This article appeared in a series of articles pertaining to the early history of twenty two families of Westchester County, New York. They were published during the summer and fall of 1951 as part of a special feature in the Westchester Group Newspapers and Affiliates. The author was Maureen McKernan. The article on the Oakley family was the 3rd of the series.
Of Miles Oakley, founder of the Oakley family in Westchester, little is known except he was born in England, was in Great Neck, in 1669 and died in November, 1682, on a farm in that part of old Westchester which is now the Westchester Square neighborhood of the Bronx.
West Chester town became an incorporated borough in 1675 and Miles Oakley was elected the first Mayor. His tombstone in St. Peters graveyard near Westchester Square bears engravings saying that Miles Oakley was born in Oakley Grove, parish of Oakley, England, July, 1645. It is thought by historians that he may have been of a family that had been too closely associated with the reformer, Oliver Cromwell, and so turned toward the New World, as did many other Roundheads, after the fall of Cromwell's Commonwealth and the Restoration of the Crown of Britain.
Man Of Importance
At any rate, Miles Oakley's choice as first Mayor of West Chester attests to his powers of leadership and his son, Mile 2d, born in old West Chester in 1671, was a man of such importance that he was a member of the Common Council in 1696 and a vestryman of St. Peter's Church in 1709. He was an Alderman in 1719, President of the Board of Town Trustees in 1720, and Mayor in 1730-32. His wife was Elizabeth Barlow, of another important founding family.
Thomas Edward Oakley, Mount Vernon merchant and historian of today, is the eighth generation from Miles Oakley and the 34 Oakley families families currently living throughout the county are but a few of the families here that can trace their ancestry directly to Miles Oakley of West Chester. Grenville MacKenzie, the historian, lists more than 100 Oakley families in Westchester, Long Island and New Jersey alone.
First of Eastchester Oakleys
Joseph Oakley, fourth generation and descendant of three generations of Miles Oakleys of West Chester, 1726-97, followed the trend of his generation and moved to what is now Yonkers, just west of Mile Square, to become a lease holder in Philipse Manor. Joseph died on his farm when he was seventy-five. His son, Thomas, great-great-grandfather of Thomas Oakley of today was founder of the "Eastchester Oakleys" and a patriot during the Revolutionary War.
A member of this branch of the clan, Isaac Oakley, owned the Oakley Tavern in White Plains, where so much history was made when it was the patriots' gathering place during the Revolution. Cornelius and Isaac Oakley were trusted guides for Gen. Washington during the Westchester campaigns.
Three generations of Isaac Oakleys ran the tavern before it burned in 1868, the first Isaac owning a 122 acre farm on North Street, part of which comprises the grounds of the Westchester division of the New York Hospital. This Isaac and his wife, Sarah Haviland of the Rye family, are buried in the Friends' Cemetery in Harrison.
By 1716 many Oakleys had pushed into Cortlandt. Fifteen graves and vaults of Oakleys are identified in St. Paul's Church, Eastchester, and many more are known to be buried there though their graves are lost.
Marries a Van Tassel
By 1790 Oakleys had moved on into Ulster County, one of them taking a Van Tassel girl of Tarrytown as his bride.
Thomas, the first who was born on his father's farm in Yonkers bought a farm in Eastchester in 1785 and he died there in 1825. He was a leader in politics and after fighting with the American Army during the Revolution he served Eastchester variously as Overseer of the Poor, Highway Superintendent Commissioner or Justice of the Peace. His farm ran from the White Plains Post Road, West Lincoln Ave. to the Bronx River Parkway, in what is now Fleetwood. His farmhouse stood at the corner of West Lincoln Avenue and North Seventh Avenues. The playground of the Nicholas Junior High School in Mount Vernon was once the Oakley pickle patch.
The son of this Thomas, also named Thomas, grandfather of Mount Vernon's respected and revered Thomas Oakley of today, was born July 4, 1783, and died in 1852. He helped guard Westchester's shoreline along the Sound from British attack during the War of 1812 as a member of Capt. Bishop Underhill's company. He served as Town Assessor, Overseer of the Poor and Superintendent of Highways.
Last Mate of Line
Thomas Edward Oakley is the last male of his line, his only child being his daughter Leslie, wife of Arthur J. Beyer of Falls Church, Va. The family name remains alive and numerous through other branches.
Mr. Oakley has for years been a corner stone of the Mount Vernon Rotary Club and history is his avocation. For 12 years he has been working on the Eastchester town records, having them complete from 1664 to 1860. Mount Vernon was in Eastchester until it became a city. Just now he is studying old newspaper files of the 1850s for historical items about Eastchester and Mount Vernon. He has just completed the study of the Hudson River Chronicle 1837-1850. He is a trustee for Mount Vernon of the Westchester Historical Society.
| Hunt | Seacord | Oakley | Tompkins | Purdy | Haviland | Odell |
| Hatfield | Gedney | Acker | Horton | Van Wart | Van Tassel | Storm |
| Lent | Sutton | Hoyt | Hays | Hyatt | Coles | Griffen |
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