Issue: August 2003
An Island Apart

Just off the Virginia mainland, Gwynn’s Island always has been and perhaps always will be a unique Bay community.


    Not much in life is certain, but when you wake up on Gwynn’s Island in Virginia, some things you can count on. One is the sea breeze humming through the tall pines, and the smack of the Bay clapping against the island’s eastern shore, music that played here long before humans were around to hear it. Another is the limitless horizon, a quivering plaything of light and water. From a distance the sandy islets beside Hole in the Wall seem to float like dumplings in a sun-flecked soup, and a workboat coming up Milford Haven appears first as a mirage, then slowly takes a solid, familiar form, its cheeky bow carving a shimmering silver sea. There is also Buford, a hound of baggy demeanor, whose coppery back faces the road as he sits on the bench outside the Gwynn’s Island Market & Deli, staring longingly at the goodies within.

    And then, there is the locals’ table at the Seabreeze, situated near the restaurant’s front door beside a big window overlooking the parking lot, launch ramp and bridge to the mainland. Strategically, it’s a perfect location - no one can come or go unnoticed, the coffee pot is practically within arm’s reach, and you can lean back a notch and let the girls in the kitchen know that, yes, they most definitely should set aside a helping of bread pudding for you at lunch. This is where, over the course of a day, you will see many of the island’s residents, most of whom will be happy to tell you a story or discuss current events.

    The talk this rainy morning has touched on many subjects, from the merits of Snap-on Tools (excellent tools, everyone pretty much agrees, but expensive, so you don’t want to use them onboard, lest they go swimming or fall into the bilge and rust all summer), to the mosquito outlook (grim), to the northeaster presently blowing (not too bad), which has flooded the ditches and created a respectable reservoir on the lawn over at the Gwynn’s Baptist Church. There’s constant ribbing and repartee such as: “You ever get tired of having yourself around?” followed by, “Well, I sleep most of the time.” Eventually, the talk turns to those who aren’t here. “Used to be a lot more people sitting at this table - watermen,” says Granville Ambrose. “A lot of watermen now are into trucking, long-distance hauling.”

    “Whatever they can find,” agrees Paul Bing.

    “Whatever pays the bills,” says Ambrose.

    “People lookin’ for easier work,” Bing tells me, when I ask why the numbers are dwindling.

    “And the market’s not there for it,” Ambrose adds.

    “Oysterin’s pretty much just gone,” Bing says.

    “Even pound-netters, most of them are doing it on the side as a second job,” says Bing’s son Steve.

    Over the table, a fan stirs the air. My seat was barely warm before I was warned not to believe anything I heard at the “gossip table” - a kind of blanket immunity for those in attendance - but I’ve heard this same talk elsewhere on the island, and the men grow serious as they discuss what has happened to the seafood industry that only a generation ago still thrived here. Behind their heads, photographs and knickknacks tell more of the story. One black-and-white photo shows a cable ferry pulling up to the beach, delivering a horse and buggy. An old iron workboat wheel hangs near the picture, and a little cupboard on the wall behind the head of the table holds all kinds of treasure that the island’s watermen have dredged up over the years - arrowheads, pottery, clay pipe bowls and stems, enormous shark teeth and fossils. On a little shelf by itself sits a coffee mug, over it a photo of a smart white workboat on a bluebird day, the Stars and Stripes snapping in the air over its cabinhouse. The mug and the boat belonged to Bobby Sadler, a local waterman who drowned about 15 years ago. 

    Ask about this mug and you will get the whole story. That’s the kind of place this is. People are not forgotten, and people go on. Separated from the mainland by a thin neck of water but permanently attached by a bridge, Gwynn’s Island retains a certain insulation from bigger, snazzier, more impersonal places. It is by no means a land that time forgot, but it does recall a different era. Most everyone knows everyone else, and life tends to slow down considerably when you cross that bridge. Some “old-heads” (as the elders are fondly called) still remember that cable ferry, and the arrival at Callis Wharf of the steamboat Piankatank, loaded with goods for the island’s general stores, and they remember the boats, lined up by the dozens at the seafood wharves. Many newer residents spent their childhood summers here and now have put down permanent roots.

    Above the pines, the sky is vast and star-pricked at night, and the broad horizon shimmers on the water all around, but on this island at the edge of the Bay, the world is familiar and warm enough to fit into an old friend’s coffee mug.


