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Original Issue


There is a colonial charm about the quiet villages and sprawling farms that border the Chesapeake. On these pages a famous yachtsman describes the endless variety of cruising waters in the bay's upper reaches

It was blowing a gentle little southerly, a final breath of summer, as Finisterre ambled across Annapolis harbor. The sky was blue, very blue, dappled with small clouds, the sky of a warm October afternoon, yet in the shadow of the mainsail a chill was in the air. Along the banks of the Severn the yellows and reds of fall accented the lingering greens.

I stood in the cockpit, leaning against the mizzenmast. Occasionally I touched the spokes of the steering wheel with one foot, half dozing in the autumn sunshine, reflecting on the ease of cruising as opposed to the tension of racing: of getting up in the morning not knowing where I am going, maybe waiting for the wind to decide for me, not caring if the proper jib wasn't set; leaning back at evening over an anchor-down drink; falling asleep at night hugging the thought there would be no urgent summons from deck....

"Hey, skipper," said Bill McWilliams, breaking into my reverie. "The jib's soft. Wind's come ahead. Shall I trim?"

I looked at the masthead fly, then at the making wavelets, splintering the sun shafts into glittering points. As so often happens in fair weather, the breeze was advancing with the clock: it had been mirror-calm at sunrise and through the early hours. The first cat's-paws appeared around 10, as we had gotten under way. Now it had freshened to good steerageway. Later, if it followed the usual cycle, it would strengthen through the afternoon, perhaps working up to a rousing, rail-down wind around 4, to taper off at sunset to a night of sibilant whispers in the treetops.

Having gotten no answer about the jib, Bill strolled aft. "Where are we going, by the way?"

"I dunno," I replied lazily. "I haven't given it much thought."

What I really meant was that here on the Chesapeake there were so many delightful prospects I hadn't been able to choose. The whole area is such a lacy pattern of creeks and bays and rivers that it is hard to decide whether it is water bounded by land or land bounded by water.

"Any suggestions?" I asked Bill.

An old Chesapeake hand, Bill squinted at the sky. "If we go anywhere down the bay," he mused, "it will be a beat to windward. If we go up, we'll be reaching." He sat on the cabin top and sprawled his legs across the lifelines, thereby casting a vote for sloth. He looked so comfortable I flipped on the automatic pilot and went forward to join him.

Harbors literally lay in all directions. Even if we chose to turn around and sail west, up the Severn River instead of continuing into the open bay, we could pick from a multitude of anchorages, as the Severn is typical of Chesapeake tidal rivers, although it is a lesser one by bay standards. On its southern shore, even before you get to Annapolis, there is Back Creek; then Annapolis, lying between Spa and Dorseys creeks, then a ladder of creeks; each a good anchorage: Weems, Luce, Saltworks, Chase, Clements, Brewer, Forked. Then the Severn broadens to Round Bay, a body of water large, open and deep yet wholly sheltered, with Little Round Bay off its western side and Little Round Bay Creek beyond that. And still farther west the Severn continues another two miles, past other creeks, to end finally in another bay large enough to have its own sailing club. Thus almost every Chesapeake tributary must be thought of as a microcosm of an infinitely varied cruising world.

When the radio towers on Greenbury Point dropped astern there came a moment of decision. I let the wind suggest, gradually turning the bow to leeward until finally Finisterre slanted diagonally across the bay, almost toward the northern tip of Kent Island.

"Heading for the Chester River?" inquired Bill, still sprawled on deck.

"Guess so," I answered. "If we come off for Gibson Island the wind will be dead aft. We'll have to set a spinnaker or start the engine to stem the tide."

Perish either thought. Discussion complete. Master and mate in accord. Bubbles slid along the hull and traced our wake, water furrowed by generations of ghostly ships. Where Finisterre now moved, Indians once had passed in crude, hollowed logs. Captain John Smith sailed by in 1608 to "perform his Discovery." Haifa century later Edward Lloyd of Wye House appeared in the first yacht, "a pleasure boat of 60 tons burthen," complete to "Ensign and pennant with 15 stripes, arms painted thereon, the field azure, the Lion gold...and six brass guns fixed on swivels to act in such a manner as to give the greatest report." And here also had passed each development of the age of commercial sail: the Chesapeake log canoe, the pungey, the ram, the bugeye, even the Baltimore tea clipper.

