Issue: From the Chesapeake Bay Magazine Archives
Destination: Gwynn's Island

A long-awaited journey to Gwynn’s Island gives the author the chance 
to retrace the steps of the most famous Gwynn’s Islander and get 
acquainted with this island out of time. Now, he wonders, did Lord 
Dunmore have to get there through the Hole in the Wall too? [August 2013]

By Paul Clancy
Photographs by Jay Paul

It was first light when my sailing friend Purnell Delly and I departed Salt Ponds Marina in Hampton and raised our sails just as the sun blasted through an ironclad sky. It was early June and great to be on the lower Bay again. As we passed the enormous, yawning mouth of the York River I realized—standing forward of the mast—how wide the Bay is here, how the land drops away and I could swear I was out on the open ocean.

And I could imagine a certain fleet of British ships on another dawn—the dawn of independence. Like them, we were headed to Gwynn’s Island, a daunting, eagle-head-shaped outpost on the shores of the Piankatank River.

I’d never been to Sir Hugh Gwynn’s lovely retreat before, possibly because I’d heard the approach was, well, interesting. And as it turns out, I’d missed out on some fascinating people, amazing—really amazing—history, great food and sublime vistas.

I could just take the easy way into Gwynn’s—that of the up-and-around-the-long-way variety. But first, I wanted to try what seems the most logical approach—through the infamous, confusing series of markers and channels known as the Hole in the Wall. You simply arrive on a rising high tide and pick your way through . . . right? Sure you do. But I wasn’t about to do it alone. And so it was that Purnell and I left Norfolk on a Saturday afternoon, headed first for Salt Ponds Marina. It was going to be about a five hour sail and we wanted to make the attempt before noon on Sunday.

I should have known, or at least suspected trouble when I called Jean Tanner, director of the Gwynn’s Island Museum, and told her how we planned to get there. “Oh, that’ll be interesting,” she said. Hmmm. Just because the charts show three different marker protocols, with reds suddenly shifting to green, and numbers changing like slot machines, that’s no reason for concern. Is it? Bring it on, we thought. 

But then, as we cleared the first set of markers, there seemed to be a mystery red channel marker that exists on none of our charts. So be it. We steered to its left, trusting its truthfulness. 

“Is that the depth under the keel?” Purnell suddenly asked, nodding toward the depth sounder. “No, that’s the actual depth,” I said, realizing at the same second that we’d suddenly run out of breathing room. Right where it should have been seven feet, our three-foot-draft full keel kissed the bottom once, twice and then found it. We raced the engine a couple of minutes, bounced some more and then backed all the way to the previous marker.

“This bottom is organic,” Purnell said, “constantly in flux.” We lost our nerve then and there and turned back out to safe water. “Parts of the island’s shoreline seems to be only a couple of feet deep a quarter mile offshore,” he said, peering at his smart phone chart display. “After a vicious assault by a nor’easter, it has to be transformed!”

So we went the long way after all, north around Gwynn’s Island, then entering the harbor via the Piankatank. No problems there. Soon enough an accommodating swing bridge tender gave us an opening, and we were in lovely Milford Haven, eagerly anticipating our next adventure—the Seabreeze Restaurant. I’d heard that you can pull right up to a public dock beside it, and after calling to make sure of the location, we docked there in plenty of water. 

Within minutes, it seemed, we were at a corner table, with sweeping views of the harbor and downing glasses of iced water. Obviously a favorite local spot, the Seabreeze was buzzing with the chatter of local families on a Sunday afternoon. The service, the fried flounder, baked beans and stewed tomatoes couldn’t have been better. 

Because it was choppy in the haven, we decided not to anchor out, instead motoring across to Morningstar Marina where we tied up to an outside berth. The marina, on the Mathews County mainland, is dominated by a vast boatel with more than 250 berths stacked three high. But there was something else we discovered while walking to the office: a cannon and earthworks facing the island. It was, I realized, what remains of the famous Fort Cricket Hill. This is where Lord Dunmore, the last royal governor of Virginia, met his comeuppance.

