Chesapeake to Maine

Spring 2023

By Paul Brown

As a country kid more familiar with Jersey cows than boats, I became interested in wind propulsion during the 1973 gas crunch. A sailing vessel seemed like a romantic and cheap way to get away from it all.

A friend, we’ll call him Preston (not his real name), is a grand nephew of the founder of an internationally known company. He was what you would call a rich kid. He had taken a year off with his wife and three kids and sailed the Caribbean, had come back to New Hampshire to put the kids in school and actually work.

A few years older than Preston (quite a few), I had confided to him that I, too, would like to sail someday.  I don’t know if it was the challenge, the freedom, or my Yankee stinginess in getting propulsion power from the wind, but it was something I wanted to do for myself.

Preston encouraged me.  He bought me a gift subscription to “Cruising World” to keep the dream alive.

After several years of poverty, my business improved with the economy, and I was offered a Thunderbird 26, in good condition, on a trailer for $7,000. I thought about it and decided I didn’t want to sail. Re-thought it and said, “Time to step out of the rut. Do it.” I did.

Sitting in my yard on the trailer, the rudder needed a fiberglass repair. Preston showed up one morning with the materials and repaired it. I might have procrastinated through the sailing season.

We towed the ‘Bird up the Maine turnpike with a borrowed truck. While I didn’t know the difference between standing and running rigging, Preston supervised the stepping of the mast, attached the boom and bent on the sails. He advised me about mixing oil with the gasoline for the outboard motor, something I hadn’t considered. Finally, with the boat tide-floated off the trailer and tied at the dock, he produced a bottle of champagne for a christening.

I found, through that summer and several after, that Preston was very good at catching fish and at foraging. And whatever he caught or foraged, he could prepare in various mouthwatering ways. While I probably could have been happy with the Thunderbird for the rest of my sailing days, I felt that I needed something larger for more comfort and safety and with the greater ability to make longer voyages.

Answering an ad for a pilothouse sloop in Maryland, Preston agreed to examine it with me. It was an interesting boat, but we decided we’d stop at some yacht brokerages and make some comparisons. While driving through Annapolis, we stopped at one of his haunts for lunch. Sitting at the bar, he ordered a “shooter” for each of us. Now, I am as naive as Preston is sophisticated. I am as country as he is cosmopolitan. When Preston ordered the two shooters, the bartender repeated, “Two boogers and blood coming up.”

Quickly, two double shot glasses were in front of us, each containing some sort of an organism in a bloody red fluid. Preston instantly upturned his glass and gulped the contents. And he turned to me, waiting. I looked at the substance in front of me and turned my eyes toward a couple sitting at the end of the bar a few feet away. They were watching, waiting. Expectantly. What am I to do? I rolled my eyes heavenward, raised the glass to my lips, upended it and swallowed the contents. I was relieved that it all went down and stayed down. Then he ordered two more.

We went on to the yacht brokerages, and at one of these, I found my boat and made a deal, pending the results of a survey. The boat was a Beneteau Evasion 32, a pilothouse ketch. I liked it for its full keel and diesel engine controls, both in the pilothouse and cockpit. And a reasonable price.

A few weeks later, the survey and sea trial were made. The deal was finalized, and we prepared to bring the boat from Maryland to New Hampshire. After attempting to entice two experienced sailors as crew, we settled on Preston’s one employee, a young man barely out of his teens, and my older brother, Rick. Rick was not “experienced” but had crewed on the Satori of “Perfect Storm” fame. He had assisted in hauling the vessel off a New Jersey beach and crewed from there to Norfolk about nine months earlier.

Our route was up the Chesapeake, through the Chesapeake Delaware Canal, down the Delaware River, around Cape May and across to Block Island for the first hop. We refueled at the entrance to the canal. At sunset, we exited the canal and turned south to go down the river.

As soon as we made the turn, Preston, who had been drinking beer steadily all day, announced that he was going below to get some sleep.

“But Preston…”  I began.

“Look, just follow the lights. See that range down there, see that one back there.  Keep them lined up.  And watch out for the barges.”

