightening British trade maritime laws by establishing independent coastal trade networks.

1654: The Mystic Land Grant

• Ancestral Intersection: For his elite militia service, Captain George Denison is granted 200 acres by Governor John Winthrop Jr. along the Pequotsepos Brook, laying out the historic Pequot Trail with his surveyor's chain.

1662: The Thirty Coats: The Forging of Haddam, Connecticut

• Ancestral Intersection: Our ancestors participate in the legendary purchase of the lands that would become Haddam, Connecticut. Traded from the local Western Niantic sachems for thirty plush coats, this transaction establishes the bedrock Connecticut farming community where our Bailey and allied lines will act as civic anchors for over a century.

🛡️ Transition to Royal Control (1676–1700)

1675–1676: King Philip’s War Erupts

• Ancestral Intersection: Captain George Denison fortifies his log-and-stone manor with a heavy stockade. He integrates European cavalry tactics with Mohegan and Pequot scouts on his "militia meadow." His company successfully captures Canonchet, Chief Sachem of the Narragansetts, decisively breaking the southern theater of the war.
• The Ultimate Sacrifice: On April 18, 1676, our 9th great-grandfather, Thomas Plympton, is ambushed and killed by Native warriors while desperately trying to escort a neighboring family to the safety of the fortified Sudbury Garrison. His death stands as a central pillar of the town's wartime folklore.
• The Garrison Defenders: The Pierce and Bailey families of Watertown and Newbury form immediate volunteer units, garrisoning their stone homesteads and defending the strategic Merrimack and Charles River corridors from being completely overrun.

1689–1690: King William's War (The Northern Border Slaughters)

• Ancestral Intersection: On March 18, 1690, a French-Abenaki force executes the Salmon Falls Massacre (Berwick, Maine). Timber mill pioneer Nathan Lord I is caught in the assault and dies during the chaotic wartime evacuation of the settlement.

1692: Frontier Captivity

• Ancestral Intersection: Moses Littlefield is captured by French forces during a brutal border raid on Wells, Maine. He is marched to Quebec as a prisoner of war and interrogated due to his family's surveying knowledge of English frontier defenses. His infant daughter, the future centenarian Martha Littlefield, survives the raid inside a fortified garrison house.

🪵 Colonial America & The First Great Awakening (1701–1763)

1704: The Deerfield Massacre (February 29)

• Ancestral Intersection: Both branches of the Catlin line collide with history on this bloody winter night in western Massachusetts. John Catlin III is killed inside the burning palisade defending the garrison houses. His brother, Joseph Catlin (ancestor of the western artist George Catlin), is killed simultaneously in the meadow counter-attack.

1707: Queen Anne's War

• Ancestral Intersection: Moses Littlefield is killed in action during a border skirmish near Wells, Maine. His widow, Martha Lord, pulls her family back south to the safety of Dover, New Hampshire. It is here that her daughter, Martha Littlefield, marries Thomas Stevens.

1717: The Rebuilding of Pequotsepos Manor

• Ancestral Intersection: Following a catastrophic fire on the eve of his wedding, Daniel Denison rebuilds the family manor house in Stonington, Connecticut, thriftily recycling the charred, structural timbers of his grandfather Captain George Denison's original home into the new framework.

1730–1760: The First Great Awakening Sweeps the Colonies

• Ancestral Intersection: The religious revival fundamentally shifts the naming conventions of our tree. Adolphus Skinner Brown is named directly after prominent theological leaders of the Universalist movement sweeping upstate New York's "Burned-Over District."
• Ancestral Context: The Bailey and Plympton families transition into permanent agricultural dynastic lines, clearing multi-acre properties in central Massachusetts, Connecticut, and New York, funding the construction of early colonial meetinghouses.

1750s: The Post-War Reclamation of Maine

• Ancestral Intersection: Following the stabilization of the French frontier, Olive Stevens and her husband, master blacksmith John Catland (Catlin), migrate from New Hampshire back to the Maine coast, permanently re-occupying Boothbay and rebuilding the maritime economy with John’s industrial forge.

