An aerial view of Gwynn's Island in Mathews County. Photo courtesy of Gwynn's Island Museum.
At the southern end of the Piankatank River, deep in northeast Mathews County, lies a tiny island accessible only by a swing-bridge. Travelers who choose to go off the beaten path will discover a true gem of Virginia’s heritage upon arriving on the remote, 3.5-square mile body of land known as Gwynn’s Island.
After a visitor crosses the Milford Landing waterway, Gwynn’s Island slowly unfolds. A public pier with a restaurant being built, residents taking in the views, and boats with merry passengers being loaded and offloaded, are warm and welcoming sights to visitors. Traveling deeper into town, the well-paved roads are dotted with bungalow-style homes, proudly adorned with flags and Chesapeake Bay-style décor. Closer to the beaches, large capes and chalets are nestled between smaller cottages. The entire island evokes the feeling of a seashore vacation getaway, with sandy beaches and impressive water views. It is only upon a closer look that visitors realize that the depth of history the small island has to offer is not only impressive, but also includes some of the most impactful records of our national history.
Gwynn’s Island Museum, dedicated to preserving its local culture, is packed with amazing historical relics, pictures and documents. Photo by Dianne Saison.
Originally part of Powhatan lands, Gwynn’s Island got its current name after an unlikely interaction between Colonel Hugh Gwynn, a Jamestown colonist from England, and one of the most beloved figures of Native American history. Legend tells that in 1611, Gwynn was exploring the Chesapeake Bay when he heard cries for help from an Indian girl who had fallen from her canoe into the deep, cold waters. Not about to let the child drown, Gwynn rushed to her aid, diving into the Piankatank River and pulling her up from the waters. Once safely ashore, the young girl introduced herself. Her name was Pocahontas, daughter of Chief Powhatan.
In gratitude for saving her life, Gwynn was gifted the island by Pocahontas. In 1635, Gwynn then claimed the island in the name of the King through the process of headrights. In that time, it was common in Virginia to be awarded lands, instead of money, according to the number of people that an individual financed and/or brought over from England to colonize the Americas. Gwynn’s Island, therefore, was actually a part of the original Jamestown Settlement, as Gwynn himself had arrived and claimed the land under those auspices. According to the patent, Gwynn received 1,000 acres of land at the mouth of the Piankatank River, including much of Gwynn’s Island and land on the south side of Milford Haven.
Whether Gwynn lived on the island, or merely settled his servants and colonists there, remains uncertain. However, he continued to expand his holdings throughout the remainder of his life while also serving in public office. Gwynn represented Charles River County in the House of Burgesses in 1639, served as a justice in York County in 1641, represented York County as a burgess in 1646, and served as a burgess for Gloucester County in 1652, the latter of which indicates he was resident on or near his island by 1652.
The original Gwynn’s Island Ferry, pictured here circa 1912, was hand-pulled and carried goods, visitors and residents across the waters. Photos courtesy of The Gwynn’s Island Museum.
For the next century, Gwynn’s Island residents mainly tended to farming, herding and fishing. The Keeble family, along with the Grymes family, bought land from Gwynn’s descendants and expanded their families on the island. It was a quiet existence, but with the advent of the Revolutionary War came a small skirmish that became a far-reaching, pivotal point in Gwynn’s Island and national history.
In late spring of 1776, John Murray, known as Lord Dunmore and the last Royal Governor of Virginia, encamped his forces on the island. Earlier that month, Dunmore had been anchored near Norfolk. An unpopular man, Dunmore was known for creating and meting out his own brand of law against colonists. Calling his rules “the King’s Justice,” Dunmore alienated Virginians by disbanding their legislative group, denying colonists any representation and creating his own dictatorship in the name of the monarchy.