“But Preston…” I whined, “Why not pull over to the edge of the channel and drop the hook until daylight?”

“Nope got to get back to work on Tuesday. Don’t have time. Don’t worry. See you later.”

He disappeared below, leaving the radio on the table with his ever-present Jimmy Buffett tapes, howling away.

The kid followed suit. “Wake me up if you need me.”

“Fat chance,” I thought.

Rick and I were left alone, motoring down an unfamiliar river in the dark.  I had not partaken of any alcohol but had had a ham sandwich at lunch. That and the Scopolamine patch behind my ear combined to make my mouth as dry as a potato chip. Jimmy Buffett continued to howl. I switched the player off, and the decibel level was lowered considerably, only the sounds of the Perkins pushing us along and the river rushing past the hull. I concentrated on the navigation lights that marked the river channel.

I’m not certain when we saw the first tug and barge, but we saw many that night, and these were by far the most frightening experiences of the trip.

Far ahead, we would see a light, and then perhaps a cluster of lights, heralding the approach of some sort of shipping.  Within a few minutes, the cluster would begin to take the shape of a tug, moving upriver, followed by an enormous barge that would virtually block out the stars.

I could picture myself either too far out into the channel to be run down by one of these towering behemoths or, in avoiding some, to stray out of the channel and running aground.

It was a long night. Each channel light was numbered, and I carefully checked each off the chart.  Rick and I took turns at the helm and making coffee. The first grayish hint of dawn found us within a few miles of Cape May, where we had planned to shortcut the cape by taking the Cape May Canal. However, as daylight began to illuminate our world, we could see that the shore was becoming indistinct.

Fog. I hate fog. But I had been carefully punching waypoints into the LORAN; and since entering the canal appeared risky, I had plotted a course around Cape May. The kid had awakened and appeared, rubbing his eyes. He was quite enthusiastic at the beauty of the morning and the barely visible shore. I set him in the helmsman’s seat, steering to the compass, which he did quite handily. Soon, we were in thick fog.

Far enough below Cape May to clear some hazards, we turned east, out into the Atlantic, and then turned north. I had set the northerly course when Preston called from below, “Where’s coffee?”

I replied that the waitress would bring it in a minute, along with the bacon and eggs. And be sure to give her a big tip. But I was relieved that he was awake and apparently rested. In a few minutes, coffee mug in hand, he inquired as to our whereabouts. I showed him our position on the chart and our heading.

I said, “See ya later.”

I flopped onto the center cabin berth and closed my eyes, heaving a big sigh.

About four hours later, probably just before noon, I awoke. I peered out from the center cabin, through the pilothouse into the cockpit. Preston was at the tiller, steering with his foot, wearing nothing but shorts in the bright sunshine. A mile or so off to our port were the beaches and the condos of New Jersey. Preston was swigging a beer and regaling his audience, Rick and the Kid, with some story. Jimmy Buffett was howling from the tape player.

Our plan had been to cross from Cape May to Block Island. With the fog, we had decided to stay inshore, out of the shipping lanes to and from New York City. With clear weather now, we decided it was safe to go offshore.

Preston had brought the autopilot from his boat as a loan, and he busied himself at installing it. He had mounted the wheel hub, the controller and the motor and was installing the belt connecting the motor to the wheel. The belt suddenly snapped, resulting in an immediate stream of invective from his lips. I was not particularly perturbed, as I had accepted the likelihood of steering the whole distance, anyway.

But Preston was not to be daunted. He tried various means of repairing the belt and eventually called for a test. He had used electrical tape to fasten the belt to a piece of rope of about the same length. After a few adjustments, we all sat back to watch “Otto” take over the steering, maintaining the proper heading much more steadily than a human helmsman.

We had been motor-sailing much of the distance thus far. Occasionally, when conditions were right, we shut down the engine and enjoyed the quiet of the sail. Our deciding factor as to sail or motor was to maintain at least five knots.

Throughout the planning stage and the actual voyage, we were concerned about the shipping out of New York, particularly at night. And as we entered that night, we set up our watch schedule.  Preston had carefully drilled the kid on the pattern of lighting to be seen on ships. I double-checked my “Chapman’s” and tried to memorize the patterns.

