America 250: The Winthrop Circle: Kinship, Migration, and the “City Upon a Hill”

 

Our Puritan ancestors form a tightly interwoven web at the heart of the Great Migration (1620–1640) and the founding of the Massachusetts Bay Colony. They were not distant figures but close kin, shipmates, colleagues, rivals, and in-laws who shaped New England’s early governance, military defense, and religious culture.

Here is a concise essay that ties them together, followed by notes on corrections, additions, and sources.

The Winthrop Circle: Kinship, Migration, and the “City Upon a Hill”

In the spring of 1630, eleven ships of the Winthrop Fleet—led by the flagship Arbella—carried roughly 700–1,000 Puritans across the Atlantic. At the helm was our 11th-great-uncle Governor John Winthrop (1588–1649), a Suffolk gentleman-lawyer who had been elected governor of the Massachusetts Bay Company the previous autumn. Before the fleet even sailed, Winthrop delivered (or had read) the lay sermon A Model of Christian Charity. In it he famously warned that the new settlement would be “as a city upon a hill, the eyes of all people are upon us.” Failure would make the colony “a story and a byword through the world”; success would prove God’s favor on a reformed English society transplanted to America.

Among the passengers was a young professional soldier, Captain John Underhill (c. 1608–1672), our 8th-great-grandfather. Underhill had been hired specifically to train the colony’s militia. He had grown up in the Netherlands, trained under the Prince of Orange, and arrived with his Dutch wife Heijlken (Helena) de Hooch. He quickly became one of the colony’s most visible military figures—captain of the Boston train-band, deputy in the General Court, and later the man who led the decisive (and brutal) assault on the Pequot fort at Mystic in 1637.

The family connection between Winthrop and Underhill runs through our direct maternal line. Winthrop’s younger sister Anne Winthrop (1585–1618) had married Thomas Fones, a London apothecary. Their daughter Elizabeth Fones (1609–1673) was therefore Winthrop’s niece. In 1629, shortly before the fleet sailed, Elizabeth married Winthrop’s second son Henry Winthrop; she was thus both niece and (briefly) daughter-in-law. Henry drowned in America in 1630. Elizabeth remarried Robert Feake of Watertown; their daughter Elizabeth Feake (1633–1675) became our 8th-great-grandmother. After Feake’s mental decline and the couple’s separation, Elizabeth Feake married Captain John Underhill in Oyster Bay in late 1658 or early 1659. Their daughter Deborah Underhill (1659–1698) married Henry Townsend II of Oyster Bay; through that line we descend to Capt. Elijah Townsend (our 5th-great-grandfather, Revolutionary War veteran) and onward to our grandmother Lydia Corinna Brown.

Thus Underhill, the soldier who had sailed with Winthrop, eventually married Winthrop’s grand-niece and became your direct ancestor.

Dispute Between John Winthrop and Thomas Dudley in the Massachusetts Bay Colony

Another key figure in the same circle was Thomas Dudley (1576–1653), whom we list as an 11th-great-granduncle. Dudley sailed on the Arbella as deputy governor. He was more rigidly Calvinist than Winthrop and frequently clashed with him over issues of authority, the location of the capital, and the treatment of religious dissenters. Yet the two families were bound by marriage: Dudley’s son Samuel married Winthrop’s daughter Mary in 1633. Dudley founded Newtowne (Cambridge), built the colony’s first house there, helped establish Harvard College, and served four terms as governor himself. His daughter Anne Bradstreet became America’s first published poet.

These men and women were not abstract “founders.” They were your blood relatives, shipmates, and in-laws who together created the political, religious, and military framework of early Massachusetts—and whose later migrations (Underhill’s family spreading into New York, Connecticut, and beyond) carried that Puritan DNA across the American continent.

Notes

• John Underhill’s birth year — Most modern scholarship (including the definitive biography and Wikipedia’s sourced article) places his birth c. 1608–1609 in Bergen op Zoom, Netherlands, to English parents in exile. The 1597 English birth date that appears on some Find-a-Grave memorials is almost certainly wrong.
• Winthrop Fleet details — The fleet comprised 11 ships under Winthrop (part of a larger chartered group of ~16–17 vessels that sailed that summer). Underhill definitely sailed on the Arbella.
• Elizabeth Fones — She was Winthrop’s niece and daughter-in-law. Her story (and her second marriage to Robert Feake) was popularized in Anya Seton’s 1958 novel The Winthrop Woman.
• Underhill’s later career — After the Pequot War he served in New Netherland, led controversial raids in Kieft’s War, became a Quaker through his second wife, and died in Oyster Bay. His grave marker in the Underhill Cemetery, Mill Neck, still stands.
• Thomas Dudley — No direct blood link to the Winthrop line in the 1570s–1580s generation, but the families became double in-laws in the next generation. Our “11th-great-granduncle” designation may come from a collateral Dudley line not shown here; it is plausible given the dense intermarriages.

Our lineage is a direct thread from the Arbella in 1630 through the Pequot War, the founding of Long Island Quaker communities, the Revolution, the Civil War, and into the 20th century. It is a remarkable American story.