On the chart, Gwynn’s Island is shaped like a high, curling wave, about to break on the southern shore of the Piankatank River. The crest is at Cherry Point, which curves slightly northwest to face Stove Point Neck, directly across the Piankatank’s mouth. What would be the wave’s face is a long, straight stretch along Hills Bay, while its back faces due east. The base of the wave is the island’s southwestern edge, which borders Milford Haven, and into which a variety of creeks wiggle and wander. Gwynn’s Island’s eastern side, like that of a coastal barrier island, bears the brunt of the Bay’s weather and suffers the inevitable shifting, eroding landscape (Cherry Point is so named because at one time a cherry tree orchard stretched nearly a mile into the river there), while its body protects the placid and beautiful back bay of Milford Haven, as well as the Mathews County mainland to the west.

    It’s just barely an island. Only about 200 yards of water separate it from the mainland at the narrows between Milford Haven and Hills Bay. Heading south in the haven, that distance widens, until by the time you reach the snaky, shifting channel called Hole in the Wall that leads into the Bay, the island shows its true identity as a mere fragment of spongy, pine-studded earth, afloat in bottle-green water. From Cherry Point down to Sandy Point (the last bit of land before Hole in the Wall) the island is about two and a half nautical miles long, and it’s less than two nautical miles across at its widest. Still, thanks perhaps to its proximity to the mainland, it doesn’t seem quite so ephemeral as those islands to the northeast on the Bay’s other side, Smith and Tangier.

    Johnny and I sailed to Gwynn’s Island last fall from Annapolis, blown like a bit of flotsam before the trailing winds and pouring rain of an outbound tropical storm. We didn’t know what to expect as we flew into the Piankatank River, leaving Stingray Point well to starboard. To our left, Cherry Point slowly emerged from the low fog and gave way to a long stretch of trees and beaches. We dropped our sails in the tidy, calm teacup of Hills Bay and motored toward the narrows. Just before the swing bridge on the left was the Narrows Marina, where we tied up at the fuel dock and eventually tracked down owner Preston Jenkins. Two young sons in tow, he invited us to take any slip we liked, pointed out the showers and the way to the Seabreeze Restaurant, and then left us to squeegee ourselves.

    The Narrows and its adjacent hotel complex, the Islander Motel, has the feel of an old Bay trolley park - a place where you can almost hear the echoes of music and laughter. The two-story motel sits on a broad point facing Hills Bay and the river beyond. Behind the motel, a grove of longleaf pines shelters a little playground and some old wooden boats doing what they must - waiting, and slowly fading. A long dock with finger piers borders the western edge and leads to the fuel dock and the marina proper.

    On the way to the showers I wandered into one of the marina’s long sheds of covered boat slips and found a thriving community of Egg Harbors and Chris Crafts, Grand Banks and a variety of big sportfishermen and smaller cuddy-cabin fishing boats. At the head of nearly every slip, boatowners had personalized their boats’ space with all manner of stuff. Grills, refrigerators, lockers, workbenches, lounge chairs and gear. Boat fenders and outriggers, dog food and Clorox, charcoal, bottom paint, crab nets, life jackets and water skis. “Pray to God But Row Toward Shore!” proclaimed one sign. “If God meant us to have fiberglass boats He would have planted fiberglass trees,” read another - that one in the locker space of an immaculate Post sportfisherman. On land, perhaps, this place may feel like it is waiting for something to happen, but it’s pretty obvious where the action is - on the boats and on the water.

    It was only a short walk from our slip to the Seabreeze, where we enjoyed a fine dinner overlooking Milford Haven. Walking back to the boat under a moon sneaking like a thief through the clouds, all we could hear were the shrill cries of an agitated killdeer, the wind shushing through the huge pines, and a flag snapping in the breeze off Hills Bay.


    For such a relatively small place, Gwynn’s Island has a pretty big history. Beads, tools and points (arrowheads) found on the island reveal that Native Americans lived here more than 10,000 years ago. Jean Tanner, director of the Gwynn’s Island Museum, has found some of this evidence herself while progging the ever-changing shoreline on the island’s southeastern end, where she has lived for 23 years. One of the museum’s exhibits is her own collection of points, one of which is nearly 3,000 years old. Another find, verified by the Smithsonian Institution, is a bryozoan fossil approximately 400 million years old, and local waterman Dean Close one day dredged up a perfect mastodon tooth - also verified by scientists and now on display at the museum.

