Gary D. Crawford - February 2011


The Winstone Riddle
Gary D. Crawford


When the great adventurer and explorer Capt. John Smith came up the Chesapeake in 1608, he was seeking riches, searching for a passage to India, and trying to get the lay of the land. He also may have been looking for some time away from the squabbling in Jamestown. It had been a rough winter.
Smith’s two voyages that year were astonishing feats of surveying, for the map he produced in 1626 is remarkably accurate. The size and shape of the Bay, and the major features of the western shore, were known at last. Many later maps weren’t nearly as good.
Naturally, those of us who live along this part of the Eastern Shore are rather disappointed that he never came here. But just as he missed the mighty Potomac on his first time up the Bay, he also missed the largest river on the Eastern Shore. Each time he passed by, up and back, up and back, he didn’t recognize the four-mile-wide mouth of the Great Choptank River for what it was. We should remember, however, that it was the western shore he was scouting, checking every river and creek for an opening to the west. Each river- mouth or bay, every break in the western shore had to be explored. It might be the fabled Northwest Passage!
Having explored Delmarva down south, Smith knew it was the landmass that actually forms the Bay by separating it from the Atlantic Ocean. The Northwest Passage could not be over here—wrong ocean. So, after examining the western shore and the northern reaches of the Bay in some detail in the summer of 1608, Smith returned to Jamestown.
Looking off to the east, Smith would have seen the Eastern Shore in the distance as a dim line of forest and that is how he represented it on his map—as a vague, wavy shore line in front of a mass of trees he named Brooke’s Forest. Undoubtedly he noticed the shoreline receding from his view at some points, even disappearing, while elsewhere it appeared closer—evidence of various bays and headlands. He may have tried to indicate some of this with the breaks in his wavy line. There is no evidence, however, that he knew anything about what lay beyond the two largest openings—Eastern Bay and the Great Choptank River.
Still, Capt. Smith was no casual passerby. He was a sharp observer, an experienced surveyor, and a skilled map-maker. Had he known anything of the Eastern Shore other than it was thickly forested, we can be sure he would have put it on his map. Consequently, we can be virtually certain that when Capt. Smith passed by Talbot County he was miles away, far out in the Bay. Those of us who have come out of the Bay looking for Knapp’s Narrows on a hazy August afternoon know just how close one has to be to make out any details of our shoreline. Imagine it with no buildings or landmarks! I am fully prepared to forgive Captain Smith for these two major features he didn’t see.
Smith did, of course, see something off to the east—something in front of that vague line of trees. He saw (or thought he saw) three islands there, apparently quite clearly and distinctly, for he drew them as such and placed them prominently on his 1626 map. He even called them islands, naming them “Winstone’s Isles.” (I have numbered them here for convenient reference.)
Note that each Isle is drawn completely and in the round. Whatever they really were, Smith believed that Winstone’s Isles were off-shore islands, wholly detached from the mainland. Beyond the Isles to the east can be seen that vague broken line representing what Smith could see of the heavily forested mainland.
He could have been wrong, of course.
This is where our the riddle begins. No one has used the term “Winstone’s Isles,” before or since. So what were they? Or rather, what are their names today?
If we take a look at a modern map, the riddle seems easy. Why, there they are! Winstone’s Isle #1 obviously is Kent Island, Isle #2 is the Talbot County mainland (Bay Hundred), and #3 is the Dorchester County mainland (the Cook’s Point headland).
Here’s the problem with that theory. We’re looking down from above. The mapmaker knows what’s behind these headlands, the fact that Kent is and Bay Hundred almost is an island. Smith didn’t know any of that because he was looking at things from water level, without any idea of what lay beyond his field of vision. He didn’t explore this part of the Eastern Shore, didn’t peek into Eastern Bay or the Great Choptank River. In other words, he couldn’t have known anything about the geography of Talbot and Dorchester counties. He didn’t even know that Kent was (just barely) an island.
All Smith knew about the Eastern Shore was what he could see from well out in the Bay, namely a vague shoreline in the distance, with indentations, or maybe gaps, in front of a vast forest. And that is precisely what he put down on his map – a vague wavy line with gaps here and there, the edge of a woodland he named Brooke’s Forest.
Out in front of that forest, well and clearly offshore, stand three distinct islands. Could they be headlands or peninsulas rather than islands? Well, they could be, but Smith didn’t think so. After all, he named them Winstone’s “isles” and drew their entire shapes. Smith did not invent things. His distances and shapes may have been faulty at times, but he would not have described these objects as islands unless he could see more or less all the way around them.
