Paddling Maine’s Bold Coast

Note: this is an expert-level paddling trip. For easier multi-day trips, see 5 Weekend Paddles on  the Maine Island Trail 

People always ask me for stories of epic adventure. After a 40-year career as an outdoor trip leader they figure I’ve had some harrowing experiences that would make good tales around the campfire. However, I tell them I get paid to not have epic adventures. While I’m not forthcoming with stories of near death epics, a challenging adventure with attention to safety and prudence is also a grand narrative. Here’s one I like to tell.

For years I wanted to sea kayak the Bold Coast, the final section of the Maine Island Trail. The entire water stretches 375 miles, starting in Kittery, near  the New Hampshire border and winding up around Maine’s some 3,000 islands before coming to the Canadian border. Much of the trail has   protected coves, island campsites and accessible launch sites, as well as outfitters, water shuttles and lobstermen and women.  

Over many previous years I had section paddled the rest of the Trail.  When I started sea kayaking on the Maine coast over 30 years ago, exploring the nooks of the islands and the crannies of the rocky shore kept me coming back.  I did several multi-day sea kayaking trips every year in Maine, camping on tiny islands along the way. My memories are of the tides rolling in and out, bioluminescence sparkling at each paddle stroke, seals hauled out at low tide, rafts of female eiders with chicks, rockweed swirling in the incoming tide, and a single perfect lady slipper.  

I eventually did all the other sections of the trail.  But the rugged Bold Coast, the northeastern-most section of the continental U.S., kept popping up in my imagination as the holy grail of Maine sea kayaking.

Paddlers flock to  Mt. Desert Island and with towns like Bar Harbor, access to Acadia National Park and the fjord-like waters of Northeast and Southwest Harbors, most don’t continue north.

Starting in Machias at Cutler Harbor and stretching 20 miles to the  Lubec channel, near the Canadian border, the Bold Coast is imposing with its rugged coastline, strong currents, cold water, and foggy weather.  I had heard stories that there was nowhere to land and that the Bay of Fundy’s 20-foot tides and swirling currents would capsize boats.  Yet the siren call of that section continued to echo for me. 

My daughter Amelia and I had enjoyed paddling overnights a few times in the Lubec, Campobello, and Deer Island area. Therefore, we were quite familiar with the strong currents.  Amelia is a whale whisperer. She often begs me to return to the Cobscook Bay area to paddle with whales.  Due to her uncanny ability to know where the whales were on any given day, we have shared the water with minke and fin whales on every trip.  While we were too early to see humpbacks, the frequent sightings of marine mammals such as dolphins, gray and harbor seals, as well as whales, is an amazing experience.

So, on a weeklong family trip in the Jonesport area, I made plans for a sea kayaking day trip on the Bold Coast section. It had been gnawing at my adventure spirit for too long. The plan was for Amelia, her partner, and me to go. But at last minute, Amelia’s partner couldn’t join the trip.  So we were down to two paddlers.  Normally, that wouldn’t phase me but for this section I thought having three kayakers would be much safer.  I had read so many ominous trip reports that I considered cancelling the attempt.

Frankly, I was scared to try it with two people. Even though I’ve led sea kayak trips across the globe, a big case of imposter syndrome set in. I told Amelia it would take an exact convergence of perfect weather and the proper timing of tides. I also had the stipulation that when we got out of Cutler Harbor into the open ocean, I would do an intuition check. Then I would determine if I felt like it was safe for us to go.

Perfect Conditions

To consider embarking on the trip, I needed a stable high-pressure system to sit for a couple of days in the Bay of Fundy.  Also, I wanted a NOAA weather report predicting 5 knot winds or less.  I’ve always used Maine Harbors for all the relevant information I need.  In order to maximize riding the currents running south to north in the bay and the morning calm, I chose a day with an extreme low tide at sunrise. If we could leave on a calm early morning sweet spot, the chances for success increased.

We wanted to leave the Cutler boat launch at 7 am and finish the paddle before the tide turned against us around mid-day. We dressed for immersion, reviewed our safety protocols, and carried the proper rescue gear.  We packed food and water and arranged our shuttle to take out at Carrying Place Cove near Lubec.  Additionally, we packed extra water for ballast in Amelia’s boat.  That morning all the right conditions were in alignment. We did the predawn hour-long drive to Cutler Harbor to launch precisely at extreme low tide. The sun was just peeking up.  Hitting the timing and tide perfectly boosted my confidence that we would be able to complete the paddle. 

Cutler State Park is where both the land-based Bold Coast trail starts and the paddling version of it.

As I paddled on the glassy, sunrise tinged water of the harbor my body felt the familiarity of countless previous sea kayak trips. The faith surged into me that we would be safe. Now I was psyched for our Bold Coast adventures.

