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A cruiser burdened by the demands of life on shore is off to the islands

By David Roper
For Points East


I wanted to get rid of him. Always sitting there on my shoulder, that horned Demon of Responsibility just wouldn't get off. As I walked down the street to the sea, oars under my arms, headed for the two-week cruise to Maine that I wait 50 weeks for every year, I tried to push the nagging little squirt off. I tried to shove him and the exigencies of what would soon be a former life to the back of my mind.

Stop thinking about it. You can pay the copier lease when you get back. Only a $5 late fee. Health insurance is paid. Mortgage is paid. Computers are backed up. Just get out of here. Walk faster. One more block to the dock, a short row out to Chang Ho, a flip of the mooring pennant, and you'll be immersed in that world you wait all year for. The little Demon will have no audience out there; he'll drown in all your attention to cruising. And he'll be totally disoriented if you cruise only to islands, away from the responsible mainland life in which he thrives.

Only to islands...hmmm. The thought of spending a couple of weeks cruising Maine waters without ever touching the mainland seemed appealing. I've always loved islands. As a child growing up in Hingham, Mass., I spent countless hours rowing out to Sarah, Langley and Ragged Islands in Hingham Harbor. There, I'd let my 10-year-old imagination take over; I'd be a bold explorer, the first ever to step ashore. I'd work my way over huge boulders and the cavern-like spaces between them, and up onto the island fields. I'd look for places where there might be buried treasure. I'd plan a place to build my fort, with secret access and a clear view of any intruding forces. Perhaps I'd even find myself taken by surprise by a few pirates, whom I'd fight back with my sword, often a stick of driftwood.

As a teen-ager, I returned again to those islands, with the girl of the moment, but this time for different reasons and with different hopes.

Years later, my wife and kids and I began renting a log cabin on Baker's Island in Salem Sound. Commuting to and from work on my Cape Dory 25, Chang Ho, sailing the three miles back and forth to the island each day, was one of the most refreshing experiences of my life. Upon my return to the island each evening at about 7, I'd row ashore, climb the ladder up to the old wharf, and head for the cabin on the other side of the island through the winding wooded trails. Often I'd hear the shouts and laughter of my 5- and 6-year-old-children as they ran down the trail to meet me. I was the returning bread earner, and I felt transported back in time, like some character out of a Thomas Hardy novel.

Reaching mid-life crisis age, with my kids now teen-agers, I really wanted another island adventure. Chang Ho and I had been to Maine and back from our homeport of Marblehead many times, but never had we felt constantly removed, away from the omnipresent shore life of cars, paved roads, and machine-made noise. Besides, this time I really wanted to be alone for awhile. Being alone and not lonely is a joy. And being alone cruising is really special. In the words of Robert Louis Stevenson: "They say it scares a man to be alone. No such thing ... What scares him worst is to be right in the midst of a crowd, and have no guess of what they're driving at." There'd be no crowds this trip.

According to the Maine Island Trail Association, a wonderful member-driven, non-profit (www.mita.org) dedicated to promoting island access by small boat while assuring island conservation in a natural state, there are about 3,000 islands off the coast of Maine. Only 170 are inhabited, and many of these only seasonally. Clearly, there's a lifetime of islands to see and explore. Nesting birds, bald eagles, seals, and wonderful island social and commercial histories are enough to keep most any explorer's interest.

I've discovered amazing primordial pine forests on Ragged Island/Criehaven, deep caves on the ocean side of Harbor Island, old abandoned trapper shacks (with old rusted outboard motors from the 1940s still inside) way up the Little Kennebec River past Roque Island, and old unmarked graves on the islands off Two Bush Channel. The wonders of discovery go on and on. So let's get started on our way east with island stop number one of this all-island cruise.

Off the Wind to Island Stop 1: The Isles of Shoals.

It's called Down East because the prevailing summer wind makes it a downwind sail, and in this case the wind was indeed in my favor as Chang Ho and I reached past Gloucester, then hardened up a bit rounding Thatchers Island and Cape Ann. There's something about that turn. You go from the j.v. to the varsity at that turn Ð suddenly there's the feel of real ocean under you. Things get big real fast. The swells, the empty horizon, the lump in your throat as you suddenly feel somehow alone, looking east, towards Europe.

