M. about 1631 in England
Wife: Mary (probably) Wade
D. 11 Dec 1648 in Wethersfield, Connecticut
As the original Puritan settlers of New England pushed inland, they often needed to carve communities out of raw wilderness. Leonard Chester was such a settler, and one trek into the woods made him a local legend. He was born in Blaby, England, a village in Leicestershire, on July 15, 1610. His parents were John Chester and Dorothy Hooker, and he was their only surviving child. Leonard’s father died in 1628.
In about 1631, Leonard married a woman named Mary. Her maiden name is uncertain; it’s given as Wade, Sharpe and Neville in different sources. Leonard and Mary sailed for America two or three years later. The next two years, they lived in Watertown, Massachusetts, where Mary gave birth to their oldest child, John. Leonard’s mother was the sister of Reverend Thomas Hooker, who in 1635 helped lead a migration of people that founded Hartford, Connecticut. Leonard wasn’t part of that group, but his mother was, and within a year, Leonard and his family moved to another new settlement nearby called Wethersfield.
One day in September 1636, Leonard was seeking a location to build a grist mill, and he followed a stream hoping to find an appropriate spot. He went too far and couldn’t find his way back before it got dark, so he was forced to spend the night alone in the woods. Instead of camping out, he continued to wander in the dark, straying completely off track. He was said to have become afraid, hearing wolves and other strange sounds that made him imagine he was in great danger. His adventure went on a second day and night, and at dawn of the third day, he found himself at the foot of a mountain. Climbing to the top, he could hear sounds that traveled several miles — the people in his town were beating kettles and shooting off muskets to get his attention. He descended again and was able to follow the sounds back to civilization. The people in town had “lamented” that he was lost, and when he returned, he told the story of the mountain that saved him, which is known to this day as Lamentation Mountain.
Lamentation Mountain is now a state park in Connecticut.
Besides the story of getting lost in the wilderness, Leonard was known as one of the early leaders of Wethersfield and a man of some wealth. He wrote his first will in 1637 while still in his 20s; this was likely because he owned property in England and he wanted to make sure his family would hold title to it in case something happened to him. Also that year, he built the grist mill that had caused him to wander into the woods. It survived for many years.
In addition to their oldest son, Leonard and his wife Mary had six more children, all born in Wethersfield. Unfortunately, Leonard didn’t live to see any of them grow to adulthood — he died on December 11, 1648. His grave is said to be the third oldest tombstone in Connecticut; it’s a large slab of red sandstone with the coat of arms of the Chester Family carved into it. His wife Mary remarried and lived until about 1689.
Leonard’s descendants include Calvin Coolidge and Bette Davis.
Children:
1. John Chester — B. 3 Aug 1635, Watertown, Massachusetts; D. 23 Feb 1698, Wethersfield, Connecticut; M. Sarah Welles, 2 Feb 1654, Wethersfield, Connecticut
2. Dorcas Chester — B. 1 Nov 1637, Wethersfield, Connecticut; D. 15 Feb 1712, Billerica, Massachusetts; M. Samuel Whiting (1633-1713), 12 Nov 1656, Wethersfield, Connecticut
3. Stephen Chester — B. 3 Mar 1640; D. 23 Apr 1705, Wethersfield, Connecticut
4. Mary Chester — B. 15 Jan 1641; D. 15 Sep 1669, Wethersfield, Connecticut
5. Prudence Chester — B. 16 Feb 1643; D. 21 Oct 1678, Charlestown, Massachusetts; M. Thomas Russell (1641-1676), 30 Dec 1669
6. Eunice Chester — B. 15 Jan 1645; D. 27 May 1676, Charlestown, Massachusetts; M. Richard Sprague, 25 Feb 1673, Charlestown, Massachusetts
7. Mercy Chester — B. 14 Feb 1647; D. 15 Dec 1669, Charlestown, Massachusetts
Sources:
Families of Ancient Wethersfield Connecticut, Henry R. Stiles, 1859
Leonard Chester’s search for a Mill Site – 1636, Wethersfield Historical Society
Transactions of the Leicestershire Architectural and Archaeological Society, Volume 6, 1888
Find a Grave
