Cruising Maine, by Chance

When an unanticipated opportunity to sail Down East crops up, well, you just gotta go.

May 28, 2020
Camden Classics Cup Regatta
The Camden Classics Cup Regatta is just one of the countless visual feasts awaiting summer cruisers in Penobscot Bay. Alison Langley

The first ankle biter struck while we were a couple of miles offshore, sailing past the twin lighthouses on Thatcher Island, off Rockport, Massachusetts. One moment, shipmates Herb McCormick and Tom Famulari and I were all chill, enjoying a lazy reach along Cape Ann. The next, we were boarded by a horde of flies with fangs. We swatted with ball caps, slapped with rolls of paper, but they kept on coming in an attack that raged until sunset—and resumed at dawn on the other side of the Gulf of Maine.

Who knew battling bugs would the hardest part of a Down East passage? The actual sailing? Pure delight: All it took were 25 hours and a southerly breeze for us to be snug on a mooring in pretty Tenants Harbor, Maine, with a fine sunrise in our wake, a refreshing beverage in hand, and more than a month’s worth of Penobscot Bay adventures about to begin with family and friends.

Pulpit Harbor
A boat sets sail from North Haven’s Pulpit Harbor. Alison Langley

With a life moored in southern New England, my winter thoughts the past few years had often turned to a summer cruise along the Maine coast. But for a whole variety of reasons, time, distance and logistics repeatedly ruled it out. But then, out of the blue, the stars aligned this past July, and with minimal advance planning, the trip was on.


Our departure point was Nahant, Massachusetts, a small seaside town north of Boston where Tom and I live, and where my wife, Sue, and I had our Sabre 34, Jackalope, hanging on a mooring. Herb, who is Cruising World’s executive editor, and I had just finished putting out the annual charter issue, so we had a free spell to grab a good-weather window, which, as luck would have it, opened wide just two days after the issue shipped.

Tenants Harbor
No two sunsets in Tenants Harbor are the same. Mark Pillsbury

It’s roughly 125 nautical miles from Nahant to Tenants Harbor, or about a day’s run for Jackalope in most conditions. So while Herb drove to meet us, I grabbed a few provisions, loaded them up, and by Saturday morning at 11, we were good to go.

We motorsailed the first few miles until a sea breeze filled in off Gloucester. Late in the afternoon, with flies nipping and Cape Ann disappearing astern, we watched a steady stream of whale-­watching boats parade past on their way to and from the waters surrounding Jeffreys Ledge. Soon, they too were out of sight, and by dusk, we were well offshore, enjoying a stunning sunset, surrounded by nothing but open water and occasional patches of buoys and fishing gear.


To make things easy, we stood two-hour tricks at the wheel through the night. Just before dawn, I came up from a nap below to find Herb on the helm and Jackalope surrounded by shark fins that curiously seemed to be waving at us. They, along with a blazing sunrise, were a memorable way to begin the first day in Maine.

Harbor Market
Buck’s Harbor Market serves a memorable breakfast sandwich. Mark Pillsbury

We were perhaps 10 or so miles from a waypoint we’d set off the southern end of Monhegan Island, and it wasn’t long before we heard the beefy rumble of diesel engines and spotted the glowing deck lights of fishing boats. Maybe that was what woke the flies, or perhaps it was the warmth of the day returning. In either case, soon Tom the Slayer was back at it, dispensing vengeance in a now-bloodied cockpit.

Past Monhegan, the mainland began to come into focus: bold granite shorelines topped by evergreens. First came the outer islands—Allen and Burnt and Mosquito—and then the coast, with cottages dotting the shore. By noon, we had Southern Island in sight, and then we were past it, making the turn down the channel into Tenants. As luck would have it, several salty-looking Friendship sloops were visiting, having just finished their annual rendezvous.


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Later in the day, after a nap and a bracing swim in the 61-degree water, we dinghied ashore to Tenants Harbor Boat Yard. In the guest center up the hill, I couldn’t help but wonder what prompted the management to post a sign politely asking visitors not to shower with their dogs. At any rate, we didn’t. Instead, we made the best of the remaining daylight and took an extended inflatable tour to check out the lobster boats, work skiffs, all manner of sailboats and visiting sloops swinging on moorings. Later, we enjoyed a tasty dinner of kielbasa and beans, topped off by a blazing redish sunset and star-filled sky.

lobster traps
Lobster traps? They’re everywhere. Mark Pillsbury

The Rockland area, with Tenants Harbor nearby, is a convenient place to set up camp or juggle crew when cruising this part of the Maine coast. By car or bus, the city is about three hours from Boston, and there is regular ferry service out to the islands. Once a fishing town, the harbor today is teeming with residential and transient moorings. Ashore, there are well-stocked grocery stores, chandleries, several full-service marinas, shops, museums and restaurants. But better yet, Rockland sits at the southwestern end of Penobscot Bay, long a sailor’s playground filled with countless islands, coves and harbors waiting to be explored. During late July and August, weekend classic-yacht and full-on-racing regattas attract an array of yachts and their motherships, which move from one venue to another in an endless parade of sail.


