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Maine Liners

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Sea-cliff hunting (and gumby sailing) along Downeast Maine

Fog thickened by the minute, and the weather radio call-ed for an evening squall. Scanning the chart, I saw Birch Harbor, a narrow bay the GPS placed right in front of us. “I’m gonna head in,” I called to my first mate, Jared Ogden, 37, a tradmaster and family man out of Durango, Colorado. He steered Capella — our 27-foot sloop — toward what I hoped was shore. The boat was big enough, probably, to weather a storm . . . were it not piloted by two landlubbers. It was mid-June 2008, and we were one day into a weeklong sea-cliff-climbing and sailing trip along the coast of Downeast Maine.

“I’ll read up on anchoring,” said Jared, leafing through Sailing for Dummies. Motoring blindly through the mist, all I could really figure was we had the cliffy Maine shoreline, studded with seaweed-covered boulders, to starboard, while to port lay thousands of miles of open ocean. We puttered for a few more minutes till we reached the back of the harbor, where the GPS said the water was four feet deep. I tried to make a tight U-turn, but when the wind broadsided us, I suddenly lost steerageway.

“Watch out!” yelled Jared. Peering into the haze, I saw the outlines of jagged rocks directly ahead. In a panic, I cranked the throttle. The boat sped up — straight toward the boulders. Between the rising tide and a building wind, I had managed to catch us against a lee shore. It looked like we’d soon be ramming into Maine itself — just as my friends had predicted.

Where Mountains Meet the SeaI proposed this trip to Jared in August 2007 in Greenland. To explore the fjordland of Cape Farewell on the island’s southern tip, we’d arranged to rent a 10-meter v-hull as a floating basecamp, though we’d somehow ended up with a 10-foot boat, a pathetic match for the area’s monster seas. Jared grew up in New York and western Mass — and was, he alleged, “no slouch as a sailor.” Reared in the landlocked Boston suburbs, I didn’t press him for details. (Jared’s sailing résumé, I would later learn, consisted of a chartered trip in the Caribbean when he was a kid, plus a few laps across a pond in a Sunfish.) Leaving Nanortalik that August, we took to sea in a dinghy overloaded with climbing gear.

If there’s one thing you’ll learn real quick about Jared, it’s that he’s completely unflappable. We first met in 1997 at the Mount Washington Valley Ice Festival, and by the time Jared left, we’d decided to team up for Shipton Spire, in Pakistan. Six months later, as darkness fell on our summit day, I was bringing Jared up to a tiny stance below a verglassed chimney. We had nothing but the clothes on our backs, a summit an unknown number of pitches above, and a long, tricky descent ahead. Still, when Jared rounded the ledge, he grabbed the rack and was off up the chimney before I could express any doubts. He’s that kind of climbing partner.

These days, Jared has moved on from the life of a sponsored climber to his own construction business in Durango. He does remodeling and builds custom homes, and is cranking harder than ever. Last season, he almost sent his first 5.14.

In Greenland, we’d made it a few miles before the engine died and we had to paddle into shore and call for help. We’d been on the water only two hours. Still, Jared loved my idea for a sailing and climbing adventure in Maine. This northernmost New England state has approximately 3,500 miles of crenellated coastland, a distance longer than California’s seaboard. Follow Route 1 and you’ll pass one dead-end road after another, all leading to random little peninsulas and coves. Start exploring, like I have, and you’ll soon realize Maine also has unlimited climbing potential. The premier spots, you’ve probably heard of: Shagg Crag, Camden, Mount Desert Island, and Mount Katahdin. But there are dozens of more-obscure areas like Big Chick, Schoodic Bluffs, the Sheep Pen, and Quoddy Head. The state has everything from 1,000-foot walls, to 5.14 sport routes, to overhanging sea cliffs.

Downeast Maine (sailors here sail downwind on the prevailing southwesterlies, to go east), the site of our maiden voyage, is the crucible for sea-cliff climbing. This wild, deeply incised stretch of New England coast has the world’s biggest tides (up to 50 feet near Eastport), strong currents, rock ledges, storms, fog, and even a whirlpool in the Bay of Fundy:“Old Sow,” so named for the bizarre sounds that emanate from its depths. It’s the largest whirlpool in the Western Hemisphere, forming as the massive tides of Paasamaquoddy Bay collide with an underwater seamount. In 1835, a two-masted schooner skippered by two brothers from nearby Deer Isle got sucked into the vortex as their mother watched from shore. They were never seen again. At times, the gyre spouts geysers 20 feet into the air.