So the modern map is profoundly misleading. Take out what we know but Smith did not – Eastern Bay and the Great Choptank – and you are left a map like this, with a shoreline something like the black line. All that water to the east of the line was unknown, never seen by Smith. We must replace all that water with forest. Remember, there is nothing remotely like our flooded coastline on the western shore, which Smith did explore in detail. The black line here represents Smith’s wavy coastline behind the islands and in front of the forest, the one with a few gaps that might have been openings.
But if that black line is the shore as Smith saw it, then all of Winstone’s Isles seem to disappear! West of that line is nothing but the open Bay. Where did the isles go? Or rather, what could Smith have seen out there?
In his excellent book The History of Maryland [1879], John Scharf makes the same mistake, confusing what we know with what Smith knew. Scharf writes: “The most northern of “Winstone’s Isles” exactly corresponds to [Kent] in situation, lying southeast of the mouth of the… Patapsco, opposite the mouth of the Severn…and nearly south of Swan’s Point…. An indentation and break in the coast-line also mark the mouth of the Wye [Eastern Bay], which Smith did not explore” [My emphasis].
Then, having convinced himself that Winstone Isle #1 must be Kent Island, poor Mr. Scharf goes looking for two other objects, lying in a row to the south and of about the same size. There are no such objects, of course, but no matter. Contradicting what he has just said about Smith not exploring the area, Scharf jumps to this convenient but unlikely conclusion:
“[Smith] clearly mistook the deeply indented peninsulas of Dorchester and Talbot counties as islands, which, with Kent Island, form the three islands he calls ‘Winstone’s Isles.’ Nothing could be more natural than that he should mistake the peninsulas of Talbot and Dorchester for islands, as they are connected with the mainland by narrow necks, and deeply indented with bays, and the errors could only have been avoided by coasting all along their shores.”
Well, hardly. Since he did not explore the mouth of the Wye (or anything else in Talbot County), how are we to imagine that Smith & Company — rowing along five miles out in the Bay — received intelligence about all those deep indentations and narrow necks? That seems more supernatural than natural.
No, Scharf can’t have it both ways. If Smith had explored these two counties, he would have known they were not oval islands and wouldn’t have drawn them as such. If he didn’t explore them, as Scharf admits, then Smith had no reason to have imagined them to be islands. Besides, can we completely ignore the coastline that Smith clearly shows behind Winstone’s Isles? No, the logical conclusion is that Talbot and Dorchester are not Winstone’s Isles #2 and #3. And that casts real doubt about massive Kent Island being Isle #1.
Whatever Winstone’s Isles were, Smith saw them as islands and depicted them as such — modest-sized ovals, evenly spaced, and all standing well out from that coastline Smith could make out, dimly, in the distance. But what could they be? What did the Captain see?
An earlier historian, John Bozman, did rather better than Scharf, I think. In his 1837 book, The History of Maryland, Bozman wrote:
“…the whole of the Eastern Shore of Maryland, from Swan-point in Kent county to the lower part of Dorchester county near to Limbo, is skipt over by [Smith] without notice. His delineation, on his map, of three large islands, called by him—Winstone’s Isles, represented by him as being nearly of equal size, and stretching along the Eastern Shore from Swan point to an indentation of the shore, which we may suppose he intended for the Choptank river, demonstrates, that in both his excursions up the bay, he kept close to the Western shore, without minutely examining any part of the Eastern below the Tockwogh. Hence the Isle of Kent must have been entirely unknown to him, or considered by him as main land” [My emphasis].
That’s really quite good, isn’t it? Because the Eastern Shore was “skipt over,” we can be sure that the observant Capt. Smith didn’t come anywhere near us. The identity of Winstone’s Isles puzzles Bozman, but, to his credit, he doesn’t leap to conclusions. He recognizes that Smith might not have known whether Kent was an island. (Actually, before the digging of Kent Narrows, the island was connected to the mainland by a marsh, called by the Indians “the Wading Place.”)
Our friend Scharf pounced on Bozman, writing “How the careful Bozman, with Smith’s map before him, could say that ‘the Isle of Kent must have been entirely unknown to him,’ is surprising.” Sorry, but I have to call a foul here. Bozman didn’t say that Smith didn’t see Kent Island. What Bozman said was that Kent might have been “considered by him as main land,” a phrase Scharf somehow forgot to include in his quotation. What Bozman meant (and should have written) is that Smith didn’t know that Kent was an island. And that is true.
Bozman’s only mistake was not to follow his own logic and recognize that Kent cannot be Winstone’s Isle #1. Lacking any knowledge of the Eastern Bay and Kent Narrows, Smith had no reason to imagine Kent to be an island. Yet Smith’s map makes absolutely clear that Winstone’s Isle #1, whatever it was, definitely was an island.