When my watch came in the wee hours, I had a strange feeling of comfort and security. The engine purred reassuringly, never changing pitch, hour after hour. “Otto” whirred away at his task, holding a perfect course toward Block Island and New England. Now and then, I would see a light in the distance, but nothing that appeared to be a menace. It was far different from the previous night.

At one point, the wind piped up and was coming almost dead ahead so that the sails were luffing, the boom dancing.  I considered changing course slightly, but Preston suddenly appeared, hearing the sounds.

I was not inclined to go above decks to lower the sails, but Preston had no such compunctions. Donning a safety harness, he clipped to a stay and headed forward. I held a torch to light his way, and soon the sails were dropped and furled.

The night passed without incident. Dawn brought with it another beautiful day and a gently rolling sea. We ate, drank, slept and did what any four guys would do on a sailboat, attempting to maintain a schedule, expecting to close on Block Island before dark.

At dusk, we could see Long Island in the distance and the light at Montauk Point. It was at this point that the LORAN chose to crash. The readings were inconsistent. I was somewhat concerned, approaching shore, in the dark, without knowing exactly where I was. So much for trusting in electronics.

Preston, on the other hand, was unconcerned.  I showed him where I thought we were on the chart, but he disagreed, using the light at Montauk Point as a mark.

We argued about it for a while, but I rarely challenged him.  Soon, he discerned a red light in the direction of Block Island. He commented on it and watched it carefully for several minutes.

Preston was looking for a flashing red light at the entrance to Great Salt Pond on Block Island. The red light we were steering toward was not flashing. He looked at it again with binoculars.

“Better slow down,” he cautioned, “That might be a boat.”

I cut back on the throttle, and we all stared at the red light. Was it a boat? What was it? Where were we? I was busily hopping back and forth from the chart to the LORAN, hoping it would come to its senses and tell me where we were.

The entrance to Great Salt Pond is 75 degrees magnetic from the Montauk Point light. When we reached a point with a bearing of 255 degrees to the Montauk light, we turned to 75 degrees, and the light was dead ahead. We finally decided that the red light must be the marker to the entrance to Great Salt Pond, which, ultimately, it turned out to be.

Later, talking to another sailor at Newport, Preston commented that the flashing red light was not flashing. The response was, “No, it’s a ‘fixed red.’”

Preston looked at the chart; “Hmmm, ‘F R’ doesn’t mean ‘Flashing Red,’ it means ‘Fixed Red.’”

He avoided eye contact with me for a while after that.

We approached the entrance to Great Salt Pond at around midnight. It appeared to be a narrow entrance but was well-marked. With the help of a powerful spotlight, we picked our way from marker to marker until the channel opened up to the Pond. Within a few minutes, we had dropped anchor, secured it in the mud of a New England state, and heaved a collective sigh. We had made it.

The next day, on the way to Newport, the weather clouded over, and the wind piped up to 15 to 20 knots. We then found that the boat sailed nicely. We were warm and comfortable in the pilothouse. At Newport, we left the boat for a week and then returned. The first night found us waiting for the tide to turn at the entrance to the Cape Cod Canal, being warned by the bridge tender about a southbound tug, finding that the tide hadn’t turned and making about two knots at full throttle.

We exited the canal and crossed Massachusetts Bay in the dark, finally arriving at Little Harbor in New Castle, New Hampshire, late in the afternoon. Thus began a decade-and-a-half of sailing this comfortable ketch that was easy to single-hand. We did three Fundy Flotillas and made many friends along the way. This country kid would never reach the level of sailing savvy of most of the people I’ve met, but from my first season on the Thunderbird, it was the most joyful time of my life.

Paul Brown is a “farm kid” who never expected to be a “yachtsman.” He sailed out of Dolphin Marina in South Harpswell, Maine. Previous voyages include Brownscow from the Chesapeake Bay to eastern Nova Scotia and crewing everywhere from the Florida Keys to the Dry Tortugas. He lives in the house where he was raised, on a dirt road, in Raymond, N.H.