Birth and Early Family History:
John Woodlief was listed 23 May 1609 in the 2nd Charter of the Virginia Company.  From this it has been assumed he was in Virginia in 1609, and then returned to England later bringing his family to Virginia. However, in 1609 John Woodlief was in England where he married on 1 May 1609 Steventon,Berkshire,England Mary Archard    The marriage controversy arises from an alternate marriage date for John Woodlief of Jan 5, 1609 at Steventon, Buckinghamshire, England for which there is no firm documentation. So, it is not clear if there were two different John Woodliefs both married in 1609. One at Steventon, Buckinghamshire and the other at Steventon, Berkshire. Today, the village of Steventon, Berkshire is in Oxfordshire thanks to a 1974 boundary change. Thus far no references have been found suggesting there is or ever was a village of Steventon in Buckinghamshire. However, there is another Steventon in Hampshire, famous as the birthplace of Jane Austen.
Life in Virginia and the First Thanksgiving:
The first mention of John Woodlief in Virginia was 1619 in the records of the Virginia Company.  Of course that does not mean that he wasn't in Virginia before but simply that the records from that era are scarce and he was not mentioned prior to 1619. John Woodlief's arrival in Virginia is well known. The ship, Margaret, left Bristol, England on 16 September 1619 with more than 40 settlers for Berkeley Hundred, a private colony along Virginia's James River. In 1618, Sir William Throckmorton, Sir George Yeardley, Richard Berkeley, and George Thorpe had formed a partnership and plans for a private colony to be settled in Virginia. Woodlief was serving the partnership as Captain as well as manager for colony known as Berkeley Hundred. When the ship Margaret arrived on 4 December 1619, Capt. John Woodlief, as instructed by the proprietors, proclaimed the "first" Thankgiving observance in the New World. The Virginia Thanksgiving was essentially a prayer service and not a feast. Woodlief’s instructions stated: “"Wee ordaine that the day of our ships arrivall at the place assigned for the plantacon in the land of Viginia shall be yearly and perpetualy keept holy as a day of thanksgiving to Almighty God."  These words can be found today inscribed in a brick gazebo on the site where Woodlief and the settlers knelt in prayer so many years ago. Two US Presidents have recognized the claim of Berkeley Plantation in Virginia as the site of the first Thanksgiving in America. President Abraham Lincoln visited Berkeley twice in the summer of 1862. Being aware of its claim may have resulted in his setting the precedent for America's national day of Thanksgiving by his Presidential Thanksgiving Proclamation of 1863.  Then President John F. Kennedy in his Thanksgiving Proclamation for 1963 also mentioned Virginia as a site of the first Thanksgiving. 
As for John Woodlief, he was fired as plantation manager for Berkeley in 1620. On December 10, 1620 Capt. John Woodlief acquired from Sir George Yeardley, governor of the Jamestown colony, 550 acres on the south bank of the James river almost directly across from the Berkeley plantation in the Territory of Great Weyanoke, Charles City County. (date of grant from Boddie, p194) He settled down to live the life of a Virginia planter and we do not know what happened to him after 1620.
The date 1637 Virginia has been given for John Woodlief’s death although there is no apparent documentation. John Bennett Boddie in his Virginia Historical Genealogies noted on p 193 that Woodlief was not listed in the muster roll of settlers of 24 February 1624/1625. Boddie states that Woodlief must have been in England at the time although he later acknowledges that he might have been killed in the Indian massacre 26 February 1622. 
On 16 Nov 2017 at 15:36 GMT SP Estes wrote:
this looks to be a duplicate. let's merge and see where the connections take us.
On 2 Dec 2016 at 21:05 GMT Connie (Daniels) Graves wrote:
Just wanted to let you know I have added a bio, some sources and dates to this profile. It will be used for the Biography Builders Nov/Dec. on Wikitree.  Thanks, Connie