    The new kid on the block, then, was Colonel Hugh Gwynn, who sailed to Jamestown in 1611. There’s a persistent legend that he saved Pocahontas from drowning while exploring off Gwynn’s Island, and she was so grateful she handed the island over to him. Whether passing truth or pure fiction, the recorded facts bear out that Gwynn in 1640 received a patent of 1,700 acres of the island from King Charles I, and so the place bears his name.

    The island’s most illustrious - or perhaps dubious - moment in American history came in the summer of 1776, when the last royal governor of Virginia, Lord Dunmore, thumbed his nose at the leaders of the breakaway republic, assembled a fleet of over 100 vessels under the Royal Navy flag and sailed them from Hampton Roads to Gwynn’s Island, where he established a military base to thwart what he considered a wrongheaded insurrection against the British crown. “For a short time,” writes Peter Jennings Wrike in his book The Governors’ Island (plural because eventually the royal governor of Maryland joined Dunmore), “tiny Gwynn’s Island became the seat of British royal authority for Virginia and Maryland. From Gwynn’s Island, Dunmore attempted to subdue the rebels and lead the campaign to restore royal authority.”

    Wrike’s book provides a detailed and interesting account of early colonial life on the island from the time of Gwynn’s English settlement. The place seemed ideal for the colonists’ purposes; the low land was fertile, longleaf pines and hardwoods meant abundant lumber, wells supplied sweet fresh water, the surrounding waters offered up piles of seafood and shellfish, and tidal marshes supplied quantities of salt for preserving meat and fish. The deep, protected waters of Milford Haven offered an ideal alternative to the official ports of entry, Urbanna and Yorktown - thus to avoid paying British duties. “The island’s strategic location afforded opportunities to transact maritime business without going into the official ports,” Wrike says. “References made to ‘warehouses’ on Gwynn’s Island attest to the volume of trade handled there.” Milford Haven was also a fine shipbuilding location, and by the mid-1700s, Gwynn’s descendants and others who came here were launching schooners, snows and brigs used in the West Indies trade.

    While deciding to leave Hampton Roads with his fleet of British loyalists, Dunmore also considered relocating to Yorktown, Urbanna or the Eastern Shore, but chose Gwynn’s Island, at least partly because of its shipbuilding, freshwater supply and trade location. On May 27, 1776, at four o’clock in the morning, 100 Royal marines from Dunmore’s fleet landed on the island, and by dawn more than 700 British troops were ashore.

    Dunmore spent the next several weeks fortifying his encampment and engaging in political skirmishes with Williamsburg. But by early July, Virginia forces under Brigadier General Andrew Lewis were gathering to oust Dunmore. Their offensive - known as the Battle of Cricket Hill, where the Americans had established fortifications on the mainland - began on July 9 on a low tide at dawn, when Lewis personally aimed and fired a cannon at Dunmore’s eponymous flagship guarding the narrows. The cannonball smashed through Dunmore’s cabin in the stern, killing his sailing master. “At the same time, the other American battery opened fire on the camp, Fort Hamond [a British fort just east of the narrows], the fleet and the Dunmore. The cannonballs flew across the fort and mowed down tents,” Wrike says. “The inexperienced troops and newly recruited loyalists became panicked and confused. No one had anticipated the American attack.”

    The loyalists crumbled. The next morning, Dunmore and his officers fled for St. Georges Island (on the Potomac) where they planned to regroup. Dunmore eventually sailed to New York and then England, where he plotted to retake Virginia until his death in 1809.

    On Gwynn’s Island, life and trade slowly resumed. By the mid-1800s, Elizabeth Ellen Hill had moved with her family from New Hampshire to 350 acres on the southeastern end of the island. Under the pen name May Evergreen, Hill wrote articles called “Chimes from the Chesapeake” for a Boston publication, revealing insights about life on the island at the time. She provides a lively description of the convoluted steamboat trip required to reach the island; passengers would leave on a boat from Baltimore at 5 p.m., sail all night, stop in Norfolk, change boats, “and if the ‘lady mother’ be in a wrathful mood, she will toss you about in that small boat called the Coffee, in a style very irritating to you innermost.” The Coffee would put in at Mathews Courthouse. From there it was a short trip by land to Cricket Hill, where a sailing canoe would take passengers across the narrows to Gwynn’s Island, at last.

    There, Hill says in a description that could be written today, you would find fertile soil, a fine climate and magnificent woods. “These woods are my admiration and delight,” she wrote. “The trees are large and lofty with no underbrush to obstruct the pathway of us strollers; and then they are constantly singing to me with sweetest melody; the soft sighing of the pines seeming but as an echo to the deeper tones of the restless Chesapeake. There is an abiding sense of quietness pervading the atmosphere around our ‘island home.’ We are far removed from the din and bustle of the world.”