Native Americans first settled near these fertile fishing grounds more than 6,000 years ago, but it wasn’t until the 1500s that French explorers began poking around. They called the region from Quebec to Nova Scotia and New Brunswick, and as far south as Maine, L’Acadie. The most famous of these early explorers was the sailor, cartographer, and founder of “New France” Samuel Champlain. The Frenchman ran his boat aground just off Otter Point, on Mount Desert Island (MDI) on September 5, 1604, in the heart of present-day Acadia National Park; here, he met the Wabanaki Indians, whose name for the area was Pemetic — sloping land. Dense forests of birch, spruce, balsam, oak, and maple spill off the rocky isle’s sides, with small ponds and lakes sprinkled around the fringe, as well as half a dozen villages. In the 19th century, MDI’s beauty made it a summer getaway for the Rockefellers, Morgans, and Vanderbilts. Later, thanks to efforts by two Bostonians — Harvard University President George Elliot and the textile magnate George Dorr — Acadia National Park, the first national park east of the Mississippi, came to be.

To climbers, MDI is most known for its sea cliffs, some of which rise 100-plus overhanging feet from the pumping Atlantic. All told, MDI has more than 350 routes at six different areas. Add in outlying crags on surrounding islands, and you’re talking rock enough to keep the most avid climber busy for years.

Beginner’s MindThe idea of becoming a mariner started after an expedition I led in 2005 to tiny Pitcairn Island (of Mutiny on the Bounty fame), in the South Pacific. To get there, we sailed along the Tropic of Capricorn for 600 miles, most of which I spent with my head pinballing inside a marine toilet. Nonetheless, back home, I spent many late nights sipping wine and pricing scrappy boats on eBay. My wife had suggested, most reasonably, that we couldn’t afford one. But then an old friend offered to sell me his sloop for $1. Fair enough, and because I’d recently purchased land in the fishing village of Steuben, Maine (pop. 1,200; 20 miles east of Bar Harbor), I now had a home for the vessel. For the next three years, Capella sat on stands. When Jared and I showed up in Steuben this past year, we peeled back the tarps and spent a full day cleaning her, filling the water tanks, and stowing our gear. Jared immediately fell in love with Capella. With eight feet of beam, she’s a burly 5,000 pounds, made more than 40 years ago when shipbuilders routinely overbuilt hulls. The varnish peeled off the woodwork in strips, and the blue hull could have used fresh paint, but Capella was liveable, with a galley, a small head, and a comfortable cabin that sleeps four.

I hired a salty lobsterman to tow her to the water. As the boat bobbed in the waves, we locked the mast into its stanchion and gave it a heave. We could barely lift it. I called my only friend in the area, Shaun Pinkham; 20 minutes later, he paddled over in a sea kayak from the other side of Pinkham Bay, named after his family, prominent in the area for the past 270 years. In his late 40s, Shaun is thin and wiry with sandy grey hair, glasses, and a face lined from the sun and salt air (he also happens to be a pioneering Acadia climber). Even with Shaun’s help, raising the mast was easily A4+. Still, we had the boat fully rigged by noon the next day. The forecast was marginal, but Jared decided “we” should go for it.

We set off from Dyer Bay, in Steuben, heading out to open ocean through a passage between two of the Sally Islands. Soon we found ourselves fogbound, launching off eight-foot rollers. With the low clouds, the water appeared jet-black. Jared cackled like a madman, while I remained mute. I looked back to make sure the “dink” — a 10-foot skiff — was still behind us, thinking that if we went down, we could always jump in and gun for shore.

Scared as I was, being on the open ocean with my bro was awesome. It felt a lot like climbing first had — there was just no getting rid of the butterflies in my chest. In fact, learning to sail was helping me see climbing with fresh eyes. Twenty-three years into my climbing career (and one day into my sea-captain career — unless you count the nights studying sailing books), I’d forgotten there’s nothing more fun than being on the upward portion of a learning curve.

A Thousand Islands Several tense hours later, we boxed into foggy Birch Harbor. Engine whining, we gained steerage just before that collision. As the bow came around, we passed within 15 feet of shore, in water so shallow I could see bottom. A couple minutes later, my heart still palpitating, we dropped anchor. Just like that, it was over. Jared and I sat there in the fog looking at each other, and then we high-fived . . . hard.

We cooked dinner on the swinging alcohol burner. With the chart book spread between us, Jared and I studied the route to Bar Harbor, 17 bold nautical miles that would take us around the exposed tip of the Schoodic Peninsula. The boat tossed us around all night, but I slept soundly up in the V-berth. When I poked my head out the next morning, the view was depressing. A sea of white surrounded us, and a cold drizzle came down. “We” decided to sail anyway.

