Building Boats and a Key Legacy on the Waterfront

“We won’t be able to pay you much,” Nat Benjamin explained frankly. 

“Actually, we won’t be able to pay you anything,” Ross Gannon interjected, “We can’t really afford employees.”

The three of us were standing around a massive antique table saw that served as the business office of Gannon & Benjamin Marine Railway. It was a cool September morning in 1981. I was 21 years old, adrift, broke, with no job and not much direction. I grew up on the Vineyard sailing on my family’s wooden schooner and I had been around boats almost my whole life, but I had no clue how to make a career of that. I hadn’t followed my friends from MVRHS off-Island to go to college, and I was just trying to find my way.

Nat Benjamin and Ross Gannon had recently opened a small boat shop and marine railway on a stretch of beach at the mouth of Vineyard Haven Harbor. They were, by their own admission, not sure how or even whether it could succeed. They had a vision of a business that would focus exclusively on the repair and construction of wooden boats using traditional materials and methods.

They were true “if we build it, they will come” dreamers.

After seeing the disappointment in my face, Ross added, “What we can do is teach you everything we know and give you a chance.”  

Little did I know how critical and life changing it was for me to shake their hands and ask, “When do you want me to start?”

Nat replied, with a grin, “What’s wrong with right now?”

That began an education that I could never have imagined and still cannot. When Ross told me that he and Nat would teach me everything they knew, I don’t think he fully understood all that would entail. What transpired over the next five years for me was the beginning of a career in boatbuilding and yacht service that has spanned over 45 years.

The background and history of Gannon & Benjamin have been well-documented in recent years through best-selling books, numerous articles, documentaries and movies. While there is an impressive list of hundreds of some of the most beautiful and historic classic wooden yachts that have ever been constructed or restored at G&B, their greatest accomplishment and the most important contribution they have made to the traditional yachting world may be the number of craftsmen and disciples that have learned under their tutelage. They have truly become masters of their trade and feel an obligation to pass on the tradition of wooden boat building. As one of the first two full-time employees/apprentices, I can attest to the deep-rooted appreciation of well designed and constructed vessels that Nat and Ross imparted on me and countless others.

As I reminisce about those years, so many memories come flooding back to me. Those experiences were in many ways the foundation of my career and my adult life. The lessons I learned went far beyond just boatbuilding. I learned the value of pride in craftsmanship and the appreciation of superior materials. I began to understand the importance of good sharp tools. Above all, I developed a relentless work ethic that I witnessed from Nat and Ross every day. That is a fundamental work philosophy that I have carried with me throughout my career.

 

My first assignment during the fall of 1981 was to begin the demolition process of the decks, cockpit, interior and transom of a 40-foot 1906 Lawley designed and built gaff rigged sloop.

Venture was a fixture on the Vineyard Haven waterfront. I had grown up racing against her on the weekends and had always marveled at her sleek graceful lines as well as her quick turn of speed. She had been given to Nat by Pat West, one of the elder statesmen of the Vineyard Haven traditional sailing community with the hopes that she could be given a new life after decades of hard use.  

Nat provided me with brief instructions and pointed me towards the tools that I would need to cut and split and hack apart the old, tired, sometimes rotten pieces and parts of this once proud and elegant classic. Almost immediately, after climbing on board and starting to work, I began to experience the unusual sensation that I was in a different time and place. I could almost feel the presence of the master boatbuilders that had built Venture 75 years earlier. It was as if they were looking over my shoulder. I struggled to remove deck beams in spite of the decaying wood. I marveled at the perfect half dovetail joints where each beam notched onto the sheer clamp. I could still see the plane and chisel marks on the old rotten transom knee. I started to appreciate the craftsmanship and skill that it took to build a sailboat that until then I had only watched sail by. 

As I cleaned up at the end of the day and assessed my progress, I felt a sense of pride and satisfaction that I was not familiar with. I was hooked. After seeing that I was eager and willing and that I had enough basic skills to not injure myself, Nat and Ross began including me in other projects that were in the yard. I gradually gained their trust and respect and before long I truly felt part of the Gannon & Benjamin team (small as it was).

