Olive Watts Kelly: My Mom’s History at 100 Years- Plymouth to Long Island over 15 Generations

It’s hard to believe that so much American history could run through one person. 

My mom, Olive Watts Swanson Kelly, is 100 years young. She was born in her parents’ Lake Grove home in 1922. The house was built in 1799 and served as the first schoolhouse in the Ronkonkoma-Lake Grove area for Sachem schools.

The Hawkins Avenue home still stands today facing Smith Road. Olive had an older brother named Vernon and a twin brother Oliver. She married twice. Olive has two sons, Ralph and Harry, four grandchildren and six great-grandchildren.

She lived through and witnessed many era’s including: horse drawn buggies, Ford model T’s, outhouses, oil lamps, ice boxes, nightly radio programs, gas-fired lighting, coal-burning heat, installation of in-door plumbing and electric wiring, refrigerators, various appliances, lightbulbs, black and white television, telephones, computers, color television, records, Internet, etcetera.

Then, there’s World War I recovery and the impact of the Great Depression, World War II, Korean War, and Vietnam. Then consider all the extreme weather, severe blizzards, the 1939 Hurricane and much, much more.

She lived through the good times and bad– saw many marriages, births and deaths. 

Olive’s father, Harry Watts, emigrated to the U.S. through Ellis Island from Ireland in 1912. Her mother, Pearl Smith Watts, had an incredible family ancestry dating back to the Mayflower, which included Elder William Brewster, Richard Warren, Isaac Allerton, John Alden, William Bradford, Edward Doty, Henry Sampson and Myles Standish.

If living through those past 10 decades wasn’t enough, then it’s her 400-year American ancestry that makes you sit back and marvel. It all started with her Overton and Smith maternal grandparents.

All Olive’s ancestors were involved in the search, the journey and the building of Plymouth, Massachusetts Bay, Massachusetts, New Haven, New London, Connecticut and Eastern Long Island settlements. They include many of the earliest founders of all 10 Long Island towns, starting with Southampton and Southold.

Find a brief summary below: (Note: Keep in mind that if your Long Island ancestry dates back far enough, it seems that you will have common ancestry with almost everyone)

You could start with the Mayflower. The Mayflower arrived in Plymouth in 1620. Elder

William Brewster was their religious leader and assisted in organizing the voyage and

Plymouth settlement. It was believed to be Brewster who suggested the settlers observe

several days of worship and Thanksgiving for all provided and their safety. This event

is recognized as America’s first Thanksgiving since it was not done by order from England, but of true appreciation.

Elder Brewster also played a major role as the primary author of the Mayflower Compact– which would become America’s first charter of Freedom, thus serving as the underpinning of the future Declaration of Independence and the U.S. Constitution.

Of the 13 original English colonies, Olive’s ancestors were involved in the formation and planning of Virginia, Massachusetts, Connecticut and New York.

Then there’s the Captain Kidd story. Captain Jacob Conklin, one of Olive’s ancestors, actually sailed with Kidd. Conklin also built the first home in Babylon Town.

There was a pirate named Joseph Bradish who was much more fierce than Kidd. Bradish nearly caused one of Olive’s ancestors, Col. Henry Pierson (Person) to the gallows for harboring him.

By marriage, Olive’s ancestry also includes John Underhill, the famous military commander who dealt a strong hand then dealt with the Native Indians. The town of Southold hired him to assure peace. Per his reputation, they never experienced a single issue.

Many historical locations throughout Long Island, Connecticut and Plymouth, Massachusetts tie back to Olive’s early ancestors, such as: Plymouth Plantation, Mayflower / Plymouth Rock in Massachusetts, Founders Landing and Thomas Moore House in Southold, George Washington Spy tours in Setauket, Thompson House and Brewster House in Setauket, William Floyd Estate in Mastic, Epenetus Smith Tavern in Smithtown, St. James General store in St. James, David Conklin Farm House in Huntington, and the Hallock Museum in Riverhead– to mention a few.

