Samuel Whitehead migrated to New England during the Puritan Great Migration (1620-1640). (See The Great Migration (Series 2), by R. C. Anderson, vol. 7, p. 351) Join: Puritan Great Migration Project Discuss: pgm
He was granted land in 1634/5 so must have been at least 21 by this time.
Stephen Whitehead, was at Cambridge, Massachusetts, as early as 5 Jan 1634/5 when he received a 2 acre grant. A year later 4 Jan 135/6, "Will Towne shall have the two acres there which Samuell Whithead should have had"
Samuel Whitehead's name is on the Hartford Founder's Monument. There is no record in Hartford of him having acquired the land, but later records show that Richard Lord owned a houselot which he bought of Samuel Whitehead and John Skinner had a small parcel that he bought from Whitehead. These were parcels 57 and 59 1/2 on the map, in the middle of town, across from the meeting house.
New Haven Colony
4 June 1639 Samuel Whitehead, and 62 others, signed the New Haven Fundamental Agreementestablishing the government which would stay in effect until the end of 1665. 6 August 1642 "Brother Abbott and brother Whitehead admitted members of the Court and received the charge of freemen." 1 July 1644, Samuel and the other men in town took the Oath of Fidelity to the government of New Haven.
Living in New Haven required responsibilities to the town and colony. All able bodied men served in the trainband, a military unit for the defense against enemies. The men shared the watch in the wee hours of the night and some were assigned each week to attend services with their arms. Many men, during the early years, held positions in town of one kind or another, from fenceviewers to the Governor. Samuel held the following offices.
New Haven selectman many times between 1652 and 1674.
Samuel fought in the Pequot War, 1637, for which he was awarded 50 acres of land by the Connecticut Colony in 1671. The completion of this war cleared the area of the natives allowing settlements like New Haven. Whitehead was chosen a corporal of the New haven trainband 6 Aug 1642, and ten years later 7 June 1652, Corporal Samuel Whitehead was chosen sergeant. The Sergeant was one of the officers from Milford selected to serve in a planned expedition against the Dutch in 1654. The Connecticut General Court confirmed his position as Sergeant of the New Haven Trainband 6 July 1665 New Haven Colony had given up it's autonomy as a government and joined with Connecticut the previous December. Age became an issue and on 16 June 1673, "Sergeant Samll Whitehead upon his desire, being lame, was freed from being sergeant." 
New Haven Colony was run on Christian principles, using the Bible as it's guide. Samuel and his wife had assigned seats in the meeting house
Samuel acquired a good amount of land during his life.
1640 Early list of estates: 2 persons, estate valued at £60, and approximately 30 acres of land granted by the town in the 1st division, neck, meadow, and 2nd division.
1646 New Haven Book of Alienations: 2 persons, estate valued at £60, and about 50 acres some of which he purchased from other planters.
There are several land transactions buying and selling land in the following years.
22 Feb 1670/1 an inventory of New Haven land was taken. Samuel had several parcels amounting to 47 acres, 102 acres of commonage, his homelot and 14 acres that he had from the town.
20 Dec 1680 Third land division Samuel had 3 heads, an estate of £363, and was granted 84 acres. His third division land was not "land fit to be laid out" and he requested that it be changed.
Before 14 Oct 1686. "Sarjt Whithead and Joseph Moss haveing lost their houseing and great part of their substance by fire, this Court remitt their country rates for this yeare."
Samuel's first wife was never named in the records but in the 1646/7, 1655/6, and 1661 meeting house seating, she had assigned seats.
Samuel Whithead and Sarah Guilbert were married 9 may 1676. Sarah brought two young sons into the household and had two more with her new husband. She was the widow of John Gilbert and the daughter of Thomas and Jane Gregson. She died in 1697.
↑ Source: #Anderson p. 355 citing New Haven Probate 2: 1: 61
Donald Lines Jacobus, Families of Ancient New Haven ([CD]Baltimore, Genealogical Publishing Co., Inc., 1981[originally]Rome, N.Y. and New Haven, Conn., 1922-1932), vol 3, p 642,
Donald Lines Jacobus, Families of Ancient New Haven, vol 8, p 1970. "served Pequot War."
Barbour, Lucius Barnes, 1982, Families of Early Hartford, Connecticut, Genealogical Publishing Co. Inc., Baltimore, Maryland and Connecticut Society of Genealogists, Inc., Glastonbury, Connecticut pp. 675