 

In the very early days of the yard, we (a team of four) constructed the 150-foot wooden dock that has become a fixture of the Vineyard Haven waterfront and has withstood numerous hurricanes and northeasters. We built the dock without the use of a barge or crane or pile driver. We used old telephone poles acquired from the phone company as pilings, which were deposited into the lagoon, a few miles from the yard. We towed them two or three at a time out of the lagoon to the beach in front of the yard using an ancient and leaky double ended workboat powered by a temperamental Buda diesel engine that was prone to stalling at the most in-opportune times.

I marveled at Ross’s ingenuity and skill in constructing a movable, three-legged timber A-frame that we used to hoist the pilings vertical and position them. We used an old gasoline-powered pump connected to a steel pipe that we maneuvered alongside the pilings in order to “jet” the pilings down into the sand. Two of us would twist the pilings back and forth using logging peeves while the other two would direct the pipe. This was an arduous process, and I can still recall the ache in my shoulders as the sun was going down the day we set the last piling.  

Upon reflection, I can’t even imagine who would undertake such a challenge but at the time I never doubted Ross and Nat. They acted as though it was just another day’s work. To them, nothing was impossible.

The first boat that was built in the waterfront shop in 1981 was a 20-foot catboat named Meta B that Nat designed for a customer in Harthaven on the Island. I assisted Nat in lofting the full-size lines on the shop floor where I first learned the concept of a “fair curve.” I watched in wonder as Nat lay down on the floor to sight the line of a wooden batten held in place by small nails on either side. He would pull a nail here and bend another there until he saw the perfect line. I came to understand that this process was the true essence of a well-built boat.

 

In my career, I have been fortunate to have worked with many wonderfully talented yacht designers, naval architects and master boat builders. I can say without hesitation that I have never known a soul who could see and draw a fair line like Nat Benjamin. I believe that it is a god given ability akin to a musician with perfect pitch.

As Meta B started to take shape, I became more confident in my abilities, and was given more responsibility in the shop. One morning after the hull was completely planked, I was going about my assignment of gluing and tapping with a small wooden mallet the hundreds of Cedar plugs (bungs) that covered the countersunk plank fasteners. Ross tapped me on the shoulder and said “grab your tape measure and meet me in the hull.”

I scrambled over the side and followed him to the bow.

“We need to build two sets of heavy sawn frames in way of the mast partners in order to strengthen that part of the hull,” Ross explained. “Grab some pattern stock and make a template that fits the inside of the hull. Then record the planking angles with a bevel gauge at the different points in the hull because the angle changes the whole length of the frame.”

I looked at him with what must have been a blank stare for a few seconds. He grinned at me through his full beard and winked.

“You can do this,” he said. “Use a piece of the two-inch white oak that’s out in the woodshed.” Then he walked away.

I sat in the bow of the boat for a few minutes and tried to remember all that Ross had explained. I took a deep breath and climbed out of the boat to get my tools and some wood. I’m sure it took me twice as long as it should have to build that port side frame but after cutting and shaping the heavy piece of oak, I slid it into place, and it fit against the planking like a glove.

I could hardly contain my excitement when I asked Ross to take a look at my handywork. 

“Looks good,” he said. “Now you better get started on the starboard side.”

I rushed to the wood pile to find the next piece of oak and built the starboard frame in half the time. I was feeling just a little smug as I climbed into the boat to slide the frame into place. As I crouched into the bow, my heart sank. I realized that I had forgotten to mirror the bevels and that I had made another port side frame. I was panic stricken when I sheepishly approached Ross and explained what had happened.

“Well, what are you waiting for?” he barked. “Find another piece of oak and do it again. And throw that other frame in the wood stove. You don’t want to be looking at that.”

