The Wheeler-Dealer: Samuel Howe

Samuel How(e) 1642-1713

Samuel How(e) lived lives enough for several people in his seventy years. He was a carpenter, a soldier, a politician, father of thirteen children, a tavern keeper, and above all a wheeler-dealer. Not that it would have mattered a bit to Samuel, but he was also my 7 x Great Grandfather.

It is hard to rein in Samuel’s stories and concentrate on one aspect of his life. I find it pretty impressive that he was the second new world tavern keeper in the How family when you consider that he was born just twenty-two years after the Mayflower landing and only four or five years after his own father arrived on the continent.

When I wrote about his son, David How, I said that Samuel How was the Donald Trump of Colonial Sudbury. I did not mean by that he was a millionaire–or even the Massachusetts frontier equivalent of a millionaire–however he was a man who played all the angles, made friends in all the right places, and constantly finagled himself a good deal. [UPDATE: When I wrote this, the world did not know Donald Trump in the same way they do since his run for the Republican nomination for President.  I regret comparing Samuel to Donald. While Samuel had activities–development, building, money-making, political–in common, he certainly did not share a similar value system.]

His acquisition of land started early.  Although he had been born in Sudbury, his father John How had moved the family to the new community of Marlborough in 1656, when Samuel Howe was a young teen.


The property, where Samuel built their home, now lies on the edge of the present town of Wayland, about six miles southeast of the Wayside Inn property developed by Samuel’s son David.

In their early married life, they had six children (between 1664 and 1674) and Samuel supported his family by working as a carpenter.  From the very beginning, he seems to have been adept at getting “government contracts.”

He lived near the Sudbury River that split the community and speculated that a cart bridge would be well used and appreciated, so he built the bridge.  The community, while welcoming the bridge, could not pay him for his work, however, they permitted him to collect a toll.  Before long, he was not only collecting toll for using the bridge but also charging the community for using the meadow that was accessed by the bridge.

This was in the 1670’s and the Indian wars were raging.  In April, 1676 the disastrous Sudbury fight, part of King Philip’s War (led by a dissident Indian known as King Philip) challenged Samuel’s spirit.  His brother John, Jr. was killed in the battle, and Samuel’s own house and barn were burnt to the ground.

Samuel Howe not only immediately rebuilt, but he took advantage of the situation to make one of his real estate deals.  Soldiers who had fought in the Indian wars were rewarded with grants of land in western Sudbury. When one of those soldiers died, Samuel arranged to buy Lot #50 from the family.

Only four years after the Sudbury fight, which changed his life significantly, he had to face the death of his wife Martha. The same year, 1680, his father died and left him another 25 acres of land.  Samuel never seemed slowed down by bad luck. The town gave him a contract to build stocks in front of the Meeting House, and the next year assigned him to be a “tithingman”, assessing others for real estate taxes. But it was the land deal he made with the local Indians in 1682 that made me begin to think of him as a Wheeler-Dealer.

Samuel How and his friend Samuel Gookin, negotiated a deal with the Natick Indians (a tribe of Alqonquin-speaking Christianized Indians who did not join “King Philip”). The  history of these ‘praying Indians’ is unique and fascinating.

Natick Indians

“John Eliot Speaks to the Natick Indians” by Hollis Holbrook
Natick, Massachusetts Post Office
Image by Thomas Portue.

Although Samuel’s father, John How had a reputation for treating Indians compassionately and being loved by them for his fairness, Samuel apparently saw them as another target for his enrichment.

The contract with the Indians specified the purchase of “200 acres more or less” and carefully defined the northern, southern and eastern boundaries of the land.  You will notice that there was no definition of the western boundary–which left How and Gookin with a grand opening to make a killing selling land to settlers flocking west to Sudbury.

Busily taking on more contracts to build things for the community, and no doubt building houses and glazing windows (another of his skills), Samuel found a new bride.  In 1685 he married widow Sarah Leavitt who was seventeen years younger than Samuel. From the late 1980s through the nineties, Sarah and Samuel had seven more children–the last born when Samuel was fifty-eight.

Obviously not a man to slow down, the year after he married Sarah, he tried to win a bid to build a new meeting house for the town. He failed to get the bid, but the selectmen later chose him to inspect the work.  Perhaps as a consolation prize, he was elected as one of seven selectmen in 1691, and served three more terms after the first one. The year after he became a selectment, his fellow town leaders showed their faith in him by recommending that he start a public house, so he followed in his father’s footsteps and sold drinks from his home.

Meanwhile, the Natick Indians realized that the deal they had made with How and Gookin was worse than one-sided.  In 1695 they hired a lawyer and took the two men to court, charging them with making a fraudulent deal and “encroaching” on Natick land they had no rights to.

The two men tried to defend themselves by explaining how much money they had laid out, in addition to taking on the care of some “squaws”. The judge agreed that they had encroached on land that belonged to the Indians, and returned 1000 acres to the Natick. That sounds like a good deal, until you read that left How and Gookin with 1700 acres–not a bad return on an investment in “200 acres more or less.”

It would not have been easy to sell land at the moment anyway, since Indian attacks continued to increase, and Samuel was listed between 1695 and 1697 as a Lieutenant in the Sudbury Militia. Ultimately, he was wounded in battle. (His brother Joseph served in the Marlborough Militia around the same time, and his brother Thomas rose to the office of Colonel.  Thomas was also later to keep a public house.)

In 1702/03, as we have seen, Samuel gave his son, David, land and helped him build a house for his new bride.  Samuel continued to renew his license to sell spirits each year until 1712.  He died in 1713, perhaps suddenly, because he left no will.  Or perhaps, with his record, he did not quite trust the contracts written by lawyers.


Samuel How's Gravestone.

Samuel How’s Gravestone. Picture taken by Charles Waid

How I am Related

  • Hattie Morgan (Stout), the daughter of
  • Mary Bassett (Morgan),the daughter of
  • Elizabeth Stone (Bassett) the daughter of
  • Elizabeth Howe (Stone), the daughter of
  • Israel Howe, the son of
  • David How, the son of Samuel How.

Notes on Research

  • In Public Houses: Drink and the Revolution of Authority in Colonial Massachusetts by David W. Conroy, (1995)
  • A History of Longfellow’s Wayside Inn by Brian E. Plumb (2011)
  • Middlesex County records found on Birth, death and marriage.
  • The tombstone picture came from Find a Grave, because although I visited the Sudbury Old North Cemetery, (located in Wayland MA) where Samuel is buried, I was unable to spot his grave.
  • I also have had assistance from the archivist and a historian at Longfellow’s Wayside Inn and the historian with the Sudbury Historical Society.


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1 thought on “The Wheeler-Dealer: Samuel Howe

  1. Bob Zeh

    I have done my searching on ancestry and I also did 111 Y Dna markers to find the root of my biological tree to Be Abraham Howe of Broad Oak Essex England. However since I was adopted I never knew any of this till I was 64. I actually find that being from and conceived in Port Huron Michigan that some darn Howe made it to Ireland perhaps Before Mervym Howe Fermanagh In the early 1700s and not the route where Abraham comes to Sudbury in 1636. I of course can not find this Early HOWE due to records being burnt in Dublin for Irish History, Some howe Perhaps earlier than his father Robert had a son that went to Ireland. A how with Y dNA testing would confirm this.


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