Downeast Express

Downwind sailing in the Gulf of Maine with crewman David Niewolski. Photo by Christopher Birch

By Christopher Birch
For Points East

An overnight passage from the Cape Cod Canal directly to Penobscot Bay is a fitting start for a Downeast cruise. It’s a big, bold, adventurous leap to a big, bold and adventurous place. In one fell swoop, you swap out the sand, dune grasses, and warm water of Buzzards Bay for the bald eagles, extreme tides, and spruce-topped granite cliffs of Maine.

The straight shot from the east end of the canal to Monhegan Island, and on to Tenants Harbor at the mouth of Penobscot Bay, is about 140 nautical miles. If you choose instead to sail the local route from the canal to Portland, and then on to Tenants Harbor, making all the usual nightly stops, you’re looking at approximately 190 nautical miles.

In a rough sense, the express route is the hypotenuse of the right triangle formed by the offshore and the coastal routes. The Monhegan route reduces the trip Downeast by 50 miles, while getting you there three to five days faster. The canal is used as a starting point in this example, but the same general logic holds for any other starting point in Massachusetts Bay.

We are lucky here in New England to have so many world-class cruising grounds to choose from, and Downeast Maine is among the finest of them all. Downeast Maine is also the cruise that’s most often “set aside for next year.” The principal reason Southern New England sailors get cold feet about the eastern Maine coast is the perceived time commitment required by such a cruise.

I know of two good solutions to this problem: The first, and best, is to move to Maine full-time. If you can’t pull that off, bring Maine closer to you by getting to the doorstep of Downeast Maine fast via the offshore express route.

The author rowing through Tenants Harbor with a change of crew aboard. Photo by Alexandra Burke

Prevailing summer winds usually provide fine downwind sailing on the straight line to Penobscot Bay. With an early start from the canal, you will likely encounter whales and dolphins on Stellwagen Bank before sunset. At night, you’ll be in the Gulf of Maine and beyond the sight of land. The complete lack of artificial light on a clear night provides optimal stargazing conditions. Landfall on Monhegan Island usually occurs a few hours, one side or the other, of sunrise.

On top of the mileage savings, and perfect downwind sailing, the express route places you nicely on the seaward side of most of the Maine lobster traps and buoy lines. When running at night, it’s a comfort to know that you are unlikely to snag an unseen trap. The exception is in the waters around Monhegan, where traps are abundant. If your boat’s underbody is prone to catching trap buoys and lines, you’d be well-advised to arrive at Monhegan a bit after sunrise so you can spot these obstacles.

While you won’t find much lobstering between Provincetown and Monhegan, these waters are not devoid of fishing fleets. You will be sailing over, or near, Jeffreys Ledge, Platts Bank and Cashes Ledge, all places where commercial vessels ply their trades. You can expect to see them at their work, or on their way to it, as you pass by.

I remember a news story from a few years back about a nighttime collision at sea between two Casco Bay fishing boats. One of the captains would typically drop his home mooring at o’dark hundred and catch a nap as his boat steamed out to the fishing grounds on autopilot. He would slump over his helm station, on a bed pillow for comfort.

Long story short, both boats and crews survived the inevitable collision, but the slumbering skipper was thrown headfirst through his windshield and sustained significant facial injuries. Interviewed by a local paper during his recovery, he was reportedly asked if he planned to revise his nighttime watch-keeping practices. First and foremost, he was said to reply, in the future, when settling in for a nap, he planned to lie feet-first to the helm, wearing good boots. On the express route, you can enjoy some dry Maine humor even before you get there.

Monhegan Harbor lies in the narrow passage between Monhegan Island and neighboring Manana Island. In moderate wind conditions, the passage is easy to enter from the southwest and simple to exit to the northeast. So easy, in fact, that cruisers on a tight schedule, with no time to stop, can pass right through the harbor – in from the south and out from the north – without going out of their way. Monhegan is so exactly on the line, it’s easier to go through the harbor than to pass around the island.

Anchoring is difficult in Monhegan Harbor. A tight mooring field blankets most of the harbor, and what space remains is reported to be foul for anchoring. Fortunately, whenever I have visited, an open mooring has always been available. The harbor water is remarkably clear, and I have been surprised and delighted to easily see my granite mooring block on the bottom in 20 feet of water.

When islanders are out fishing, they almost always will leave their skiffs on their moorings. Any mooring without a boat or skiff will likely be at your disposal. A quick check with the harbormaster, Sherm Stanley, can confirm the availability of a particular mooring. Harbormaster Stanley can be difficult to reach by VHF and phone. However, I have been able to find him in his office above Fish Beach, at the harbor’s edge, or aboard his black-hulled lobsterboat, Legacy, moored in the harbor.

If he’s in his office, his front and back doors are usually swung open, a signal you can note from the deck of your boat before rowing in. If you arrive in Monhegan Harbor early in the morning, pick up an open mooring, have a nap, and start your search for the harbormaster after 8 a.m. On my last visit, instead of charging me for the mooring, Sherm asked me to consider making a donation to the Monhegan Associates, a local conservation group. The arrangement suited me just fine.

If the harbormaster can’t be found at all, the kitchen crew in the Fish House restaurant, below his office, seems to have a solid understanding of the mooring field and can offer guidance.