As we drifted, I reflected on another of the charms of cruising: that every area takes its character from the life along its shores, both present and past. The Caribbean, the South Pacific, the Aegean, the Baltic, the Mediterranean—each is different because of its own combination of geography and history.

The Chesapeake, too, is unique, as I was rediscovering. Here is a land of graciousness, of easy living, a legacy of cotton and tobacco and a plantation life when visits were measured in weeks and it was necessary to pass legislation requiring that slaves not be fed terrapin too often. Here a small cruising yacht drifts across stretches of water bordered by trees or open fields, with perhaps an occasional glimpse of a lovely old house on a point. Here are anchorages disturbed only by the singing of birds and spreading rings following the splash of jumping fish. In the quaint, small villages people are hospitable and friendly. In many ways, on the shores of the bay today exists one of the nearest approaches to life on the other side of the Atlantic—a reasonable facsimile of rural England modified by terrain and time.

As I mused, the breeze freshened and Finisterre leaned to it and spurted ahead. Gone was introspective ease, to be replaced by the exhilaration of motion. Cruising is like that: a matter of mood stemming from weather and circumstance. Now we wanted to feel the boat go. The main was slacked a hair, the jib trimmed a few clicks and Finisterre boiled along with the wind on the quarter, all hands awake to the perfection of the moment.

Love Point lifted rapidly. Swinging around the squat lighthouse marking the end of the shoals beyond Kent Island, we came hard on the wind. A beat could have been avoided by reaching a few miles to the fishing village of Rock Hall, or Swan Creek beyond. But now we felt a little windward work might not be amiss. "It will make us feel we've earned a drink," opined Bill bravely, not forgetting the distance was short, the water smooth and that sail could be easily reduced.

Rail down, Finisterre drove across the river. Contrary to a misconception about Chesapeake cruising, the boat was in no danger of running aground—if her crew did not go completely to sleep. True, there are many areas of the bay where the water is spread thin, but in general the major tributaries of the Upper Bay—local name for the part north of the Potomac River—offer ample depths. Following normal pilotage procedures, a boat with six or seven feet of draft has no real problem. Navigational aids are plentiful, fog infrequent, tidal range and current velocity slight, and the bottom is not rock but mud—lovely soft mud, so grounding is an inconvenience, not a catastrophe, just as a centerboard is a convenience, not a necessity.

Thus on Finisterre we had no navigational cares; and ahead the Eastern Shore stretched away as a flat peninsula 136 miles long, dangling between the Atlantic Ocean and Chesapeake Bay. It is shaped like a bunch of grapes, the northern stem part of Delaware, the center comprising nine counties of Maryland, the tapering tip in Virginia. It has borne its name for three centuries, ever since the first settlers on the western side of the bay began referring to the land opposite as the Eastern Shore.

While we tacked and tacked again, the afternoon air became a silver haze, smoky from burning leaves. A slight film of cloud slid across the sky, so it, too, was silvery. Yet somehow colors were intensified: the massed trees turning russet and copper, cornstalks drying in the fields, the contrast of white barns and silos against evergreens.

Birds were everywhere, reminiscent of an earlier America. There were Canada geese in the hundreds. They flew overhead in long trailing echelons, receding in perspective until the most distant were faint plumes on the horizon; they lifted from fields in waves; they floated in rafts on the water, watched over by wise old ganders, heads high and swiveling. Among the black and gray of the geese was the pure white of wild swans, rare elsewhere, plentiful on the Chester. And shuttling through and over these great birds were flights of lesser ones—ducks, coots, even gulls and fish hawks, eying patches of roiled water.

We had drifted by Grays Inn Creek, where Eugene du Pont has a shooting lodge, and on into the Corsica River, past the home built by John J. Raskob, financier and political leader of another generation. In the faint chill breeze Finisterre ghosted through gently rolling countryside in which sleek cattle browsed behind rail fences finally to anchor where the river narrowed to a creek, the creek to a pond. After the sails came down with a rattle of slides there was only the sound of birds, wing beats and voices by the thousand, like the hum of a bumblebee's nest. The sun was low, and already the breeze had stilled, trees reflected, inverted, under the shore. Bill and I walked the deck, wordlessly, hands in pockets, and leaned against the rigging to watch.