Two hours later, we rounded Schoodic and set off down Frenchman’s Bay in a no-man’s land of fog. Slowly but surely, we detected a hint of blue, and then a towering thunderhead inland near Bangor. Finally, the vapor dissolved. The Egg Rock lighthouse lay to port, with a half-dozen other islands shimmering under the sun. Jared hoisted the jib, and we killed the engine. For the first time, we were properly sailing.

Frenchman’s Bay is about 10 miles by five, and is bordered on its north by mainland Maine, on its west by MDI, and on its east by the Schoodic Peninsula (its tip is a satellite area of Acadia). Here, as all along the Maine coast, the sailing is so classic because of the ubiquitous little islands. Almost every isle has a rocky outcrop or two, and a few have properly good-looking cliffs. Besides MDI, the most interesting to climbers by far is Ironbound Island, a few nautical miles east of Bar Harbor. Ironbound takes its name from its south shore, a 100-foot-max, quarter-mile cliff band iron-stained red, orange, and yellow. A few people have climbed here, and each has a story of getting run off by a gun-toting caretaker. Jared and I motor-sailed right below it, pointing out arêtes, faces, and dihedrals on road-cut-sheer granite. The routes in Acadia climb similar stone, and we motored on, not wanting to take our chances.

MDI and Fish ScalesAfter picking up a mooring, I called my friend Jeff Butterfield, owner of Atlantic Climbing School and the unspoken leader of Acadian climbers. From his office on Main Street overlooking the wharf, he said he could see our boat. At 50, Butterfield has less grey hair than I do in my late 30s. He first showed up on MDI in the mid-1970s, when virtually every cliff lay untouched. Known for his keen eye, Butterfield’s spent the past three decades systematically plucking one gem after another. His guidebook, simply titled Acadia, doesn’t include first-ascent-party information. But if it did, you’d find his name, more than any other, associated with the island’s best lines. With Butterfield and two of his guides, Alexis Finley and Pete Fasoldt, both strongmen in their 20s, we spent the afternoon bouldering on a steep, 20-foot mini-cliff on the island.

Once more, we awoke to fog. The plan had been to visit Bar Harbor, and then set off again for Quoddy Head State Park, at the head of a peninsula on the easternmost tip of the United States. Quoddy Head had a climb called Mainiac, established by Spider Dan Goodwin in the mid-1980s. Some of Maine’s best climbers had tried it and described it as nearly impossible, perhaps 5.14 — at the time of the FA, maybe America’s hardest route. More than 20 years later, Mainiac remains unrepeated. I wanted to get Jared on it, but the sail up there would take us in the vicinity of “Old Sow,” a beast best left alone.

Over coffee on deck, we decided to visit Great Head. Located on a spit of land not far from Sand Beach, Great Head is reputed to be the biggest sea cliff on the Eastern seaboard — about 120 feet max and about 500 feet wide. Its defining feature is a dark, foreboding grotto (the Cavern) gouged by eons of pounding storm tides. At least one climber has died here, caught by the tide while trying to jug out. Most dismissed the cave as choss until Butterfield, in 1985, began tapping its free-climbing potential. Routes today range from 5.9 to 5.13 on bullet-hard, pocketed granite, and typically overhang Frenchman’s Bay by 20 to 30 feet. There are two ways to access the Cavern. You can rappel, waiting for the surf to pull out and then touching down quickly, to run into the back before the next wave laps at your heels. Or, at low tide, you can make a 30-foot 5.6 traverse along the bottom. As we headed down to the traverse, we ran into another ACS guide, Greg Shyloski. “Shylo” is a super-strong climber who lives in Connecticut, working as an educator in the IT field. With summers off, he heads to Acadia to guide; whenever he’s not working, you’ll find him climbing in the Cavern.

Shylo led us over to the traverse and declared it doable. Because algae covers the sloping ledge, it’s slicker than axle grease when wet. While Shylo and Jared scampered across in their sneakers, I put on my rock shoes and chalk bag. If you slipped here, clawing your way out of the surging waves onto the sloping, barnacle- and kelp-covered rocks would be full-on. A year earlier, a climber jumped into the ocean at the nearby Otter Cliffs to retrieve a dropped rock shoe and drowned. Even in summer, the water temperature is only in the high 50s, with storm surges blowing seaweed and shells over the cliff top. On the cave’s far left, you’ll find Sedated (5.11c), the only route I’d done here and another Butterfield classic. It’s the easiest way out — something to think about before you commit, because the tide rises an inch a minute. A little farther on, Shyloski pointed out Transatlantic (5.13a), long the only free route out the Cavern’s guts. Recently, Shylo and another unsung New England hero, Dave Sharratt, established two stunning lines on the right side. The rightmost, Fish Scales (5.12d), climbs a series of upside-down fins. We couldn’t safely reach it from where we were, so Greg suggested we rap.