🦅 The American Revolution (1763–1783)

1765: The Stamp Act Sparks Outrage

1774: The Emergency Militia Acts

• Ancestral Intersection: Captain Caleb Hall is elected as a civic and military officer of the Kent County Militia in Rhode Island, enforcing mandatory weekly drills and securing interior supply corridors against British foraging parties launching from occupied Newport.

1775–1783: The Revolutionary War

• Ancestral Intersection: John Catland (1718–1808) serves in Colonel Obadiah Johnson’s Regiment and the 20th Connecticut Militia. Operating his heavy blacksmith forge to manufacture grapeshot and repair weaponry, John continues to march on emergency coastal alarms well into his sixties.
• Ancestral Intersection: John Gardner (1753–1837) enlists out of Exeter, Rhode Island. He fights under Captain Bates at the grueling Battle of Rhode Island (August 29, 1778), standing his ground at Quaker Hill during a critical rear-guard action that prevents the annihilation of the retreating American army.
• The Minutemen Mobilization: Members of our Pierce and Plympton lines march directly on the alarms of April 19, 1775, answering the call at Lexington and Concord as part of the Middlesex County militia networks.
• The Wadsworth Brigade Reinforcements: In June 1776, our 6th great-grandfather, Oliver Bailey (1738–1822), enlists as a Private in the 8th Company under Capt. Cornelius Higgins (Col. William Douglas' 5th Battalion, General Wadsworth's Brigade). Raised to reinforce George Washington’s desperate defense of New York, Oliver stands on the front lines at the brutal Battles of Long Island and White Plains.
• The Continental Line Vanguard: From 1776 to 1778, our 5th great-grandfather, Zephaniah Rogers (1747–1823), serves on the Continental Line in Colonel Elmore's Regiment (Capt. William Satterlee's Company and later Capt. Daniel Davis's Company), marching through the critical tactical shifts of the mid-Atlantic theater.

1777–1778: The Continental Army at Valley Forge

• Ancestral Intersection: Our cousin, 13-year-old Putnam Catlin (father of the artist George Catlin), serves as a frontline tactical drummer boy for the 2nd Connecticut Regiment, beating cadences through the freezing mud of Valley Forge and the 100-degree heat of the Battle of Monmouth.

1781: The Battle of Johnstown

• Ancestral Intersection: Young Solomon Brown (1765–1839), our 4th great-grandfather, enlists as a private and camp musician in Colonel Marinus Willett's New York Levies. He tracks Loyalist raiders through the trackless northern forests and beats tactical signals at the fierce Battle of Johnstown just days after Yorktown falls.

🏛️ The New Nation & Federalist Era (1783–1800)

1785: Legacy of the Eagle & The Society of the Cincinnati

• Ancestral Intersection: On December 4, 1785, Surgeon Caleb Sweet, Esquire, MD, our 5th great-grandfather, is formally admitted to the highly exclusive Society of the Cincinnati. He is awarded the prestigious Order of the Cincinnati medal—a bronze badge in the shape of an eagle bearing the image of Cincinnatus. Signed off under the legacy of the Society's first President General, George Washington, this honor cements Dr. Sweet’s status as a literal founding father of the new Republic.

1787: The Architecture of the Republic (The Constitutional Convention)

• Ancestral Intersection: As the U.S. Constitution is hammered out in Philadelphia, our family is operating at the absolute pinnacle of statecraft. Our cousin Roger Sherman (1721–1793) cements his place in immortality as the architect of the Great Compromise and the only person to sign all four foundational papers of the United States: the Continental Association, the Declaration of Independence, the Articles of Confederation, and the U.S. Constitution.
• Ancestral Intersection: Standing shoulder-to-shoulder with Sherman is our cousin Oliver Ellsworth (1745–1807). A towering, underrated Founding Father, Ellsworth helps draft the Constitution, names the "United States," and later authors the Judiciary Act of 1789 before serving as the nation's third Chief Justice.
• Ancestral Intersection: On December 30, 1787, Solomon Brown marries Mary Sweet in Saratoga County, New York. Decades later, Mary will cut these exact marriage and birth record pages directly out of the family Bible to send to the National Archives as unassailable proof of their frontline Revolutionary alliance.

