The Great Schooner Race

Publish date:
Heritage takes a victory lap after winning the Cutty Sark Award Trophy

Heritage takes a victory lap after winning the Cutty Sark Award Trophy

I arrived in Rockland, Maine, on an early afternoon in July with a backpack, my camera and little else. Though traveling to an unfamiliar place to race with a crew of strangers has been a common theme in my sailing career, I had no idea what to expect from the massive wood and steel windjammers taking part in the 42nd Annual Great Schooner Race. Fiberglass is more my scene.

Fortunately, I wasn’t left to figure it out on my own. Marti Mayne, the affable and deeply knowledgeable events manager for the Maine Windjammer Association greeted me as soon as I’d stepped out of my car and led me down to a lobster boat captained by Mike McHenry. McHenry also happens to be the former owner of the windjammer Angelique—the boat that was my destination that evening. Between the two of them, I had more information than I could absorb about the steel-hulled ketch and the Great Schooner Race in which she would be competing the following day.

Despite the bad weather, the boat’s crew and passengers ready the boat to sail 

Despite the bad weather, the boat’s crew and passengers ready the boat to sail 

The whole way to Islesborough, I kept an eye on the horizon and was occasionally rewarded with a glimpse of sails between islands or through the light fog. When we arrived, several boats were already in the process of anchoring and several more were approaching. We circled them, getting a close look at the meticulously maintained hulls and acres of sails collapsing downward to be flaked for the night. Marti promised me I’d recognize Angelique the instant I saw her by her tanbark sails. Sure enough, a spread of dark red canvas soon appeared through the mist and anchored along with the rest of the fleet. Angelique’s gaff ketch rig, glossy green hull and distinctive sails were breathtaking.

I was welcomed aboard by Captain Dennis Gallant, an amiable gentleman with a seemingly infinite number of stories and fun facts from his years with the fleet. He, in turn, introduced me to my bunkmate, Meg, who showed me to our cabin. By the time the tour was over, it was dinnertime. One of the women on the boat would later tell me that time didn’t exist on Angelique. “The only measure of time we’re interested in is when they’re going to call for a meal,” She laughed, and it’s true. Angelique has excellent cooks and among the passangers, the food rivals the sailing and the locales in popularity. Every meal was even served with a vegetarian and gluten-free option per the specific needs of the guests on board.

Over dinner, I met the other passengers. They were largely of retirement age but ranged in sailing experience from having owned their own boats to being absolute beginners. They came from as close as neighboring towns in Maine to as far away as Maryland. Some came with their spouses, some with grandchildren, others came alone. To my surprise, one common thread in their stories was that they were almost all repeat visitors—a testament to the experience that is tall-ship sailing.

The dingies gather round for their own race

The dingies gather round for their own race

On the eve of the Great Schooner Regatta, the fleet holds a smaller but perhaps more beloved race in dinghies. Dennis read the simple but quirky rules aloud from a paper scroll. No captain of a windjammer was to be involved in any capacity (after the rules were read). There were two classes, sailing and rowing. The course consisted of a circle around the anchored fleet. Costumes were recommended. All projectiles must be biodegradable. And definitely, absolutely no nudity was allowed. Dennis’ delivery had everyone laughing by the time he ceded control of the operation to his first mate.

Our crew chose to dress in a salty version of business casual, complete with neckties and ID badges, which they referred to as “ketch professional.” (Angelique is the only ketch in the fleet of schooners.) Everyone helped lower the dinghies and we climbed down, armed with oars and two bags of marshmallows. The race itself ended up being equal parts rowing and food fight. By the end, it seemed everyone was an old friend or—occasionally—old rival.

The storm provided some downtime for the Angelique’s crew 

The storm provided some downtime for the Angelique’s crew 

By the time we returned to Angelique, still combing soggy biscuit chunks from our hair, twilight was falling and I began to get a sense of what life aboard ship was usually like (the dinghy race’s antics are not the norm for this fleet) with passengers scattered about the deck chatting in hushed tones or curled up with books. On one of the schooners, someone was playing a fiddle. Not a single digital screen lit up the night. It was, perhaps, the single most peaceful place I’ve ever been.

As people started heading to bed, Dennis disappeared from one of the small groups on deck and returned a few minutes later with a flashlight. He handed it to me, having noticed that I was squinting and holding my journal about six inches from the tip of my nose as I attempted to finish an entry that read: “At first glance, it could be 1850—an evening frozen in time. Few people remain on deck now, silhouetted against the last blush of orange to the west. It’s just 2130 but out here you live by the sun, I guess. I’m going to walk about the ship a bit before I turn in for the night. When I wake up, it’ll surely be 2018 again, but I just want to stay here for a few more moments.”

