Andrew Lester, born c1615, and his family are somewhat of a mystery, as he left relatively few records in the colonies in his lifetime.

Andrew Lester’s name doesn’t appear in Gloucester, Essex, Massachusetts records until the birth of his son, Daniel, in 1642.

Whether he married wife Barbara (MNU) in England or Massachusetts is not known. However, he was admitted a freeman of the colony on 10 May 1643, after having been appointed Gloucester constable a few months earlier.

The status of freeman was generally given after a 1-2 year probationary period of residence in the colony, so he likely arrived from England in 1641 or 1642.

In 1648, Andrew was licensed by Essex County Court to keep a house of entertainment.

However, on 19 October 1650, Andrew Lester and several other Gloucester men (the Cape Ann Company) were granted land at Pequot, later to become New London, Connecticut. Rev. Richard Blinman, originally from Wales, then Plymouth and Gloucester, Massachusetts, was to be their minister.

Andrew Lester sold his property in Gloucester in 1651 and left for the Pequot Plantation.

The births of four children were recorded in Gloucester:

1. Daniel, born 16 April 1642
2. Andrew, born 26 December 1644
3. Mary, born 26 December 1647
4. Ann, born 21 March 1650

Barbara died in New London, Connecticut on 2 February 1653/54, being the first death of a woman in Pequot.

Andrew married (2) Joanna Hempstead, widow of Robert Hempstead. Joanna died and the couple apparently had no surviving children. He married (3) Anna/Hannah (Brooks) Fox, widow of Thomas Fox. They had three children together:

5. Timothy, born 4 July 1662
6. Joseph, born 15 June 1664
7. Benjamin, born c1666

Andrew reportedly left a will dated 7 January 1667, recorded in the New London, Connecticut probate records, Volume 2:4. However, I have not been able to find even a transcription of that will.

What is interesting about this family is that Andrew’s entire family remained in Connecticut after they moved in 1651 – EXCEPT for my ancestress, Ann.

It has been suggested that Ann was taken in perhaps by her mother’s family back in Gloucester after Barbara died. Ann married Nathaniel Millet in Gloucester on 3 March 1670, when Ann wasn’t quite 20 years old. How I wish someone had recorded the guardian who gave permission for her to marry under the age of 21!

What is uncertain, though, is whether her guardian’s family ever lived in Gloucester when the Lesters did or if they arrived later.

Unfortunately, it seems that no one has uncovered any possible clues as to Ann Lester’s guardian, nor has it been proven exactly when she returned to Massachusetts. Being the youngest child, she may have left Connecticut about 1667 after the death of her father.

Babson’s History of Gloucester, Massachusetts includes a handy list of settlers in town by 1650.

I’ve crossed out the men who removed to New London, Connecticut and I’ve also eliminated several ancestral lines of my own, as no ties have been discovered to the Lester family through them.

Immediately after this list in Babson’s book, he wrote short sketches for many of the early families who lived in Gloucester before 1700.

I then eliminated more names of men who disappeared early with nothing more known about them or who removed to Falmouth, Maine or elsewhere.

That left only a few early families:

Babson, Isabel
Babson, James
Bray, Thomas
Evans, William
Elwell, Robert
Glover, Stephen
Hill, Zebulon
Jones, Thomas
Kettle, John
Martin, Solomon
Pearse, John
Prince, Thomas
Somes, Morris
Very, Thomas

Of these names, several have close ties to the Millett and Witham families – Babson, Hill, Elwell, Prince and Somes.

Could the Lester connection be hidden in one of these families? I don’t have the answer, just a maybe.