Capt. John Littlefield Sr. was born about 1624 in Titchfield, Hampshire, England, baptized there on 1 Nov 1624. Or, he was born between 1625 and 1630. He was a constable in 1661. He died on 9 Feb 1696/97 in Wells, York Co., Province of Maine, Massachusetts.

John Eldridge Frost, MAINE PROBATE ABSTRACTS, Vol. 1, 1637 - 1775; Picton Press, Camden, ME 1991: P. 64 - 

"CAPT. JOHN LITTLEFIELD, of Wells. Est div (2.2/73). F11828. Agreement of & Oct 1701 bet Patience Littlefield, wid, of Capt. John Littlefield of Wells, decd int, Josiah Littlefield, Eliab Littlefield, for himself & as atty for Liddin [Lydia] Storer, d of Capt. John Littlefield, Samuel Webber, for Himself & his w Deborah, another d, Matthew Austin, for himself & his w Mary, another d. William Webb, for himself & his w Charity, another d, Josiah winn, for himself & his w Liddia [sic], a g d & only c of John Littlefield, decd, eld s of Capt. John Littlefield, edward Beale, for himself & his w Elizabeth, another d of Capt. John Littlefield, Joanna Littlefield, wid, & d-in-l of Capt. John Littlefield, Mercy Lufkin, wid, another d, & James Webber, for himself & his w Patience, another d, dividing the est of Capt. John Littlefield [a detailed div embracing both real est & pers, too extensive for incl of details]; allowed, 7 Oct 1701. Est div incl land & marsh on the house side of the river, dwelling house, saw mill & our houses divided; 1/2 to wid ["our mother"], for life, plus use of W end of dwelling with milk house & garden; other 2/3 equally divided among chn, with exceptions. Mentions also marsh & thatch on beach side of river, & misc lots of marsh & land."

William M. Sargent, A.M., MAINE WILLS 1640-1760, 1972, p 4. Mentioned in father's will.

He was married to Patience Wakefield in 1645 in Gloucester, Essex Co., Massachusetts.

Patience Wakefield was born about 1624. She died after 7 Oct 1701 in Wells, York Co., Province of Maine, Massachusetts. Children were:

i. Charity Littlefield was born about 1650 in Wells, York Co., Province of Maine, Massachusetts.
ii. John Littlefield Jr. was born about 1651 in Wells, York Co., Province of Maine, Massachusetts.
iii. Lt. Josiah Littlefield.
iv. Eliab Littlefield was born about 1654 in Wells, York Co., Province of Maine, Massachusetts. He died about 1713/14. He was a miller.
v. Samuel Littlefield was born about 1656 in Wells, York Co., Province of Maine, Massachusetts. He died before 1701.
vi. Lydia Littlefield was born about 1658 in Wells, York Co., Province of Maine, Massachusetts. She died after 1701.
vii. Mary Littlefield was born about 1662 in Wells, York Co., Province of Maine, Massachusetts.
viii. Deborah Littlefield.
ix. Patience Littlefield was born about 1665 in Charlestown, Suffolk Co., Massachusetts where she was baptized on 23 Apr 1699. She died after 1748 in Medford, Middlesex Co., Massachusetts.
x. Elizabeth Littlefield was born about 1666 in Wells, York Co., Province of Maine, Massachusetts. She died after 1747.
xi. Mercy Littlefield was born about 1668 in Wells, York Co., Province of Maine, Massachusetts.