Soon, we were moving past Fairy Head where I could see tents of hikers on the Bold Coast Trail high on the cliff.  This spectacular trail offers dramatic cliff-side hiking on the Cutler Coast section.  The tide was picking up so Amelia and I paddled closer together. We watched a pod of Atlantic White-sided dolphins glide past.  These sleek animals were curious about us and surfaced many times around us as we floated along.  

Finally, they decided our very stiff kayaks were not very interesting to play with so they swam off.

Bailey’s Mistake

We continued along the coastline and confirmed the lack of good landing spots.  During the first hour of the trip we avoided the refracting waves along the rocky shore but kept within sight as we planned to check out a cove with a possible landing beach called Bailey’s Mistake. 

The story behind the name is captured in these lyrics from the song “Captain Bailey’s Mistake.”

Good friends gather round, and the truth I’ll relate,
How a cove near Lubec became Bailey’s Mistake;
There was a bold captain whose name was Bailey,
And his ship ended up where ’twas not s’posed to be.

So here’s to our captain, where e’er he may be,
A friend to the sailor on land and on sea;
Ye mariners all, weigh the risks that ye take,
Lest you be remembered like Bailey’s Mistake.

Even though Captain Bailey never found the Quoddy Narrows he sought, he did have a load of lumber in his ship when it ran aground. Conveniently, the captain and the crew built houses and settled there. Talk about making lemonade out of lemons.

Our stomachs started growling right as we rounded the head into Bailey’s Mistake.  Like the gift of our perfect paddling conditions, we were bestowed a gorgeous lunch beach.

After our quick lunch, we decided to try to catch the offshore tidal currents to get the “escalator ride” I had read about in trip reports.  But getting on the escalator is counterintuitive. Instead of hugging the shore where there is a perceived feeling of safety, we needed to venture about a mile and a half off-shore to catch the best current.  The escalator runs at a speed of about 6-7 knots.  My normal paddling speed is 2-3 knots so it’s quite a boost.

Amelia having lunch at Bailey’s Mistake. Photo by Karen Warren

We intrepidly headed out, not entirely certain we would find the fabled fast current.  But suddenly we crossed a strong eddyline and took off like a race car that had just been shifted into high gear.  We flew past lobster buoys and watched the distant coastline whisk by us.

With the escalator ride we ended up paddling the 18 miles of coastline in under 4 hours including a lunch stop.  Certainly, this was by far the fastest I’ve paddled that distance while sea kayaking on the Coast of Maine.

The Old Lobsterman

We were in sight of West Quoddy Head and the take-out at Carrying Place Cove when we saw our first boat of the trip, a small lobster skiff working near the shore.  As we got closer, Amelia yelled out “Koala Wallace!!” and took off after the boat.  I tried to follow her but she was paddling like a lunatic to reach the lobster boat criss-crossing the small bay.

I remembered a story she had told about meeting an old lobsterman named Johnny Wallace a few years ago when she and her partner Pete camped in the area. In the spirit of any budget camper, they had found a wonderful place to pitch their tent above high tide in Carrying Place Cove.  Since Johnny launched from a slice of the cove he owned, they asked his permission to camp. The old lobsterman’s answer was hilarious. “We don’t want any dope suckahs out here.  You can camp here as long as you ain’t one of them dope suckahs.”  They assured him they were not and were allowed to camp.  Over the next few days, Amelia and Pete had many amazing interactions with the codgy lobsterman.  He gave them fresh lobster and they entertained each other with stories of their different lives.

The reunion with the lobsterman who my daughter nicknamed Koala Wallace was filled with Down East nostalgia.  I cherished meeting him when we all finally landed on the shore at Carrying Place Cove. I got to hear the stories he regaled them with in the past.  

At the end of the trail is the village of Lubec.

We also celebrated the completion of our Coast of Maine sea kayaking adventure.  We marveled at how fast the current had swept our boats along the Bold Coast.  Additionally, the ever changing marine weather had given us reprieve for the morning because the moment we landed on the beach, a dense fog descended.  Had we waited even an hour to launch, it would have been an entirely different trip.

And those epic adventures people ask about? The truth is that paddling the Bold Coast the way we did it was not an epic paddle. Instead, it was a well-planned, well executed trip where we carefully unstacked each risk factor so we could enjoy an amazing day on the water.

However, sea kayaking the Bold Coast of Maine remains one of those “don’t do this at home, these are professional drivers on a closed course” kind of adventure.  In sum, plan carefully, be conservative with safety, stay on shore or bail out if the risk factors start to stack up, know what you are doing.  Don’t have an epic paddle with no stories to tell


Karen Warren

Karen Warren has spent over 45 years teaching outdoor education and leading wilderness trips in higher education. Karen documents her outdoor adventures on her website

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