About the Author: Greg Cunningham

Greg Cunningham spent the greatest moments of his life in Chicago, IL.  He was born and 6 months later he moved.  See I have a good sense of humor.  Yes that was the first of over 20 moves.  When my dad took a promotion it was not in the same building, but in a different state.  My life and job’s have also taken me up and down the east coast. 

I started life February 21, 1966 in Chicago, IL and then moved to Cincinnati, OH, Pittsfield, MA, Newark, DE, Schenectady, NY, North and South Daytona Beach, FL, St. Cloud, FL, Jacksonville, FL, Gainesville, FL (BA at the University of Florida), Alexandria, VA, Woodbridge, VA, Fredericksburg, VA, Locust Grove, VA, Winchester, VA and as of today I live in Capon Bridge, WV with my beautiful wife Trisha Ann (Brooks) Cunningham.  We celebrated our 1st year wedding anniversary April 23, 2010 (been together for 3), and she makes everyday worth waking up to.  I work for the dreaded over paid federal government, and I got the genealogy bug from my father (Robert Lee Cunningham).  Google my name on the internet and you will see many Cunningham stories including The Life of Rear Admiral Winfield Scott Cunningham, published in 3 installments by Sea Classics, Corporal Michael Hayes Branninger Cunningham of the 18th Wisconsin Volunteers, published in America’s Civil War and American Apostles John Cunningham and Henry Harrison Deam.  All three were recently published in three issues of the Wisconsin State Genealogical Society’s newsletter.  Many of my ancestors (my wife too) came from Wisconsin. 

Thirteen American generations of the Wakelee/Wakeleys started with James Wakelee of Hartford, and Wethersfield, CT.  Stratford and Trumbull, CT were also home to 6 generations of Wakelees including David Wakelee, an Ensign of the Ninth Company of the Alarm List, 4th Regiment of the State of CT.  He received his commission in 1778 from Captain General Jonathan Trumbull.  I’m a member of the Sons of the American Revolution from my being descendant from David Wakelee.  David Wakelee was also a Sergeant in the Fourth Company, 2nd Regiment under Colonel Nathan Whiting in 1762.  I recently became inducted into the Sons of the American Colonists.  Ebenezer Wakeley, Jr. (Private in the First CT Light Artillery, wounded at Chester Station, VA), would be the first generation to move West.  He moved to Chicago, IL after the Civil War.  My first Wakeley story was Ebenezer Wakeley’s eyewitness account of the Great Chicago Fire of 1871, published in the newsletter of the Genealogical Society of Chicago.  His son Ebenezer Stone Wakeley, would have a son named, Ryland Stone Wakeley, who would in turn raise my wonderful mother Marilynn Viola Wakeley.  I hope you enjoy my newest attempt at trying to tell a story from the cobwebs left over by 13 generations of Wakeleys.  God Bless.


  1. Kelly says

    I have not met your mother Marilynn, but have heard stories regarding the life of Ryland Stone Wakeley Sr, and the very short life of Clyde Wakeley. Very sad.

  2. Celinda says

    Dear “Cousin” Greg,
    While researching, I came across your fantastic article regarding my 6th Great Grandfatther James Wakelee! I am overjoyed to see footnotes too! Thank you thank you thank you! I am related through his son Ebenezer,(1717-1800). I have a photograph of a deed from James to his son Ebenezer dated 1738, recorded in the Waterbury Land Records. Please contact me if you would like a copy of the photo. epacker120@aol.com

  3. Greg Cunningham says

    Kelly, Are we related? If you know my mother’s father, and her younger brother Clyde please email me. Thanks.

  4. kl says

    Celinda, I saw your post and wanted to follow-up.
    The founding American Wakelee, James Wakelee, was born around 1600 and died by 1690 in Rhode Island. Only know sons, according to geneologist Donald Jacabus were Henry Wakelee born about 1620 and died July 11, 1689, and possibly a Richard Wakelee, born by 1632 (went by name Walkley), and died August 6, 1681.
    In your post you mention “I am related through his son, Ebenezer (1717-1800).” You must have meant “great great grandson.” You are my blood cousin through Henry Wakelee and Sarah Burts son, James Wakelee (grandson of American founder, born 1653, died about 1729) and Hannah Chauncey (born 1670, died 1699). Their son James Wakelee (great grandson of American founder, born December 28, 1688, died May 4, 1762), married Sarah Shelton (born 1694/1695, died April 1745). Their son Ebenezer Wakelee (great great granson of American founder, born January 13, 1716/17, died January 1800 at Wolcott) married Elizabeth Nichols (born 1717, died August 11, 1802).
    Our Wakelee line is from Henry and Sarah (Burt) Wakelee’s son Jacob Wakelee (born 1653, and died December 20, 1726/27). Because of the same birth year, our Jacob most likely is a twin of your James!!
    Many years ago I received alot of information about your family from a George Cole (gec1948@hotmail.com). I’m not sure if this email is still working or not, but he had alot of information on Ebenezer and Elizabeth (Nichols) Wakelee’s children Elizabeth, Hannah (1st), Hannah (2nd), David, and Sarah.
    I have put together a 350 page collection of all the direct Wakelee descendants (13 generations). If you give me your snail address I will place the book on a CD and mail it to you. Hopefully, you will then send me updates and/or corrections so I can make the Wakelee Archive as complete as possible.
    You can go to the Bridgeport CT Public Library, History Center, and see a portion of my great-great grandfather’s diary. He is also an Ebenezer Wakeley, but with the modern spelling.
    My address is 9 Beck Gap Road, Box 556, Capon Bridge, WV 26711. I would love to see a copy of the deed from your James to Ebenezer dated 1738. I will keep it with all my other Wakelee records.

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