1789–1800: Standing at Washington's Right Hand

• Ancestral Intersection: Living to the astronomical age of 101, Martha Littlefield-Stevens (c. 1691–1792) witnesses Washington take office. Her single lifespan bridges the raw, isolated 17th-century world of Indian garrison warfare straight into the constitutional dawn of the United States.
• The Engine of the State: Our 6th great-granduncle, Colonel Timothy Pickering Jr. (1745–1829), serves at the absolute epicenter of early American power. One of the most brilliant, combative, and unyielding figures of the Federalist era, Pickering operates as George Washington’s adjutant general during the war, and later enters his cabinet as Postmaster General, Secretary of War, and Secretary of State (1795), continuing as Secretary of State under John Adams into 1800.

1796: The Birth of an Artistic Legacy

• Ancestral Intersection: Our cousin George Catlin (1796–1872) is born to the Revolutionary drummer boy Putnam Catlin. Raised on his father’s war stories and ancestral memories of the Deerfield Raid, George dedicates his life to painting and preserving the vanishing leadership and history of the Indigenous nations of the American West.

🐎 Tensions & The War of 1812 (1808–1815)

1812: The Frontier Mobilization

• Ancestral Intersection: Inheriting his father Solomon’s early military maturity, 14-year-old Samuel R. Brown (1798–1877), our 3rd great-grandfather, enlists as a Private in Lieutenant Colonel James V. Ball's Squadron of Light Dragoons. He serves as an elite, mounted courier and scout under General Harrison, enduring the brutal, freezing swamp campaigns of the North Western Army.
• Ancestral Intersection: Simon Weeks enlists as a Private under Lieutenant Colonel Christopher P. Bellinger, taking up arms along the high-stakes Sackets Harbor and Ogdensburg corridors to block British amphibious invasions launching from Canada along the St. Lawrence River.
• Ancestral Intersection: John Taylor Barstow mobilizes for frontier duty, serving on the New York border lines. His daughter, Polly Barstow, will later marry James Catland, structurally bonding the Denison, Barstow, and Catland lineages.
• A Hero of Two Wars: Having survived the freezing trenches of the Revolution, an aging Oliver Bailey (1738–1822) steps forward yet again during the War of 1812, cementing his legendary status in family lore as a resilient, multi-generational defender of American sovereignty.

1813: Fort Stanwix & The Road to Ohio

• Ancestral Intersection: Following his strategic deployments at places like Fort Stanwix, Zephaniah Rogers and his children help pave the great westward migration paths. This generation transforms our family from New England coastal settlers into the pioneering vanguard that settles the wild, rich valleys of Ohio.

1815: The Aftermath and the Jefferson County Convergence

• Ancestral Intersection: With the northern border permanently secured, the veterans migrate. Samuel R. Brown sells his 160 acres of federal Western Bounty Land scrip to speculators, converting raw frontier land into immediate cash. He uses this capital to buy out the heirs of his father-in-law Simon Weeks, consolidating a massive, independent agricultural homestead in Philadelphia, Jefferson County, New York—setting the stage for his own sons to march forward into the American Civil War.

📚 Deep Dives into Our Ancestral Archive

To explore the full, long-form narratives behind these timeline intersections, check out our dedicated family profiles:

• The Architects of the Republic: Cousin Roger Sherman and the Sherman Spirit
• America 250, Caleb Sweet: An Original Member of the Society of the Cincinnati
• The Thirty Coats: The Forging of Haddam, Connecticut
• Fort Stanwix, Zephaniah Rogers and the Road to Ohio
• Oliver Bailey (1738-1822) — A Hero of Two Wars
• The Engine of the State: The Uncompromising Hand of Timothy Pickering
• Our New Netherland Dutch & President Martin Van Buren
• America 250, Oliver Ellsworth: A Most Underrated Founding Father
• As American as French Apple Pie

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