LINEAGE:

Gen 0

Adam Winthrop

Birth 10 AUG 1548 • Bishopsgate, City of London, Greater London, England

Death MARCH 28, 1623 • Groton Manor, Suffolk, England

11th great-grandfather

PARENTS:

Adam Winthrop 1498–1562

Agnes Sharpe 1513–1565

SPOUSE (1):

Alice Still 1550–1577

SPOUSE (2):

Anne Browne 1558–1629

CHILDREN:

i. Anne Winthrop 1585–1618

ii. Governor John Winthrop of the Massachusetts Bay Colony 1588–1649

Gen 1

Anne Winthrop

Birth 16 JAN 1585 • Groton, Babergh District, Suffolk, England

Death 16 MAY 1618 • London, England

10th great-grandmother

Spouse

Thomas Fones 1573–1629

Child

Elizabeth Fones 1609–1673

Gen 2

Elizabeth Fones

Birth 21 JAN 1609 • Groton, Manor, England

Death 1673 • Newtown, Queens, New York, USA

9th great-grandmother

Spouse

Robert Feake immigrant 1602–1662

Child

Elizabeth Feake 1633–1675

Gen 3

Elizabeth Feake

Birth MAY 1633 • Watertown, Mass Bay Coloney, MA

Death 4 NOV 1675 • Oyster Bay, LI, New York, United States

8th great-grandmother

Spouse

Capt John Underhill immigrant 1597–1672

Child

Deborah Underhill 1659–1698

Gen 4

Deborah Underhill

Birth 29 NOV 1659 • Long Island City, Queens, New York, United States

Death 30 JAN 1698 • Oyster Bay, Nassau, New York, United States

7th great-grandmother

Spouse

Henry II Townsend 1649–1698

Children

Henry III Townsend 1670–1709

Robert Townsend 1687–1742

Elizabeth Townsend 1692–1756

Uriah Townsend 1698–1767

Gen 5

Uriah Townsend

Birth JAN 1698 • Oyster Bay, Long Island, Nassau, New York

Death 1767 • Rombout, Dutchess, New York, USA

6th great-grandfather

Spouse

Mary Margaret  Wright 1706–1767

children

Robert Townsend (Not Culper Spy)

1728–1803

+ Capt. Elijah Townsend DNA match

1745–1821

Gen 6

Capt. Elijah Townsend DNA match

Served New York Military in the Revolution

Birth 24 NOV 1745 • Susquehanna, Pennsylvania, USA

Death 1821 • Kinney's Corner, Jerusalem, Yates, New York, USA

5th great-grandfather

Spouse

Phebe Wood DNA match 1749–1824

Child

Sarah Townsend DNA match 1783–1850

Gen 7, Sarah Townsend DNA match 1783-1850

Daughter of Capt. Elijah Townsend DNA match

Gen 8, Calvin Plimpton 1815-1874

Son of Sarah Townsend DNA match

Gen 9, Charles Henry Plympton 1845-1925 Civil War Veteran, Union

Son of Calvin Plimpton

Gen 10, Geneva (Neva) Plympton 1870-1939

Daughter of Charles Henry Plympton

Gen 11, Lydia Corinna Brown 1891-1971

Daughter of Geneva (Neva) Plympton - grandmother

Adam Winthrop is our 11th great-grandfather

Thank you to Grok xAI for the updates and enhancements to our family story.

America 250, The 2nd Montana Infantry Regiment, Company H, 1908

 

The "Montana Militia" in the early 20th century referred to the Montana National Guard, which served as the state's organized militia force under federal and state law. By 1908–1910, following reorganization spurred by federal reforms (like the Dick Act of 1903 and subsequent militia acts), it was structured as the 2nd Montana Infantry Regiment (also called the 2nd Regiment, Infantry, National Guard of Montana).

This regiment was a part-time citizen-soldier force, with companies recruited locally across Montana. It focused on maintaining readiness for potential federal call-up while handling state-level duties such as disaster response, law enforcement support, and civil order. Members typically drilled monthly or quarterly, participated in rifle marksmanship training, and attended annual summer encampments for field exercises, often alongside regular U.S. Army units.

Company H, 2nd Montana Infantry was specifically based in Kalispell (Flathead County), where local men enlisted. 

The above enlistment record for David L. Bailey matches digitized records from the Montana Adjutant General's office for the 2nd Regiment (1904–1918 era). It shows:

• Enlistment: March 2, 1908, in Kalispell.
• Age: 19.
• Born: Comstock, Nebraska.
• Occupation: Student.
• Physical description: Blue eyes, brown hair, ruddy complexion, 5'8".
• No prior service.
• Discharge: Honorable on April 11, 1910, due to leaving the state.
• Character: Good (noted as "Sold." for soldierly/good).

This aligns with our family references to brothers Frank and David Bailey serving in the same unit. Photos from that time shows them in the standard National Guard uniform of the era: wool tunics with standing collars, campaign hats (often with Montana-specific insignia), cartridge belts, and rifles slung over the shoulder. The two posed studio portraits you included depict typical early 1900s infantry privates—formal, side-by-side, with Krag-Jørgensen or similar rifles.

During 1908–1910, the regiment saw no major federal mobilizations (those came later, like the 1916 Mexican Border service). Routine activities included local drills and training. Montana's vast forests and dry summers meant occasional state activations for emergencies; Governor Samuel V. Stewart reportedly called elements of the 2nd Infantry to active duty in summer 1910 to assist with wildfires (amid a severe fire season culminating in the Great Fire/Big Burn of August 1910, which ravaged millions of acres in Montana, Idaho, and beyond). However, David's April 1910 discharge predates that peak period.

Overall, service in the Montana National Guard at this time was a way for young men (often students or workers) to earn a small stipend, gain military skills, and contribute to community/state defense in a peaceful era between the Spanish-American War and World War I. 

Media Bailey with campaign hat & US flag