A little patriotic music here, please, while I tell you about John Murray, said royal governor and the fourth earl of Dunmore. It was late 1775 and revolutionary fervor was in the air, and he didn’t like it one bit, coming down hard on troublemakers. Which only spurred them on. Patrick Henry and others forced him to flee from Williamsburg to Portsmouth on his ship. There, in the company of Andrew Sprowl, founder of Gosport Shipyard—later Norfolk Naval Shipyard—he nursed his injured pride and plotted revenge. He also issued a proclamation promising freedom to slaves who’d fight for him, putting together what was to be called the Ethiopian Regiment. They proudly wore uniforms with “Liberty to Slaves” embroidered on their breasts.

But with more brio than sense, in early December Dunmore sent his forces against well dug-in patriots at Great Bridge on the Southern Branch of the Elizabeth River. And got his butt kicked. Badly. 

Dunmore, along with his wife and several local Tories, including Sprowl, then took refuge on his ships in Norfolk Harbor. There were dozens of vessels with him, packed with all manner of folks, from British marines to loyalists to black soldiers. Many were starving and racked with smallpox, and after local forces refused to help or provision them, Dunmore and his ships bombarded Norfolk. Fires broke out on the waterfront, and then patriots did the rest, burning the city just about to the ground to keep the British from quartering there. Thomas Jefferson would use this for propaganda purposes—you remember the litany against King George, “He has plundered our seas, ravaged our Coasts, burnt our towns, and destroyed the lives of our people. . . .”

Dunmore was apparently fearful for his life and those of the other souls stranded on his vessels. There were daily reports of bodies being dumped in the harbor. But there was one ray of hope. Reports reached him of a place called Gwynn’s Island 40 miles up the Bay with plenty of fresh water, an excellent harbor and, maybe best of all, many friends of the Crown. 

Once called Pyankatank Island by the Indians, it had been settled by Sir Hugh Gwynn in about 1610. His descendants were now among hundreds of colonists and slaves on the island—a port in an ominous revolutionary storm. So in May 1776, the royal governor and his retinue of about 2,000 soldiers, marines, loyalist friends and hundreds of members of the Ethiopian Regiment arrived in ships and invaded the island. They plundered it for every last scrap of food and timber, built redoubts along the shore and hunkered down for what they assumed would be a long visit. True to form, the puffed-up Dunmore dismissed a force of Patriots gathering across the harbor as mere “crickets.” 

But these patriots secretly built up quite a battery, including two 18-pounders, two 16-pounders and five 9-pounders, keeping them out of sight by day. Meanwhile, advanced cases of smallpox were taking a ferocious toll on the invaders, including Sprowl and hundreds of soldiers. A large contingent of royal marines, sent to the mainland for provisions, failed to return. 

One report I’ve seen says that in the midst of all this, Maryland’s last royal governor, Robert Eden, arrived at Gwynn’s Island from Annapolis in his ship, HMS Fowey. He had lost power years before and, finally, in late June of 1776, was allowed to leave peacefully. He set sail for England, but apparently stopped for a visit with Dunmore. He mustn’t have liked what he saw because there are no reports of his lingering. 

On July 9, learning of the Declaration of Independence, the patriots brought their battery out of hiding and opened fire. The very first shot is said to have hit Dunmore’s flagship, injuring the governor and killing his boatswain. And, just like that, the one-time royal governor, fearing an amphibious assault, gathered what was left of his followers and set sail for New York, leaving untold numbers of hastily dug graves on the shoreline. 

But the evidence of history on Gwynn’s Island goes back a lot further than Dunmore or even Sir Hugh, back to the dawn of civilization. And that was the other part of this trip that was so interesting to me. 

I had called ahead to Jean Tanner, who put me in touch with John Dixon, a retired engineer who has compiled a history of Gwynn’s Island and a study of black settlement on the island. Much to our luck, he met us at the marina and gave us a brief tour on some of the island’s few miles of paved roads. 

A week later, Barb and I would arrive with bicycles and take a proper look around. There isn’t a town per se, unless you count a central square where there’s a volunteer fire station, a Baptist church and the civic league offices. Riding along Cricket Hill Road from the restaurant, you get a sweeping view of the Piankatank and white sails out of Fishing Bay. At the opposite end of the island, at the end of Route 633, there are sandy beaches facing the Bay.

