On the first weekend of August, in a little bay rimmed by dense pines midway up the coast of Maine, you’ll find a thriving fleet of antique wooden yachts nestled temporarily in the fog. The boats are finishing up a three-day event, navigating the cold, clear, lobster-riddled waters surrounding Deer Isle. They race up the coast by day and spend each night in a new harbor, where their crews fall asleep in wool socks and down sleeping bags. Even in the summer months, the water is cold and when the sun sets, the temperatures plummet.


The boats arrive in this quiet, rural, pine-rimmed bay in anticipation of the Eggemoggin Reach Regatta, the main event that the other two feeder races build to. On each leg, more boats join the tour and more sailors climb aboard.

The coast of Maine is a jagged one, with granite peninsulas jutting out from the mainland and fencing in islands big and small. The effect this has, when navigating through the water, is one of utter disorientation. Without careful observation of the charts, it’s easy to lose track of what is an island and what is the mainland, which projects out to sea before receding back beyond the horizon. Compounding that is the fog; it is dense and can move quickly. It’s not uncommon to hear boats before you can see them, blowing their fog horn out somewhere in the mist. And it’s not hard to forget where you are entirely; to lose sight of yourself on the map.

“At once a mode of transportation, a place to stay when you arrive, and a destination in and of itself, a boat encapsulates travel like few other things.”

I’ve been lucky enough to be invited to the race for three years now, sailing on a Little Harbor 36 built in 1960. In its previous lives, the boat has won internationally-recognized races and sailed the Atlantic. Now, it’s a pristine restoration project, all teak and new canvas, still performing well and always a threat to win the Eggemoggin Reach Regatta. I, in a previous life, learned to sail in a tiny wooden dinghy called a ‘Sea Shell,’ in a gentle lagoon in Connecticut within view of my grandparents’ deck. Since then, I have sailed sporadically but never on anything large or complicated. Now, I find myself seated on the stern as we round a mark surrounded by boats twice our size.


But like sea legs, sailing is something that comes back to you before you know it. It comes back to you in the mechanical pleasure of everyone working together on a clean tack, or an efficient sail change. While it may take an expert to explain the technical side of sailing, excitement is something that can be easily felt by even the most novice sailor. It’s thrilling to hear thick canvas whipping in the wind and voices shouting instructions from across the water; to see old boats being sailed like sports cars. It’s even more thrilling to be on them.

As technically difficult as a sailboat race can be, there is a lot of time spent waiting; waiting for the next tack, or the next mark, or the next puff of wind. During this time, often riding high on the rail of the boat as it’s heeled up, I couldn’t help but imagine where else the vessel beneath me had been. At once a mode of transportation, a place to stay when you arrive, and a destination in and of itself, a boat encapsulates travel like few other things. The boat I was on had seen far more of the world than I had, and it was this, more than the wind pushing us along, or the unknown shoreline ahead of us, that made me feel as if I was simply along for the ride.

Penobscot-Bay-Maine-Jack-CallahanIf you find yourself in Penobscot Bay and are looking for something beyond sailboat racing, you’ll find plenty to do. It is recommended that you travel by boat, however, rather than by car.

To See:
The main thoroughfare in the area, Merchants Row, is a string of islands that shelters the coast and keeps the water smooth. The islands themselves are the peaks of massive slabs of granite that line the ocean floor. The deep water makes for great sailing while the dense pines stacked on the granite islands make for beautiful scenery.

To Do:
Located in Brooklin, Maine, The Wooden Boat School offers courses in boat building, on-campus lodging, and expert instruction from regional experts. The school is also the headquarters of Wooden Boat Magazine.

To Eat:
In 2011, over $46 million worth of lobster was landed by the lobstermen of Stonington, and the town is one of Maine’s major lobster ports. Lobster doesn’t get much fresher than this, so try heading down to the docks to get a good deal.


Cover photo by Joe D’Amelio from the post #RoundAboutUSA: Trip Preparation.