Many of the first structures and churches on Long Island belonged to Olive’s ancestors, including Rev. John Young’s First Presbyterian Church of Southold and Rev. Nathanial Brewster’s flock that met in his home in Setauket.

They also entertained Presidents such as then-General Ulysses S. Grant at Nathanial Conklin’s homestead and George Washington at various homes of ancestors in Oyster Bay, Smithtown, Hauppauge and Brookhaven. Many were from Setauket such as Abraham Woodhull, Caleb Brewster and Anna Strong.

Col. William Floyd is also included. Floyd was a signer of the Declaration of Independence. Floyd’s great-grandfather is Richard Bull Smith, who is also an ancestor.

Even President Abraham Lincoln, signer of the executive-ordered Emancipation Proclamation, 13th Amendment pioneer and deliverer of the Gettysburg Address is found to be included by way of Richard Bull Smith ancestry.

Olive’s ancestors fought in all the major wars including: the Pequote Indian War, French and Indian War, the Civil War, the American Revolution, the War of 1812, WWI, WWII , the Korean War and Vietnam. 

They were also deeply involved in George Washington’s Setauket Spy Ring. Her ancestors were founding members and families from all towns located in what is today’s Suffolk and Nassau Counties, along with Jamaica and the eastern side of what is Queens today.

LONG ISLAND HISTORY, EXPANDED

South Hampton

In 1635 Richard Smith, Edward Howell, Richard Woodhull and Thomas Halsey arrived on board the New England-bound ship ‘John” from England. In 1640, they moved to Hempstead but had to flee to South Hampton due to threats from the Dutch. Early South Hampton settlers include names like Howell, Halsey, Sayre and Terry—all ancestors.

Southold

In 1640, Rev. John Young arrived in Southold from New Haven along with William Wells, Reeves, Tuthill, Brush, Clark, Conklin, Cooper, Elton, Hallock, Horton, Moore, Norton, Overton,

Purrier, Salmon, Terry and Vail—all ancestors.

Brookhaven

The first structure built in the town in 1665 was for Rev. Nathanial Brewster. Other founding settlers in the 1700: John Thompson, Col. Richard Woodhull and Col. Richard Floyd—all ancestors.

East Hampton

In 1640, nine Puritans from Lynn, Massachusetts landed in Southampton who would later move to East Hampton. Some of whom include Thomas Moore, Baker, Miller, Conklin and Thompson—ancestors.

Shelter Island and Robbins Island

In 1642, the Islands were purchased by Stephen Goodyear. In 1710, ten owners from Southold formed the new town. They include Havens, Vail, Conklin, Tuthill and Hopkin—all ancestors.

Smithtown

The founder of the town is Richard Bull Smith. As the story goes, he rode his bull named Whisper around the area that defined the town border. Another ancestor.

Huntington

In 1656, the town founders included Jonas Wood, Thomas Wickes, Conklins, and Brush—ancestors.

Riverhead

The town’s first land owner was William Wells. The first development for trade was established by Joshua Horton. The first settlers were the Hallocks. Both are ancestors.

Islip

Benjamin Nichols was the town’s first Supervisor. His father is known as the father of the Town of Islip. Ancestor.

Oyster Bay

Elizabeth Feake was one of the earliest town settlers. She married Henry Winthrop, the son of Governor John Winthrop. Other early settlers include the Wrights, Ludlum, Weeks, Rogers,

and Cooper. Ancestors.

Hempstead

In 1643, Rev. Robert Fordham led the effort to begin a settlement in the town. Other direct lineal ancestors of the earliest founders are Matthew Mitchell, Christian Forster, and Jonas Woods. Other related owners include Jackson, Ward, Smith, Pierson, Rogers, Lines and by marriage, John Underhill. Ancestors.

Jamaica

We are related to three of the 14 original citizens that founded the area of Jamaica. They are Robert Jackson, Andrew Messenger and Roger Lines. Ancestors.

New Haven

Many of Olive’s ancestors had first arrived at New Haven Colony and then moved onto Long Island.

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