Learning that American forces were preparing to attack his smallpox-weakened troops, Dunmore raided a colonial armory in Williamsburg, gathered up his Tory sympathizers and led them to the safety of a 90-ship fleet harbored near Norfolk. He then armed his private militia of approximately 600 freed slaves, which he named his “Ethiopian Brigade.” Dunmore led the fleet, packed with as many militants and sympathizers as he could rally, and sailed to Gwynn’s Island, the home of acquaintance and loyalist John Randolph Grymes. At that time, Dunmore had been assured by Captain Andrew Snape Hamond, the senior British naval officer in the Chesapeake, that Gwynn’s Island was an easily defendable refuge with an excellent harbor.
Beautiful inlets provide easy water access to year-round and summer residents of Gwynn’s Island. Photo by Dianne Saison.
On May 26, 1776, Dunmore landed a combined force of about 800 men, including his own 14th Regiment, the Royal Marines, loyalists from Norfolk, sailors, and the Ethiopian Regiment. Once there, Dunmore’s forces built two batteries and a stockade fort on the southeastern tip of the island, while British ships secured the water approach. Dunmore hoped also to set up a safe camp where his sick and dying troops, who were suffering from smallpox and the plague, could rehabilitate while he re-established his royal governorship of Virginia.
American General Andrew Lewis answered Dunmore’s threat. He and four companies of men from the Gloucester County battalion erected the earthworks known as Fort Cricket Hill, the remnants of which survive archaeologically to the present day. By early July, Lewis acquired canons, and on July 9, 1776, American forces opened fire on the British ships. The Otter and the Dunmore both sustained serious damage, with reports that Dunmore himself was injured after a canon came through his stateroom, shattering his fine china and raining debris on him while another shot killed his boson. In addition, four tenders ran aground, one was captured, and five burned. The Virginia regiment then turned its canons on Gwynn’s Island and the embankment on its southern edge. The battle’s finale became the bloodiest day in local history. Dunmore’s men were decimated, with the cannons wreaking havoc. Once Lewis crossed the waters onto the island, none of the royal supporters were left alive. The island belonged to the dead and wounded, many left where they lay. Dunmore, realizing he would receive no aid from the British forces, fled, never to be heard from again. Gwynn’s Island was therefore the last home to Virginia’s final Royal Governor.
Fishermen bring in their shad to Callis Wharf after a hard day of fishing. Photo courtesy of Gwynn's Island Museum.
Gwynn’s Island transitioned peacefully into independence. Residents moved back to the island, resuming their quiet farming and watermen life. The Gwynns and Keebles continued to be the predominate names associated with the island. From 1798 to the 1830s, James Gwynn and his family operated a store on the island, and Humphrey Keeble operated as a licensed merchant and shipbuilder. Gwynn’s Island slowly began to move away from a heavy reliance on agriculture, and more towards a diversified economy that drew merchants, fishermen, and men in the shipbuilding trades to the island. One of the notable new businesses was Mathews Built Schooners, a major sail-powered, ship-building company. The money crop, however, soon proved to be oysters.
According to local watermen, in the bygone days, Gwynn’s Island’s waters were so inundated with oysters it became hard to come ashore in some areas, as the oysters were so abundant and deadly sharp they would tear up and peel away entire hulls. Although the island saw little action during The Civil War, it benefited greatly from Reconstruction, as steamships from Baltimore brought travelers and the water trade flourished. Goods from Baltimore were brought in to the island for sale to the surrounding region while oysters and harvested fish were exported by the ton.
The travel and the commercial seafood industry shaped the daily life of Gwynn’s Island’s community well into the twentieth century. The best surviving example of this on the island is Callis Wharf, which today operates as Oyster Seed Holdings. Captain William James Callis built the wharf in the late nineteenth century, and his son, W. Eugene Callis, improved it in the early twentieth century. Soon after, the Maryland Steamboat Company and the Chesapeake and Atlantic Steamboat Company, began using it for passenger travel. By 1912, the wharf also supported a seafood packing house, commercial traffic, passenger traffic, and live entertainment, including the James-Adams Floating Theater, which inspired the Edna Ferber classic, Showboat.
