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A HISTORY OF GWYNN'S ISLAND

Gwynn’s Island is situated in Mathews County, Virginia, at the mouth of the Piankatank River on the western shore of the Chesapeake Bay approximately 80 miles east of Richmond and the same distance north of Norfolk by road. About 4 miles long and 3/4 miles wide, the year round population is close to 800. The formation of Mathews County originated from the establishment of a very large York County in 1634. In 1651, Gloucester County broke off from York County to the south. For nearly 140 years, current Mathews County was a part of Gloucester County until 1790.

Prior to the arrival of the colonists from Jamestown and Captain John Smith, little is known of its previous history. Indians inhabited the Island around 10,000 BC and left evidence behind with numerous artifacts including arrowheads, tools, pottery, beads, and many other items. Many of these items are on display in our Indian Artifact Exhibit here at the Museum. 

Around 1610(ca) Hugh Gwynn (often referred as Sir Hugh Gwynn, Colonel Hugh Gwynn) arrived in Jamestown possibly with members of his family. The name Gwynn has various spelling configurations, seen as Gwin, Gwinn, Guinn, Wynn, Wynne or Winn. Of Welsh origin, the name Gwynn means “white” and can be traced back as direct descendants of Caractacus, son of King Cymbeline, one of the early kings in Wales. According to history, in 47 AD, Caractacus refused to submit to Claudius the Roman Emperor who conquered Britain. After inciting tribe after tribe to revolt, he finally surrendered to the Romans. Because of his nobility and the renown of his heroism, he gained the admiration and respect of Claudius and was allowed to remain in practical freedom in Rome. 
When visiting the Museum, see the Gwynn's Island & the Roman Connection display.

Around 1611(ca), Hugh Gwynn was exploring the Chesapeake Bay and stopped at a small island at the mouth of the Piankatank River. Legend has it that he heard cries for help from an Indian girl who had fallen from her canoe. Seeing her in the water, he dived in and pulled her to safety. When asked her name she replied “Pocahontas, daughter of Chief Powhatan." In gratitude for saving her life, she gave the island to Hugh Gwynn - Gwynn's Island was born. We believe that Hugh Gwynn, like so many of his compatriots, claimed the Island in the name of King James VI. (known James Charles Stuart and later James I as King of Scotland & England)

In 1635, Hugh Gwynn made a claim to King Charles I of England for property on Gwynn’s Island. About 5 years later in 1640, Hugh Gwynn's request was granted by patent 1000 acres, nearly a quarter of the Island. It is uncertain the gap in time from discovery of the Island in 1611 and 1640 but we do know that Hugh represented Charles River County in the House of Burgesses in 1639. He served as a Justice in York County in 1641 and subsequently represented York County as Burgess in 1646. Hugh finally served as a Burgess for Gloucester County in 1652, indicating that he was either an Island resident or lived nearby until his believed death around 1654.


The name “Gwynn” is now extinct on the Island after much of the originating family moved to North Carolina in the 19th century. The Welsh influence on the Island is indicated not only by Gwynn, but also the surname Edwards. Referencing the bird's eye view of the Island above, Edwards Creek is named after the Edwards Family who has resided on the island since the 17th century. Milford Haven, a body of water between the Island and the mainland, was named after an old fishing town on the southwest coast of Wales. 


Early settlers did a little farming on the Island. Instead, they owned cattle, sheep, hogs and took advantage of the bounteous harvest from the surrounding waters.

Gwynn’s Island played a small yet significant part in the American Revolutionary War.  On January 1, 1776, civil unrest & rebellion began in Norfolk, Virginia about 70 miles to the south of Gwynn's Island, infamously known as the Burning of Norfolk. Lord John Murray, 4th Earl of Dunmore, the last Colonial Governor of Virginia, was forced to leave Norfolk because of civil unrest & rebellion by American Whig (Patriot) forces. Defeated by the Patriots, Lord Dunmore sailed up the Chesapeake Bay to Gwynn’s Island in 1776 with 82 ships in his command. He entrenched himself with 100 soldiers of the 14th Regiment, 100 marines, 150 volunteers from Norfolk, 50 seamen, and about 300 African-Americans for many months on Gwynn's Island. General Andrew Lewis was sent to dislodge him and set up fortifications on the mainland at what is now known as Cricket Hill with mounted cannons.  On July 9, 1776, General Lewis opened fire on Dunmore’s ship, causing considerable damage, initiating the Battle of Cricket Hill. The Dunmore was hit over a dozen times with one casualty and sailors wounded, including Lord Dunmore himself. One of the canon balls breached his cabin, smashed the governor's china sending debris into his leg. The one-sided fight was soon over and Dunmore fled to New York with his remaining forces on July 13. They were rebuffed there and soon left the Colonies for a return to England. Lord Dunmore was the last Royal Governor of Virginia and America would soon no longer be under British rule. 

Life continued on the Island with very few changes for the next 150 years. Sail changed to steam-powered and in the early 1900's the first automobiles appeared on the Island. However, the main method of transportation for many more years was by horse & buggy or boat. Access to the Island was dependent on the ferry until 1939 when the Gwynn's Island Bridge was built. There would never be the sense of isolation from the mainland thereafter.

In August of 1933, a 12-foot storm surge from the catastrophic 1933 Chesapeake-Potomac Hurricane rolled up the Chesapeake Bay, causing major damage to the Island & surrounding areas. The center of the devastating storm passed 15 miles west of the Island and fortunately no lives were lost. However, livestock, boats and buildings were swept away; it took residents several years to recover. 

**Please note the apostrophe "S" in Gwynn's Island.  For many years, State and Federal documentation incorrectly referred to the Island as "Gwynn Island." The late Mrs. Eleanor Respess, a native Islander, prevailed at great length for the change to "Gwynn's Island." Eleanor eloquently said, "You don't call it Martha Vineyard, so you don't call it Gwynn Island!"