General Joseph Martin Chapter

Cumberland Gap, TN


Cumberland Gap Patriot

Richard Winchester


Richard Winchester was born February 15, 1755 in Hartford Connecticut.
In February 1777, Winchester joined the CT Militia under Captain McPherson.
His first battle would be the battle of Ridgefield CT fought on April 27,
On April 27, 1777, the British landed in Connecticut and marched to
Danbury Ct and burned it to the ground. Danbury was a supply depot used by
the Continental army. During the war Connecticut would send more food and
ammunition to the Continental army than another colony in New England. At
Danbury, the British destroyed 5000 barrels of pork, beef, flour and 2000
bushels of grain. On Clothing, 5000 shoes and 1600 uniforms, 1600 tents and
winter blankets were also destroyed. In the town 19 houses were burned to
the ground.
After the British burned Danbury they marched to Ridgefield CT. There
Winchester and 600 other militia members under the command of Benedict
Arnold and General Wooster fought the British.  Out numbered 3 to 1, the
Americans soon had to retreat. Even though they lost the battle they were
able to stop the British and force them to return to New York. The British
had 140 killed and 20 taken prisoner. The Americans had 20 killed and 80
wounded. General Wooster was killed making him the first Connecticut general
to die in the war.
On August 27, 1778, Winchester participated in the battle of Rhode
Island. The Battle of Rhode Island was an attempt to secure a base in Rhode
Island for French ships to leave supplies. The battle was at best a draw
leaving the Continentals unable to secure a base of operations in Rhode
Island. Also in 1778, Winchester met Lydia Dodge and soon married her. From
this union they had 1 child.
On September 6, 1781, Winchester fought in the battle of Groton
Heights. This battle is also referred to as the Fort Griswold Massacre.
Winchester and over 150 CT militia under the command of Col. Ledyard fought
bravely against the 800 man British army under the command of then traitor
Benedict Arnold and Col. Eyre,  but was soon overwhelmed and forced to
surrender.  At the surrender, Col Eyre struck a blow with his sword
decapitating Ledyard. This started a wholesale massacre of the Ct militia
inside the fort. Benedict Arnold just watched doing nothing to stop the
massacre. Over 80 Ct militia men would die during this massacre. The
massacre at Fort Griswold would have the same effect among the people of
Connecticut that the battle of the Waxhaw had in South Carolina in May 1780.
Winchester barely escaped the massacre with his life running into the hills
around New London CT.
After the battle of Groton Heights, Arnold ordered the town of New
London burned to the ground. Over 143 buildings were burned to the ground.
Winchester could do nothing but watch in anguish of the devastation caused
by Arnold and the British Army. During the Revolutionary war 4 Connecticut
towns were burned to the ground. After the war any family in Connecticut
that lost a house or any business property to the British were given free
land grants in the state of Ohio.
In 1783, Winchester brought his family through Cumberland Gap to
Boonesborough KY. In 1810 Winchester moved to Hardin County KY. On October
14, 1859 at the age of 104, Winchester died and was buried on his farm.  In
1859, Winchester was one of the oldest and last remaining patriots in the
State of Kentucky and the United states.
During the Civil war descendents of Winchester fought in both Union and
Confederate armies. Hardin County KY was a Union stronghold. It contained a
garrison and a supply depot that supplied the Union army in Southern KY. On
December 25 1862, General John Hunt Morgan leader of the Confederate
Cavalry, in his famous Christmas raid destroyed the Union garrison in Hardin
County and destroyed the train trestle at Muldraugh Hill. Destroying this
train trestle disrupted supplies to Union troops in Southern KY for 3 months
forcing many Union troops to retreat from the region.
Today most of Winchester's descendents live in western KY.


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