Monhegan has much to offer. After a long night of sailing, you might want to start with breakfast. From 7:30 to 9:30, every morning, The Island Inn provides some of the finest breakfast foods and breakfasting views in Maine. Situated high above the harbor, the dining room looks out over the moored boats, and beyond to the sheep- and goat-dotted emerald slopes of Manana Island. With lobster scrambled eggs or blueberry pancakes on your fork, and this panorama laid out in front of you, you will know your cruise was a worthy undertaking. For this one meal alone, it is worth sailing through the night to Monhegan.

At about a mile-and-a-half long and a half-mile wide, Monhegan is small. A few pickup trucks are on the island, but most of the residents and visitors get around by foot, with a few tooling around on golf carts. In addition to the inn, the village also has a community church, a small schoolhouse, a post office, a small grocery store, and an abundance of art galleries.

Painting is the pastime of choice for many on Monhegan. When the weather is fair, you will see an abundance of easels stationed in front of artists of every stripe. Among notable artists who have perfected their styles on the island are Rockwell Kent, Edward Hopper, Andrew Wyeth and Jamie Wyeth.

It’s no wonder that artists come: The natural beauty of the land and sea is stunning. Two-thirds of Monhegan is protected parkland, and the island boasts over 17 miles of well-marked and well-maintained footpaths. The trails that pass White Head, on the eastern shore of the island, take you to the tops of some of the highest cliffs on the East Coast. From this vantage point, on a clear day, you can enjoy dazzling views of the Penobscot Bay islands and the mainland mountains beyond.

The inland sections of trail are mostly forested. Witch’s Hair moss hangs from tree branches, and pine needles dropped by the spruce overstory make the path delightfully springy underfoot. The southern end of the island is home to the remains of an old shipwreck. It’s an eerie sight to see, having just arrived by boat, but interesting to explore nonetheless. Keep an eye out for local architecture along your walk. The island children have a tradition of building fairy houses in the woods with twigs and leaves and mosses. Hiking maps are readily available for $1 in shops and in simple kiosks around town.

If your hiking loop takes you first to the cliffs on the east side of the island, then down to the shipwreck at the southern tip, as you return to town you will stumble upon a brewery in a clearing. Impossible, right? Just too good to be true. It’s no mirage. On Monhegan, the best things really do happen, and The Monhegan Brewing Company really is there waiting for you. The seating is outside on stumps, and the beer is crafty, cold and delicious. After a long sail and an invigorating hike, an unexpected malt beverage delivers a kingdom moment.

Dropping our Monhegan mooring, it’s onwards for some 15 miles to Tenants Harbor. Here, you will find most everything an arriving sailor could want or need. Tenants Harbor Boat Yard will supply you with fuel, water, ice, a guest mooring, and a hot shower. Down the street, you will find groceries and liquor in a small market. Just beyond that is Luke’s Restaurant, where traditional Maine lobster dinners are served on a deck overlooking the harbor. Don’t skip the blueberry pie a la mode for dessert.

The restaurant is run by local sailor Merritt Carey. Carey helped to create the Tenants Harbor Fisherman’s Co-op, which provides all the lobster to the other Luke’s Lobster locations. Carey is also a veteran of the second all-female team to compete in the around-the-world Whitbread Race (think of the recent movie Maiden), and a veteran of the first all-female America’s Cup team. In addition to keeping you well fed, she makes visiting sailors feel welcome, sending you onwards with a dose of inspiration.

One of the best things about a 36-hour sailing trip is how well you sleep for the next 12 hours. Tenants Harbor is the ideal resting spot for that deep sleep. In Maine, the mosquito, aka the State Bird of Maine, comes out to visit at sunset every day. Plan to have your outdoor activities wrapped up by then and don’t forget to bring screens for your hatches.

For the first 140 miles, Tenants Harbor was the destination for the offshore sailing portion of your trip. Phase 2 of your trip becomes the starting point of a coastal cruise. A legendary trail of cruising delight unfolds from this place: Muscle Ridge Channel, Western Penobscot Bay, Fox Island Thorofare, Eastern Penobscot Bay, Merchants Row, Casco Passage, Acadia, and points east all the way to Canada. Many of the bays and thorofares are so well protected by out-islands, you will feel like you are sailing on a placid lake.

In the open water between these spots, the swells from the Gulf of Maine roll in relentlessly. Maine is at its best when the cold crash of high surf on big rock is just on the other side of the ledge or islet that forms your still anchorage. Add a lighthouse, good berry picking, a pair of bald eagles, and an immense face of pink granite, and you will have been granted the perfect spot to drop the hook. Mistake Island, down by Jonesport, comes to mind as an excellent example, its name notwithstanding.

Exquisite yachts flock to Downeast Maine to share the water with windjammers and working lobsterboats. Wisps of fog episodically deliver ethereal dividers between sea, tree, yacht and rock, while drowning out noise. Like the fog, cell service comes and goes. Absence of service drowns out more noise. When the phone is dead, and the sun is slowly winning its fight with the fog in the rigging of the neighboring wooden yawl, you will feel like you have been transferred to a quieter time in history. E.B. White essays from yesteryear rattle around in the air in this place, his home.

Downeast Maine can be hard to leave, for two reasons: 1) Because you won’t want to, and; 2) Because, with your southerly route home, the southwest breeze may have you feeling pinned down. Don’t rush. In the fall, a northwest wind will arrive on some nice, clear, crisp day. Reach back to the Cape Cod Canal on that breeze.

Frequent contributor and friend of the magazine Christopher Birch is the proprietor of Birch Marine Inc., on Long Wharf, in Boston, where he has been building, restoring and maintaining boats for the past 33 years.