Bozman suspected that Winstone’s Isles were to be found somewhere among the smaller islands. On page 115 he writes: “...the three islands, therein imperfectly sketched by him, as lying opposite thereto, called by him ‘Winstone’s isles,’ must have been the isle of Kent, Poplar, and Tilghman’s islands, but most inaccurately designed.”
Bozman is so close. Of course, Tilghman’s Island cannot be any of Winstone’s Isles, and Scharf was right to smile at that suggestion. Only a very sharp-eyed mariner who spots the entrance to Knapps Narrows, enters it, and follows it through to Harris Creek can know that Tilghman’s Island is an island. Why, one wonders, did Bozman not include Sharp’s Island in his list of possibilities? If Poplar is a possibility for Isle #1, than Sharp’s is a much better candidate than Tilghman’s for Isle #2. It is similar in size to Poplar, lies a few miles directly south of it, stands well offshore. In Bozman’s day, it was in plain sight.
At least Bozman did not try to transmute counties into islands, as Scharf tried to do. And he should have had more faith in Smith’s skills of observation and cartography, for Winstone’s Isles were not so “inaccurately designed” as he said. I have a hunch that if he could have put Kent Island out of his mind once and for all, Bozman would have solved the riddle.
We must be charitable, however. Even modern historians seem unable to drop Kent Island off the list of candidates for Winstone’s Isles. My friend Edward Haile, in his otherwise scrupulous 2008 analysis of Smith’s voyages up and down the Bay, got into difficulty here. Convinced that Kent must be Isle #1, he brushes all the smaller off-shore islands aside as being too small. Having ruled them out, he has to rule something else in. Guess what? He picks up Scharf’s old argument about Talbot and Dorchester peninsulas somehow looking to Smith like islands. Ed and I argued this out one day in my bookstore, the Book Bank on Tilghman’s Island. Terrance Smith, formerly a reporter on the PBS News Hour, acted as referee. Terry formally, and courteously, ruled the debate a tie. (But he said I won.)
“Talbot” is not an island. More important, it doesn’t look anything like an island from water level in a small boat miles out in the Bay. If you know all about Eastern Bay and the Great Choptank River, then you might suspect it to be an island, but Smith knew nothing about those bodies of water. The same is true of the Dorchester shore. Cook’s Point isn’t a point if you don’t see the Great Choptank River — which Smith didn’t. No one passing down the Bay could possibly represent either county on his chart as two smallish oblong blobs. Whatever they are, all three of Winstone’s Isles are oval objects of similar size that stand in front of the coastline.
If Kent, Talbot and Dorchester all fail because they are too big, don’t look anything like islands, and can’t been seen to be connected by narrow necks unless you go around behind them — which we know Smith did not do – what, then, could Winstone’s Isles possibly be? Did Capt. Smith simply make them up just to fill in a blank on the map?
Now hold onto your hat. Here’s the astonishing thing. Pick up any map of the Bay from 1900 or earlier, and there they are!
Winstone’s Isles are there just as plain as day. No kidding. You don’t have to squint or twist the map around or turn counties into islands. They are just where Smith placed them on his map in 1626 — three objects standing right where they couldn’t be missed by a passing mariner and far enough offshore to reveal the water behind them. In other words, they are islands. They even lie in a neat north-south row. The northern and middle ones are about the same size; the southern one is a tad smaller. Each is a rough oblong.
Don’t believe me? Take a look at this map, published about 50 years after Smith’s.
Note that by 1671, Kent is recognized as a large detached island, even if Bloody Point is shown inside Eastern Bay pointing at St. Michaels. The Little Choptank is shown in Dorchester, but somehow, despite Talbot County being fairly well settled by this time, the Great Choptank does not appear.
Still, there are Winstone’s Isles, clear as a bell. Do you see three blobs in a row? I do. And they’re just where Smith placed them.
Here are some later maps.
Those sure look like Winstone’s Isles to me, lying there in the shallow waters off to the right of the ship channel. I presume you know what they are called today.
Riddle solved! Not so hard, after all. 1-2-3, all in a row. Poplar, Sharp’s, and James.
And what’s the problem with these three being Winstone’s Isles? Absolutely nothing.
All three islands are different now, of course. James is washing away, Sharp’s is gone entirely, and Poplar is being rebuilt. It’s true that James Island wasn’t really an island in 1608 and if Smith had rowed over for a close look he would have seen that. But he didn’t row over. Smith was headed for Calvert Cliffs, miles across the Bay. Then (as now) James stood well out in the Middle Bay with lots of water all around it. It’s called James Island for a reason. It truly looks like an island.
So, let’s take one last look at Smith’s 384-year-old map, oriented with north to the right as he published it, and compare it with a 1920 Talbot County map.
Not bad, Smitty. You even spotted Chessie, the Sea Monster.
Just one thing still puzzles me about this: Who the heck was Winstone?