Fall and spring—these are the magic times to cruise Chesapeake Bay. I have been under sail from the first warm days of late March to Christmas. When the New England coast, the Great Lakes, the Pacific Northwest and even Long Island Sound are too frigid for pleasant cruising the Chesapeake enjoys an additional month to six weeks on each side of summer. A boat brought down for winter lay-up, or en route to Florida, can cash in on both. During these interim periods days are likely to be warm and the nights cool, breezes are fresh and reasonably constant. There are few squalls. The water is clear and bracing for swimming. Air and waterborne pests—insects and jellyfish—are rare.

Summer has a different quality. Then, in the heat, there is a sense of almost voluptuous indolence, tempered always by the threat of squalls gathering over the western land. Crews laze under awnings, and screens are fitted at sundown. The water lies opaque and tepid. Fishermen sit in rowboats, long cane poles extending like the antennae of insects; their cork bobbers float immobile. The tempo of life slows. Some like it better.

Next morning it was still sunny, although a high haze softened shadows. Treetops waved, and a faint growl came from the upper rigging. The pen of the barograph traced a steady decline. We took our time over breakfast, for it was not the day for an open-water passage. Finally hoisting sails, we drifted from our anchorage, feeling the breeze increase as the river widened, to find a wet beam reach across the bay to the shelter of the Magothy River. Anchoring in the lee behind Mountain Point, we had lunch, then reset sails for a brief afternoon of exploration of the headwaters. Gradually during the day the clouds thickened and lowered, and well before sunset we swung on a mooring off the clubhouse of the Gibson Island Yacht Squadron.

Now I had my harbors-can-be-so-nice feeling, one of the best parts of cruising. There was a chill edge to the wind on deck, but when I went below I felt the snug coziness that exists only in the cabins of small boats. A coal fire burned in the bulkhead stove, a kettle simmered, oil lamp and candles shed a soft glow over books and polished mahogany. We settled on the cushions to listen to the hi-fi system, beginning with Heifetz playing Bach's concerto in E major for the violin, "the one with the bounce," as Bill put it. Sometime before dawn I was awakened by the patter of rain on deck. Finisterre shook to strong gusts of wind. Pulling the blanket tighter around my neck, I reflected again on the joys of cruising, especially the Chesapeake. Tonight others could struggle with flogging sails somewhere offshore: for us the squall was a lullaby.

We came on deck to find sky and earth scrubbed clean by the broom of a fresh nor'wester, clear cold air flooding down from Canada. Finisterre responded to the call of the wind, and soon we were past Mountain Point and into the bay.

It was a fall and spring day, both together: fall in the heft of the breeze, spring in the warmth of the sun. Wing and wing we skirted the beach to Sandy Point, speed diminishing as the Magothy dropped astern. As often happens, the wind had funneled down the river—a local phenomenon sought in light weather, especially by racing skippers, but to be remembered with caution in heavy weather or when squall clouds gather.

A midsummer bay squall is not to be underrated. Three centuries ago John Smith wrote of the first one encountered by a European sailor: "The winde and waters so much increased with thunder, lightning and raine, that our mast and sayle blew overbord and such mighty waves overwracked us in that small barge it was with great labour we kept her from sinking by freeing out the water."

As we moved south the Severn opened to starboard, Kent Island slid by to port, Bloody Point lighthouse ahead acting as a navigation aid and reminder of the past. On Kent was the first settlement of the Upper Bay, a trading post established by William Claiborne in 1631. In that early time the waters were as clear as the open ocean; fish swarmed the rivers, and every shoal was carpeted by oysters. Trees stretched away in all directions, the forest primeval, individual trunks large enough to be hollowed into canoes capable of carrying 40 Indians. Under the lofty canopy was little underbrush. Deer roamed in a cathedral peace of dim light and quiet.

Among local cruisers today there is an endless argument about the "best" of the rivers. Flowing into the bay are some 40 major estuaries, each fed by its own complex of branches, all feeling the pulse of the ocean to the remotest headwaters, for the entire Chesapeake is tidal. Devotees of the upper and lower areas endlessly sing the delights of their own wide and lazy streams. Hidden harbors are played like cards, and always a secret gunk hole is the final trump, perhaps only to be described, exact location and pilotage details too precious to be divulged, even to make a point.