That night I slept uneasily, probably because I was in an unfamiliar place and sharing a cabin with a stranger (a very friendly one, but a stranger nonetheless). Wide awake at 0300, I went topside to enjoy the cold morning air and was visited briefly by Dennis who joined me on deck to inform me that I was over an hour too early to see the sunrise. He squinted over the stern. We’d swung around during the night and the dark shape of the schooner Heritage loomed unexpectedly close by. Dennis took stock of the situation, deemed it all fine and returned to bed. I waited for the sunrise.

The fleet creates an impressive silhouette against the sunrise over Islesborough

The fleet creates an impressive silhouette against the sunrise over Islesborough

The first item on the official agenda that day was a captain’s meeting aboard Victory Chimes. Dennis is charismatic on his own, but when all the windjammer captains get together, they’re a force to be reckoned with. The meeting was more laughing than talking, though there were also the more serious matters of fleet distribution, course and inclement weather to discuss. Eventually, it was decided that the start would be postponed until the rain cleared and the wind calmed. However, back on Angelique, neither the passengers nor the crew seemed to mind the delay. Instead, they settled in for another cozy, peaceful stretch of drinking tea, reading, knitting and plucking away at the guitar.

Finally, when the rain had slowed to a drizzle, we got underway. Passenger participation is strongly encouraged aboard all the windjammers, and nearly everyone on Angelique lent a hand in hoisting the sails. As we approached the start, the entire fleet of schooners circled, proudly displaying their graceful lines as passengers snapped photos. In fact, this would be the closest view we would have of the other boats and for good reason—they have an understandably wide turning radius and any evasive maneuvers must be made well in advance.

In other ways, however, Angelique was just like every other boat I’ve ever raced on—the constant chatter about who’s likely to be over the line; the narrowed eyes tracking the competition to confirm that, though they had better boatspeed, we could point higher; the frustrated groans as the wind filled in from the other side of the course, the one we hadn’t picked. It all felt so familiar despite the massive scale. Within an hour, the fleet had scattered until the other schooners were specks on the horizon, but Dennis kept tabs on them like it was an Opti race.

Because of the length of the course and separation of the fleet, most of the passengers enjoyed the day the same as they would have if it had been any other point-to-point sail. And when we finished an unimpressive third in our class, Dennis was the only one who seemed disappointed. As far as everyone else was concerned, we’d just enjoyed another lovely day on the water and that was that.

As we crossed the finish at the Rockland Breakwater Lighthouse, however, I also found myself having to contend with a feeling of disappointment of an entirely different sort—the result of the knowledge that once anchored, I’d be headed back ashore and on my way home. I was suddenly, inexplicably sad knowing I would have to leave the sanctuary of that windjammer and return to the world of emails and news feeds. As I bid my new friends farewell and climbed down into the dinghy, I already missed Angelique’s timelessness. 

Ed Note: For more on Maine’s windjammer fleet, visit

Photos by Lydia Mullan

December 2018



A New Era for Sailing Program Safety

As states begin to lift restrictions on gathering and marinas open back up, many sailing programs are still wary, especially since sailors from different households will necessarily be in close quarters, whether on their boat, in a launch or at a yacht club. Most will not be more



Zipwake Series S, the world's first inexpensive dynamic trim-control system, incorporates a state-of-the-art family of durable, fast-acting interceptors. The system is fully automatic, and is designed to significantly enhance performance, fuel economy, comfort and safety when more


Safety Culture Starts with the Skipper

Sailing might not be the first pastime that comes to mind when you think of extreme sports, but that’s not to say risks don’t abound. The Cruising Club of America tackles many of them head-on in their newly released guide for skippers, Creating a Culture of Safety: The Skipper’s more


Boat Review: Beneteau First Yacht 53

Luxury performance-cruising isn’t entirely new. You can go fast and still be comfortable. You can even race if you make the right tradeoffs—or so says Beneteau, which recently launched its First Yacht 53, in the process also reinventing the company’s “First” brand. Design & more


Cruising: Birds of a Feather

One of the neatest things about sailing offshore is the other lifeforms we encounter. We smile when we see flying fish skimming over the surface of the sea. We cheer when dolphins leap and dance in our bow waves. We are duly reverent when mighty whales sound and spout, and more


Pirate’s Cove Billfish Tournament

This Spring has felt a bit like a slow day of fishing but it’s almost time to time to Bait…and Switch. The Pirate’s Cove Billfish Tournaments offer something for every member of your crew. Exceptional fishing, fun times with family, old friends and new. Our run is short, our more


Tusk by Spyderco

Spyderco's Tusk knife combines a blade and marlinspike to create a multitool perfect for marine use. Made with corrosion resistant materials like titanium and LC200N steel, a nitrogen alloyed steel, and Spyderco-exclusive locking mechanisms, this knife is one of the toughest more


Italia 11.98 Performance-cruiser

This past winter, SAIL principal editor, Adam Cort, checked out the new Italia Yachts’ new 11.98 performance-cruiser at the boot Dusseldorf show in German, and says he can attest to the fact it’s a boat more than worthy of the attention of North American sailors. Available in more