Yet, if your first night is the wonderful island group called the Isles of Shoals, you only have about 16 miles left to go. Just 10 miles out from Portsmouth, N.H., this is a delightful island stop, and only a 7- or 8-hour sail from the Boston area. Pick a weeknight if you can; it will be less crowded. Entry is easy from the northwest. Soon you'll be surrounded by the rocky outcroppings and stark landscape of the three islands that, except from the northwest, surround Gosport Harbor. Upon arrival, you'll immediately feel a sense of remoteness. The water is clear. The only sound is the wind and waves.

Try to grab a vacant mooring, preferably one tucked around the corner in the cove between Star and Cedar Islands; that gives you somewhat of a lee in the event that it blows up from the northwest. But if you do take a mooring, keep someone aboard who can move the boat. Remember, it's not your mooring.

If you can't get a mooring, anchor near the middle of the harbor area (there's a 21 foot spot amidst the much deeper water), not too close to the breakwater, and let out plenty of scope. You may have to try a couple of times to get a good set, since there's kelp on the bottom. But I've anchored and held well in some good northwest breeze with a Danforth. Keep a good anchor watch. If the wind does come real strong from the northwest, cruisers can always take refuge on the other side of the breakwater between Cedar and Smuttynose, anchoring in its lee.

The island history is captivating: murder, romance, Vikings, pirates Ð all the good stuff. Here's a quick summary, according to both Don Johnson ("Cruising Guide to Maine, Volume I") and Taft/Rindlaub ("Cruising Guide to the Maine Coast.").

Vikings were the first Europeans to visit, arriving between 900 and 1100 A.D. Then came explorers and fishermen from France, England and Portugal to harvest the cod. It is said that the name Isles of Shoals comes from the fact that there were so many cod that they shoaled like baitfish. Early cod-fishing communities sprang up on Smuttynose and Appledore Islands, two of the larger islands in the group. To put it mildly, it was a stark existence for those early settlers. To really get a feel for the place back then, read "The Weight of Water," a novel by Anita Shreve. Isles of Shoals is the book's setting, and it's a great read to get you in a special frame of mind. Read it and let your imagination take over.

On Star Island is the former Oceanic House, once a great hotel and now a privately run facility. It looks like an island-based version of the hotel from Stephen King's "The Shining." Depending on the times, you may or may not be greeted warmly about landing on Star (you'll find out real quick as you approach the dock), but it is the site of some dramatic history. For example, Robert Carter wrote in his "1858 Summer Cruise on the Coast of New England," "Early in the old Colony times, the Indians from the mainland made a descent upon the islands, and killed or carried off all the inhabitants except a Mrs. Moody, who hid herself under the rocks with her two small children. As the Indians combed the island, the unhappy mother, unable to keep her infants quiet, killed them with a knife to prevent them from crying."

Maybe you should stay aboard.

My favorite island is one you can land on for sure, however. And it's loaded with history. Smuttynose is open to the public and has a nice dinghy landing spot in Haley's Cove on the southwest side, with a small beach behind a barely discernible old breakwater. Ashore you'll find some trail maps, some printed history, a small caretaker cottage, and some trails.

Capt. Haley of Haley's Cove was an industrious man who, in the mid-1700s, built a saltworks, windmills, blacksmith and cooper shops, bakery and even a brewery. At first, he may not have believed the legends that pirates such as Blackbeard and Captain Kidd once stopped here. But, when he later found four bars of silver buried on the island, he may have changed his tune. It was with these proceeds that he built a breakwater that connected Smuttynose to little Malaga Island.

All in all, Isles of Shoals is a five-star stop, a great start to an island cruise going East, and one that positions you for an early-morning take off for Casco Bay.

Time to climb into that bunk and get some rest, because next month we're leaving at dawn for the long, relaxing sail to two little-visited island favorites of mine near Cape Elizabeth and in Casco Bay.

Marblehead, Mass. sailor David Roper now explores the coast on his new Independence 31 sloop.



Published August 2001

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