Before us were my own twin favorites of the Chesapeake. Behind Kent Island stretched Eastern Bay, open mouth of the Wye, the Miles and lesser streams; while a little farther along, past Tilghman Island, lay the Choptank River and its myriad feeders, wandering far across a peaceful countryside. Only from the air could the pattern be wholly comprehended, bringing visual reality to statistics of the U.S. Coast and Geodetic Survey, which show that the "tidal shoreline, detailed, of Chesapeake Bay and all its tributaries totals about 5,600 statute miles," against "4,840 statute miles of general coastline from the state of Maine to the state of Washington." In other words, measurement of each squiggle of each Chesapeake creek to the head of tidewater, or point where the water narrows to a width of 100 feet, exceeds the coastal outline of the continental United States. Nowhere is there a straight line, everywhere there is one more creek and cove. And in the whole bay country the configuration was never more pronounced and thereby delightful for cruising than the waters over the bow of Finisterre that fall morning.

Again it was the wind that decided our destination. It was too good a day not to sail as far as possible. Wordlessly, when Bloody Point lighthouse came abeam, course was altered for Poplar Island Narrows. Past Jefferson Island we sailed, looking somewhat wistfully at its lovely harbor, and ignored the short cut of Knapps Narrows, a canal used by oystermen and crabbers to save distance. Avoiding the ever-present fish traps, we jibed off Blackwalnut Point to enter the Choptank River by a well-charted channel. Not very far inside, the river is more than five miles wide, making it a rather respectable bay in itself. Laying a course for Choptank light, I switched on the automatic pilot and relaxed against the mizzenmast, nothing to hit that couldn't be seen, nothing in sight, nothing to do but lazily consider the next choice. For at the lighthouse, now becoming visible ahead, we could swing to starboard, following the Choptank past the small city of Cambridge as far as we cared to go, almost 50 miles from Black-walnut Point into the heart of the Eastern Shore. Or at the light we could sharpen up to port and run the Tred Avon River beyond the village of Oxford, selecting an anchorage from an array of the loveliest creeks—by almost universal agreement—of the entire Chesapeake.

We compromised, followed the Chop-tank for a look into La Trappe Creek, then retracing our course into the harbor of Oxford. Here, in a snug inner cove, were tangible reminders of the golden age of sail. Maryland many years ago passed a law that oysters could not be dredged by powered vessels, so bugeyes and skipjacks, with their picturesque clipper bows and raked masts, still ply their ancient trade each winter, drowsing during the spring and summer tucked away in such byways as this, refitting each fall. Nor were these the only links with history. The village, with its spreading trees and smooth lawns, white picket fences and green shutters, bears a close resemblance to a New England town. The surrounding countryside retains much of the graciousness of an earlier era, fields running down to the water, colonial houses set back in flowering groves. And the flourishing boatyards rimming the harbor prove that it is continuingly oriented to the water.

As is our wont when cruising, Finisterre poked in for supplies and a look, and poked out again in quest of a deserted anchorage. Passing Plaindealing Creek, which took its name from the Quakers who traded fairly with the Indians, we continued up the Tred Avon to Trippe Creek, while the sun dropped toward the horizon. Beyond Deepwater Point lay a sheltered bowl of a harbor; almost regretfully we dropped the anchor, hating to end so perfect a day.

If you live right, sometimes—sometimes—the gentle gods who watch over the affairs of Chesapeake creeks are kind. We awakened to a moderate easterly breeze, carrying with it the freshness of the ocean lying just beyond our rampart of land. It still felt like summer. Gingerly I put a foot over the side to be rebuffed by the first chill of winter. But never mind. Always, cruising, there are the compensations. The electric anchor winch whirred, saving more energy, and one heave on the sheet unfurled the roller jib. Finisterre heeled ever so slightly, and we began retracing our course to Eastern Bay, heading now for the Miles River and the town of St. Michaels.

Within the span of my acquaintance, St. Michaels has changed, but only to accommodate the expanding fleet of pleasure boats. At the end of World War II it was a drowsing harbor frequented principally by fishermen, crabbers and oystermen; now marinas have blossomed, slips aplenty for wandering yachtsmen. At the head of the docks is a supply store, while nearby is a crab factory.