    It’s early morning down at Callis Wharf on Milford Haven - where the steamboats once put in, and for years the bustle of workboats never seemed to stop. Only a few workboats are here now. All is quiet and will remain so, until a pickup truck with the license plate isldboy wheels into the parking lot, John Raymond Bassett walks down to his pound-netting boat Pet, fires up the engine and heads out. For the 33-year-old Bassett, once virtually deaf, quiet was not really a good thing until last year. His story tells a great deal about Gwynn’s Island today and the people who live here.

    When he was seven years old, Bassett contracted a severe case of measles which left him almost entirely deaf. He tried hearing aids of various types, but nothing really worked. At age 12, his father - a tugboat captain and self-employed carpenter - bought him a skiff and about 50 crab pots, and Bassett, like so many other island boys, started working the water. He stopped long enough to attend college and get a degree in graphic communications, and for a time he worked for a local newspaper. “I couldn’t stand it,” he says. “What I’m doing right now - fishing - it’s hard to leave that. It’s not rewarding money-wise. But if you truly love something, it’s not hard.”

    Bassett had given up his dream of following his dad to sea on a tug (the Coast Guard wouldn’t license him because of his hearing loss), or of becoming a Navy pilot. But a few years ago, a cochlear implant became a possibility. “I realized I wanted to do something with my life,” he says. “I wanted to hear again.” The surgery was quite expensive, and his wife’s medical insurance wouldn’t cover it. So the people of Gwynn’s Island and Mathews County raised it - bit by every bit. Churches, civic clubs, the fire department and rescue squad - all held various fundraisers and fish fries, eventually coming up with about $40,000. “It was so much, what they did,” says Bassett. He laughs, “I guess they were tired of having to repeat themselves five times.”

    In April 2002, Bassett had the surgery, and over time he has learned to talk - and to hear - all over again. He leans his thick forearms on the picnic table on the dock, his red beard flecked a bit with white, and shakes his head in wonder at it all. “I can hear the seagulls screaming and hear the fish hawks. To hear them . . . wow,” he says. “When we’re getting the fish up, the seagulls get all around and it’s just like the choir singing almost.”

    This is not an easy life. Pound-netting, Bassett tells me, has been difficult and mostly unprofitable for the last couple of years. But leaving this island where he grew up, where so many people backed him, is not negotiable. “It’s like my wife says, I’d die if you took me away from here,” he says. “There’s always been a strong sense of community here and it’s something I hope we never lose.”

    Clearly, times have changed profoundly on the island. Captain Stewart Edwards, whose family on Edwards Creek is one of the oldest here, remembers how dozens of Crisfield boats would anchor at Hole in the Wall, waiting to buy fish. “In the twenties and thirties, they were pound fishing,” Edwards says. “That was the best time I guess here for the fishing.” Edwards and his father built a marine railway - just to repair their own boats, rather than wait the weeks it sometimes took the only other yard on the island. Today, Edwards’s son Bobby now runs R.S. Edwards and Sons Marine Railway, while Bobby’s twin, Sammy, works on a tugboat.

    Just down the creek from the railway, I hop aboard a 25-foot Grady-White owned by John H. Tobin Jr. and his wife Mary Call Tobin. Like many residents, Mary and her sister, Cricket Call, grew up elsewhere but have known the island all their lives, because their father, a Richmond doctor, would come here to fish and hunt. Now, both sisters are permanent residents. And Mary still loves to fish. “My favorite spot is the Cell - if we can get past the tautog holes,” she says, as we motor toward Hole in the Wall. “They’re awful tempting.”

    The Bay has eaten away at the island’s southern edge at Hole in the Wall; John Tobin recalls how he used to be able to drive nearly all the way down the island’s eastern beaches to the inlet to go duck hunting. Now, the Bay has perforated the tip of the island with cut-throughs, creating a series of islets that are slowly slipping into oblivion. “The sand is shifting constantly,” he says. “I don’t think it’s going to be much more than sandbars in a matter of time.”

    More than likely true. But there’s far more to Gwynn’s Island than shifting sand and the slow hammering of time. The breeze in the pines has romanced generations here, and if a community’s pure love for a place can be any kind of an anchor, Gwynn’s Island will endure.