A Brief 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, although it seems more like 8000 in the summertime. 

Prior to the arrival of the colonists from Jamestown and Captain John Smith, little is known of its previous history. We do know that Indians inhabited the Island s inhabited the Island ast 10,000 BC as evidenced by the numerous artifacts...arrowheads, tools, pottery, beads etc...and many of these items are now in the Gwynn’s Island Museum

In 1610(?) Hugh Gwynn, often referred to by some as Sir Hugh Gwynn, and by others as Colonel Hugh Gwynn (probably the latter) arrived in Jamestown possibly with members of his family. The name Gwynn is variously spelled 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. 

(See Gwynn’s Island & the Roman Connection at the Museum) 

In 1611(?), 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 about to sink, he dived in and pulled her to safety. When asked her name she replied “Pocahontas, daughter of Chief Powhatan", and in gratitude for saving her life she gave the island to Hugh Gwynn, hence the name Gwynn’s Island. besides, Hugh figured it was easier to spell Gwynn than Pocahontas. Chances are that Hugh Gwynn, like so many of his compatriots, claimed the Island in the name of the King, and settled in for the duration. 

What is now Mathews County was formed from Gloucester County in 1790, and Gloucester County was formed from York County in 1651 which itself was formed in 1634. In 1635, Colonel Hugh Gwynn made a claim to King Charles 1 of England for property on Gwynn’s Island, and was granted by patent 1700 acres, almost a quarter of the Island, in 1640. Why the time lag between his discovery of the Island in 1611 and 1640 we don’t know. He became a member of the House of Burgesses in 1652 from Gloucester and a leading vestryman in the church and died about 1654. He had also been a member from York County in 1639 and 1646, and a Justice in 1641. The name “Gwynn” is now extinct on Gwynn’s Island, much of the family having moved to North Carolina in the 19th century, but there are lineal descendants still living there. Gwynn is a fairly common name in the general area among both black slave descendants and whites. The Welsh influence on the Island is indicated not only by Gwynn, but also the name Edwards, and the fact that the body of water between the Island and the mainland coming in from the Bay is called Milford Haven, named after an old fishing town on the southwest coast of Wales.  The Gwynns and the early settlers did a little farming, owned cattle, sheep and hogs and took advantage of the bounteous harvest from the surrounding waters. Slaves were brought to the island by the Gwynn's, the Keebles, the Readesand the Hudgins who also owned fairly large properties at that time.  

Gwynn’s Island played a small but significant part in the Revolutionary War.  After Lord Dunmore, the last Colonial Governor of Virginia, was forced to leave Norfolk because of unrest and rebellion by the local population, he sailed up the Bay to Gwynn’s Island in 1776. He entrenched himself with 500 men, many runaway slaves, and several ships for many months. General Andrew Lewis was sent to dislodge him and set up fortifications on the mainland at what is now known as Cricket Hill and mounted his guns.  Opening fire on Dunmore’s ship, he caused considerable damage. The fight was soon over and Dunmore and the remnants of his flotilla fled up the Bay to Maryland. They were rebuffed there and eventually left the Colonies and returned to England. The Revolutionary War was under way, and America would no longer be under British rule. 

Life continued on the Island with very few changes for the next 150 years. Sail changed to steam and in the early 1900's the first automobiles appeared, but transportation for many more years was by horse and buggy or boat.  

In August of 1933 a twelve foot wave rolled up the Chesapeake Bay from a terrible hurricane and caused major damage to the Island as well as to other areas. Fortunately no lives were lost but livestock, boats and buildings were swept away. It was a major disaster for the Islanders and it took several years to get back to normal. 

For many years during the late 1800s, early 1900's, access to the Island was by ferry, but in 1939 the Bridge was built and there would never be the sense of isolation from the mainland thereafter.

If you would like to learn more about the Gwynn family, we recommend Happy Valley by Thomas Felix Hickerson.  Out of print and hard to find, this is an authoritative reference.  Can occasionally be found on the Web at 
www.abebooks.com or other good used book stores and will probably be expensive.

** Please note the apostophe 'S in Gwynn's Island.  For many years State and Federal maps and charts referred to it as Gwynn Island.  Unfortunately some current publications still do.  The late Mrs. Eleanor Respess, a native Islander, prevailed at great length to get it changed to Gwynn's Island, saying "You don't call it Martha Vineyard, so you don't call it Gwynn Island!"