Callis Wharf, circa 1960, was the hub of Gwynn’s Island and even featured a grocery store. Photo courtesy Gwynn’s Island Museum.
During the decades between the Civil War and World War I, the growing community on Gwynn’s Island used resources from fishing and farming to seat itself firmly in the modern era. In 1883, the people of Gwynn’s Island built their first post office, and during the summer of 1883 the community, spearheaded by the women of the island, who were tired of not being able to travel across the waters without getting wet, raised funds to launch a ferry service between the island and the mainland.
In 1924, The Mathews Journal reported that the Gwynn’s Island Fish and Oyster Company produced 108,000 cans of herring and 2,000 barrels of “rightly packed herring.” Gwynn’s Island had become the center of heavy investment in seafood processing. In addition to the Gwynn’s Island Fish and Oyster Company, it was also home to the Mathews Seafood Products Company, J. Newton Foster & Son, the Gwynn’s Island Operating Company, and the Great Atlantic and Pacific (A&P) Tea Company.
Although tough times hit Gwynn’s Island, along with the rest of the country, during The Great Depression — which caused A&P to shutter its island operations — the fishing industry remained strong, and the demand for seafood during World War II brought another wave of prosperity. The construction of W. D. Jenkins’s marina complex, beginning in 1964, helped reinforce the increasingly recreational nature of Gwynn’s Island’s economy.
The molar of a mastodon, discovered alongside a cast of the Cinmar Knife and a portion of mastodon tusk, are all on display at the Gwynn’s Island Museum. Photo by Dianne Saison.
Arguably the most exciting and impactful event in Gwynn’s Island’s recent history involved the discovery of ancient bones and tools, the likes of which have rewritten history books concerning early man. In 1970, Captain Thurston Shawn of Mathews was dredging for scallops on his boat the Cinmar, 40 miles off of the Virginia Capes, when he pulled up an ivory mammoth tusk, a large molar and a stone knife.
Shawn later donated those items to the Gwynn’s Island Museum. Just over a decade ago, an archaeologist from the Smithsonian Institution in Washington, D.C., went into the local museum seeking shelter from a rain storm and happened upon the displayed items. His reaction was immediate, calling his boss and directing a team of scientists to investigate what he felt to be a hugely significant discovery. After two years of testing, including carbon dating and DNA tests, it was concluded that the molar was from a 30-year-old female mammoth who died 20,000 years ago. The knife, now named The Cinmar Knife, after Shawn’s vessel, became the oldest paleo-human artifact to be discovered in the Americas. Researchers have since been able to determine that the knife had European origins, and that hunters and gatherers once crossed the North Atlantic in ice boats, coming to the region to hunt large game. The original knife, which will be displayed at The Smithsonian, was replicated and is on display at the Gwynn’s Island Museum along with the original tusk and molar Shawn discovered.
The Cinmar Bi-Faced knife, dredged up by a Mathews waterman, is the oldest known artifact of Paleo-humans ever found in the Americas. Photo courtesy The Gwynn’s Island Museum.
Today, the community on Gwynn’s Island seamlessly reflects its colorful history while embracing modern values and comforts. Perhaps the most important place that is reflected is at the Gwynn’s Island Museum. From its creative display of Gwynn saving Pocahontas, to the Cinmar exhibit, to the Merchant Marine and Military room of honor, to the hundreds of pictures depicting daily life though the island’s history, the museum has created a bastion of both preservation and learning for visitors and residents alike.
Between the beautiful beaches, friendly island folk, up-and-coming restaurants, and the rich historical tapestry, Gwynn’s Island stands unique in both its beauty and breadth of history readily accessible and just waiting to be discovered by the intrepid traveler.
The House and Home Magazine would like to extend warm thanks and appreciation to The Gwynn’s Island Museum, its director Tom Edwards, and all of the residents who helped compile their island’s history. For more information on Gwynn’s Island, visit www.gwynnsislandmuseum.org.