Here, as in most other towns, is found one of the principal joys of Chesapeake cruising: living off the land, or perhaps I should say water. Depending on the season, there are soft-shell crabs or steamers to buy, big bay busters transmuted from blue to bright red by steam and spices—or ready-picked back-fin meat, succulent lumps as big as your thumb. There are fresh shad and roe in the spring and native rockfish in the fall. After the leaves begin to drop, oysters may be purchased ready-shucked or by the barrel, the barrel to be lashed on the stern and the oysters opened as you sit along the rail, tossing shells into the water alongside. Local sea food can usually be bought, for fishing is still a major source of income to the area, but there is always the do-it-yourself system. Few are the creeks which will not yield pan fish and crabs. In fact, a long-handled crab net is a standard Chesapeake cruising appendage.

It was nearly dark when we returned to Finisterre after a shopping expedition. Almost anywhere else it would be necessary to spend the night alongside a dock, whether we wanted to or not. But starting the engine, we powered confidently forth as I scanned the chart for a harbor. Almost immediately I discovered Leeds Creek, less than a mile away. I had never heard of it before that moment, but as the red ball of the sun vanished without glare over the church spire of St. Michaels, Finisterre crept into the embrace of the first cove to appear to port, electronic depth finder never showing less than the charted eight feet. It was a harbor that would be famous elsewhere. After the anchor splashed down we lingered on deck, savoring perfection. Around us fish broke. Gulls almost too fat to fly fluttered away. Crickets and frogs began their evening chorus and, with the fading of the last light, Venus shone like a suspended jewel, no more distant than the nearest treetop. By my side Bill said softly: "Think how few people today can know such moments. Most places there is noise and hurry. Here there are only stars—us and them."

In the morning I thought out the day—back to the Miles, then into the Wye East branch for the whole length of Wye Island, poking into creeks, glimpsing the magnificent colonial splendor of Wye Plantation; in all, one of the most beautiful islands in the world, in its own way worthy of comparison with any in the Aegean, the Baltic, the Caribbean, the Pacific. So now it comes out, my favorite part of the Chesapeake—a rambling few miles of peace and solitude and quiet green lanes to seep into the soul after the boisterous blue wastes of ocean Finisterre and I have known together

It was a day when time was suspended. morning passing quietly into noon, when the water didn't seem too cold for swimming after all, afternoon sliding toward dusk and soft night. Faint airs carrying the essence of tilled countryside moved us for a few hours. When the breeze faded with the light we dropped anchor where we happened to be, for the whole estuary was a harbor, snug and safe.

There was no anticlimax when the morrow brought back the fair-weather cycle of southerlies. Finisterre recrossed the bay to a narrow entrance off the South River, barely two beams wide. Inside, Harness Creek opened, a haven no gale could even ruffle, a sanctuary to remember some screaming night off shore. Yet at its head was still another harbor, almost hidden. Finisterre finally dropped anchor in a veritable teacup, a true gunk hole, surrounded by land practically within stepping distance. Within two airline miles lay Annapolis—a lovely colonial city that had gracefully made the transition to the modern age, a seat of government, learning and culture, yet part of the stream of life: automobiles bumper to bumper, neon signs, the electronic voices of the hucksters. But here in Harness Creek nothing stirred or spoke, not even the trees holding us in close embrace.










Love Pt.



Sandy Pt.



Bloody Pt.






St. Michaels







To rent a boat for a cruising vacation on the Upper Bay, write or phone one of these brokers:

ANNAPOLIS YACHT SALES INC., 100 Compromise St., Annapolis. Phone Colonial 3-3321

HENRY T. MENEELY, 319 Sixth St., Annapolis. Phone COlonial 8-8741

ARNOLD C. GAY YACHT YARD, I Shipwright St., Annapolis. Phone COlonial 3-9277

GEORGE B. WALTON INC., 4th & Severn Ave., Annapolis. Phone COlonial 8-5191

ANNAPOLIS BOAT RENTALS INC., 419 Chester Ave., Annapolis. Phone COlonial 7-7205

CRUISING INC., Galesville. Phone University 7-2018

THEODORE GRAVES, Dickerson Boat Yard, Cambridge. Phone Academy 8-2914

S. WICKES WESTCOTT, Kennedyville. Phone Fieldstone 8-3134