Down on the cave floor, I put Shylo on belay as Jared rapped in to shoot photos. The ocean pumped right below my feet, occasionally spraying my legs. If the tide came up anymore or a storm rolled in, I could easily find myself underwater. Like a lot of routes in the Cavern, this one starts with a boulder-problem crux. Higher, you have to make big clips, and if you pop with rope out, you might land in the drink. The route comes to a head at the fourth clip, where you sink shaky double kneebars and reach way out. It took Shyloski a few tries before he sacked up for the clip. Above this, the route drops to 5.11, but this day the top was wet and Shylo lowered, trolleying in as he came down. “Have a go?” he asked me.

Were the route actually 5.12d (which I doubted heavily), I should theoretically have been able to dog it. Sucking hard on the salt-laden air, I flashed the initial boulder problem and, after hanging at every bolt, arrived at the crux clip. Maybe it was the crashing surf and sharp edges, but I wussed out. Next, Jared hopped on, working through in minutes and then giving a redpoint attempt; he made it just past the crux clip but then came off going around the corner. After this, we all jugged out, the waves crashing ever higher below our feet.

Unfortunately, rain came in the next day, the cavern started to seep, and we never made it back. When the weather finally cleared, I continued Jared’s tour, taking him to Otter Cliff and the Precipice. Each night, we’d retreat to the vessel and our scotch. On the last day, the forecast looked good for more sailing, so we decided — with the Atlantic Climbing School guide Fasoldt offering to accompany — to sail back to Steuben. Since Fasoldt has a couple of Pacific crossings under his belt, it was a rare learning opportunity. That Monday was bluebird, and as we sailed back down Frenchman’s Bay, we cracked cold PBRs and listened as Fasoldt instructed us in the ways of the sea — trimming sails, taking in a reef, and how to rig a boat properly (turned out our mast was cocked and we had too much weight in the stern). We repaid him with Beta on the Trango Towers, where he hoped to head soon.

While we clocked along at five knots, I worked my way to the bow and dangled my legs over the bowsprit. Every few minutes, as the boat hit a trough, my bare feet would dunk into the green seawater. Leaning back, I gazed at the full sails overhead and took a deep breath of the salty air. Jared manned the helm, steering us on a steady course toward Schoodic Island.

Over the last week, we’d checked out one island in Downeast Maine and had barely scratched the surface. With the sea as our highway, the possibilities seemed limitless: head east into the open ocean, and in 150 miles you’d land in Yarmouth, Nova Scotia, with great cragging and bouldering. You could loop back through the Bay of Fundy (avoiding Old Sow) and explore Grand Manaan Island, with its 400-foot sea cliffs. Or, if you were really feeling ballsy, head north, around Nova Scotia up to Newfoundland, with sea cliffs (Blow-Me-Down) up to 1,200 feet. Keep the SS Scrapmaster seaworthy, I reckoned, and I could do a lot of things. With years to go before I graduated from being a rookie mariner, I knew I needn’t go too far into the ocean. Trolling along the coast of Maine, learning the ropes, looking for rocks — that sounded just fine by me.

Senior Contributing Editor Mark Synnott lives in Jackson, New Hampshire, with his wife and three kids, and operates Synnott Mountain Guides (

Acadia National Park 411:

To sort Acadia logistics, visit or Spring through fall. From Memorial Day to Labor Day, Mount Desert Island (MDI) is packed with tourists and the main cliffs are busy.

Getting There: Head for Ellsworth, the crossroads of Downeast Maine, approximately 20 minutes north of MDI.

Camping: Visit

Guide Services: Acadia Mountain Guides: (207) 866-7562,; Atlantic Climbing School: (207) 288-2521,

Recommended Routes:

Otter Cliff:Wonder Wall (5.6-5.7) — 60 feet of vertical buckets directly above the sea.

Precipice:Green Mountain Breakdown (5.9+) — a beautiful two/three-pitch crack system looking out to sea.

Great Head:Head Arête (5.10c) — at low tide, perhaps the most classic lead in all of Maine. Mixed bolts and trad with hand jams out a roof and a tricky face crux.

Eagle Crag:Determined Vermin (5.10d) — a classic sandbag. If you like your fingers attached to your hand, try not to blow the opening move. Canada Cliff: House of Detention (5.11d) — one of the only sport routes on the island and the premier route at this quiet, excellent crag.


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