We’d ride down to the end of Callis Wharf Road, too, where there’s still an active seafood company. We’d meet a man and his grandson fishing off the pier and hear him say, no, he didn’t reckon you could navigate Hole in the Wall without someone local to guide you. He’d been there all his life, he said, and never understood why the tide floods into Milford Haven from the Piankatank and not from the Bay.

Dixon, a passionate historian, had done a study of the island’s black population, including families of former slaves and descendants of Dunmore’s regiment. But by 1930, he found, the blacks had simply vanished, possibly because of the lure of shipbuilding jobs elsewhere or a declining fishing industry. Gone too were any traces of people named Gwynn. Apparently, they would not have been welcomed back because of their hospitality to the British. 

Dixon drove us to the museum in the middle of the island, where we met Jean Tanner, her husband Bob, and docent Pat Kurovics. And what an amazing little museum it is! The former Odd Fellows Lodge, school and grocery now has two floors packed with artifacts of Gwynn’s Island and Mathews County history, including Indian arrowheads, eyeglasses and English pottery that probably dates to Dunmore’s occupation. There’s even a statue of Sir Hugh.  

One phenomenon that swells the collection is the storms that typically rake the island, churning up long buried treasures. “It’s so much fun living here,” Jean said, “because you just don’t know what’s going to happen with the next storm.”

One thing that happened 35 years ago was that Bob Tanner was walking on the beach near their home. It was nighttime and low tide. And there in a small pool of water glinting at him was a beautifully fluted projectile point that has been estimated to be 13,000 years old. Such “Clovis” points, so named because of an early discovery in Clovis, N.M., were considered evidence of Siberians migrating across the Bearing Strait to Alaska, then fanning out across North America. But recent discoveries of these points on the east coast have prompted a rival theory: that other migrants came across an ice bridge from Europe. 

When he found it, Bob realized, “I’m holding something in my hands that hasn’t been touched by anybody for ten thousand years.” Near the display, almost as a casual afterthought, is a mastodon tusk. Astonishing, I thought. I could and did reach out and touch it. 

At this point, the memory of something else about this amazing museum sort of tapped me on the shoulder. Opposite the Clovis point case is a display about what could be the oldest known handmade tool in the Americas. It was found in 1970 by a Mathews County fisherman while dredging in the near Atlantic off Cape Charles. What he pulled up was an ivory mammoth tusk, a large molar and a bi-faced stone blade. The objects made their way to the museum but weren’t dated until a few years ago when a Smithsonian Museum archaeologist happened to see it and called his boss. “You’d better come down right away,” was the gist of the message.

The boss, Dennis Stanford, curator of the Paleo-Indian Program at the Smithsonian’s Natural History Museum, borrowed the objects and put them through two years of carbon dating, x-rays and DNA tests and concluded that they are 20,000 years old. They bolstered his thesis, published in a new book, Across Atlantic Ice: The Origin of America’s Clovis Culture, in which he makes the case that people from northern Spain made it across to our shores 14,000 to 25,000 years ago.

The display now showcases exact replicas of the items (the originals are destined for the Smithsonian), but they sure put little Gwynn’s Island Museum on the map. “This little island has made history,” Pat Kurovics exclaimed.

There was way too much to see in the few hours we had, but one other thing struck me with a jolt. Upstairs is a storyboard about Charles Edwin Respess, a onetime lighthouse keeper who in 1915 was sailing from Windmill Point to Hole in the Wall in a small boat. A sudden storm caught him in shallow water and broke his mast, leaving him at the mercy of heavy breakers. The next morning, the 52-year-old keeper’s body was found close to a Gwynn’s Island beach. Yikes, that’s all I needed to know about that approach. 

Purnell and I wanted to stay longer, to get a good look at the rest of the island, but heavy weather was expected the next day and we decided on an early departure. Lucky for us, we were able to dodge a couple of nasty squalls and make it back to Salt Ponds just ahead of a torrential downpour. 

Our two days on the water were sweet but much too short. But at least we’d done it—sailed to one of the best-kept secrets on the Bay, sojourned in its lovely harbor and touched the surface of history as deep as a bottomless quarry. Perhaps, if we don’t try its eastern approach again—and if we can prove we don’t have relatives named Gwynn (just kidding)—the island will invite us back.