Needless to say, I made that starboard frame and then the second set of frames and went on to contribute to the completion of the boat. The lessons from that experience were many but the way Ross showed me that he believed in me gave me the confidence to keep learning. 

 

In late February of 1984, the Vineyard was hit with a classic winter northeaster. Vineyard Haven has long been the home of a wonderful fleet of classic wooden sailboats. Many of these boats spend the winters on their moorings behind the robust stone breakwater.  

The forecast was for two days of gale force winds, snow and freezing rain. After the second day, the forecast changed to warn that the storm was going to extend to a third day and that the wind was expected to increase for a period of 12 to 18 hours.

The shop was closed for the weekend, and I received a call from Nat at home.

“Jeff, can you meet me down at the shop right away? We have to try and get out to MYA. The owner is off-Island, and no one has checked the mooring pennant and chafe gear.”   

MYA was a beautiful 50-foot Concordia built schooner. She was owned by Matthew Stackpole, one of the yards great friends and supporters. I didn’t hesitate, and hustled to the waterfront where Nat was pulling into the shop in his old pick-up truck. We walked down to the dock and tried to look out to the mooring field. The wind was howling and freezing rain was pelting us in the face.

After numerous futile attempts at launching the work skiff through the breaking surf on the beach, we slid a little Catspaw dinghy that we had just built a few weeks earlier into the back of Nat’s truck and drove it around to the beach at Owen Park on the other side of the harbor where we were somewhat protected by the breakwater. We launched the dinghy and Nat sat on the thwart pulling on the oars and I knelt on the floorboards in front of him with my hands over his pushing the oars while he pulled. 

It took us almost an hour rowing as hard as we could to make it to the stern of MYA. She was heaving up and down and yawing back and forth as the 40- to 50-knot gusts hit like a freight train. We made our way to the bow and found the heavy mooring pennant had chafed through two of the three strands. It seemed like it could give way at any moment. We hurried to the cockpit and found as much heavy line as we could and climbed again into the little dinghy. We worked our way up wind to the mooring ball and made fast three extra pennants and threw the lines up onto the deck. We climbed back aboard and secured the makeshift pennants to the bits and bow cleats and wrapped them with as much chafe gear as we could find on board. 

We stood dazed on the bow, exhausted and freezing cold to our bones. We looked again at the chafed pennant that had all but disintegrated, looked at each other and hugged. It was a moment I will never forget. Nat taught me that day that a boat is more than pieces of wood screwed together but rather an organic object that has a soul. 

 

These are just a few of the numerous experiences that have shaped my philosophy about boats and boat building and about life. I hope that they also give a small glimpse into the legacy of Nat Benjamin and Ross Gannon.

Life circumstances took me away from Martha’s Vineyard. I went on to work at other shipyards and then to start my own boatyard and boatbuilding business. I chose to adopt the more modern “cold molded” building technique for some of the boats I built but in 2003 I was commissioned to build Catriona, an L.F. Herreshoff designed  58-foot Bounty Ketch in the traditional “plank on frame” technique.

This project coincided with the building of the 65-foot schooner Juno at Gannon & Benjamin. I was thrilled to realize that I was going to be purchasing the lumber and timbers from the same source that Nat and Ross were. I felt like I had made my way.

In my diverse career I have had the pleasure of working for and with some of the most respected companies in the yachting industry: Dions Yacht Yard, Sparkman & Stephens, Derecktor Shipyard & Rybovich Shipyard. 

I have worked with almost all of the boatbuilding materials: wood, aluminum, steel, fiberglass, carbon fiber. I have built or refit vessels from a 12-foot dinghy to a 320-foot mega yacht. I feel fortunate to have had a successful career doing something that I love.

But in retrospect, I feel that my most important accomplishment and what I am most proud of is that I have stayed true to the values and fundamental principles that Nat and Ross instilled in me 45 years ago. I truly have lived an apprentice’s life.

Jeff Grey, aboard S/V GIOIA III, Palm Coast, Fla.

This article appears in May 22, 2026.