With Jackalope’s delivery complete, Tom and Herb headed home, Sue and the dog arrived, and I shifted into vacation mode for a couple of weeks. First on the agenda: a few days sailing with my brother, Dave, and his wife, Peggy, who live just down the road from Tenants and on whose mooring we were squatters.

With the boat ­provisioned, refueled and tanks filled with water, we got a late-­morning start two days later. The breeze was light as we motored up Muscle Ridge Channel, a lobster- pot-studded waterway between the mainland and a series of off-lying islands. By Rockland, we set sail and rode a southerly sea breeze east to the entrance of the Fox Island Thorofare.

Harbor Marina
Buck’s Harbor Marina is a welcoming spot. Mark Pillsbury

The Thorofare is a busy, meandering channel that runs between North Haven and the larger Vinalhaven to the south. With the wind behind us, it was an easy run, with plenty of time to gawk at the sprawling “cottages” along either shore. Even on a midweek afternoon, there was plenty of boat traffic to keep us company. Maine is Vacationland, after all.

In North Haven, we found an empty transient mooring near the ferry dock. It turned out to be a ringside seat to an endless stream of schooners, sloops, runabouts and, of course, lobster boats, which roared past, rocking ­everything with their wakes.

A work colleague and his wife have a summer home a couple of blocks from the waterfront, so eventually we dinghied ashore and went to find them. But not before a visit to Brown’s Boatyard, where we paid our $25 rental fee for the night. Brown’s is the sort of yard you’d expect to find in a working harbor. Its rambling red buildings are filled with boat parts, machinery and projects in various stages of repair. For a sailor, the weathered wharf and yard were a visual tapestry to behold.

North Haven house
We had to marvel at the impressive porch in North Haven. Mark Pillsbury

From there, we walked a rambling route through the village to find our friends, enjoyed a cocktail on their porch that overlooks the Thorofare, then walked back into town for pizza at Calderwell Hall. The place was packed, and for the record, the food was delicious.

The next morning, we used the dog as an excuse to take a long walk along the one road that heads north out of town, and then we continued on through the Thorofare to East Penobscot Bay. It was another light-air day, but we were in no hurry and were content to reach across to Merchant Row, an island-speckled body of water between Stonington and Isle Au Haut. Even with a chart plotter, iNavX on my phone, and paper charts, it was easy to get quickly disorientated and lose track of just which rocky outcropping we were passing. Throw in a few thousand lobster pots to snag, and well, it was a navigational experience that kept everyone focused. We continued east into Jericho Bay, then swung north and eventually circled back toward Stonington through the Deer Island Thorofare.

Our plan was to spend the night in town, but of course, plans change. Instead, we met up with a friend of Peggy’s—who was sailing nearby—and dropped the hook alongside in a well-protected anchorage off Camp Island. It had been several hours since we were last ashore, and my ­attention—as well as the dog’s—was immediately drawn to a nearby rocky islet with the welcoming name of Hell’s Half Acre. Before we could get there though, a schooner dropped anchor and delivered its guests ashore. No matter, there were plenty more deserted granite knobs nearby to explore.

Schooners are a frequent sight amid the islands. Alison Langley

In the morning, the sea was glassy-calm as we motored toward the southern end of Eggemoggin Reach. That’s when we, or I should say I, snagged the first lobster pot. All of a sudden, there was a loud thunk, thunk, thunk on the hull and the diesel died. Luckily, I’d brought along a wetsuit, so I was able to dress for the occasion. In the water, the current tugged the boat and stretched the pot warp tight, so all it took was a slice with the knife and we were free. But then we began drifting along at a pretty good clip, and there were several wraps of rope still knotted around the prop shaft. The crew managed to grab a passing pot, which we used as a temporary anchor while I sawed away at the remaining line. Eventually, Dave donned the wetsuit and finished off the job while I caught my breath and kept a wary eye on the lobstermen working traps nearby. I wondered out loud what the protocol might be for meeting the missing buoy’s owner in such a situation.

The rest of the day more than made up for that inconvenient start. We emerged from the Deer Island Thorofare as the breeze filled in across Jericho Bay. Our timing was perfect, and we watched dozens of small sailboats cross our path in the Small Reach Regatta, put on by the Traditional Small Craft Association. The annual raid-style multiday event begins and ends in Brooklin, home to the Wooden Boat School and the Brooklin Boat Yard.

With a 10-knot breeze behind us, we had a long run up the Reach, jibing between Deer Isle to port and the mainland. To starboard, a couple of large schooners ghosted along the shore. Our destination was Bucks Harbor, where we picked up a mooring for the night and took full advantage of the marina’s outdoor showers.

Main map
Red dots on the map mark our straight shot across the Gulf of Maine. Map by Shannon Cain Tumino

Ironically, Buck’s Harbor Marina is now owned by a couple with the last name of Buck. Jon works in the medical field, but during summer, he manages to spend most of his time at the marina along with his wife, Jessica, and their hardworking kids. Together, they keep the place spotless and have even found time to launch a small fleet of charter boats.

Bucks Harbor, it turns out, would be as far afield as we’d go in our wanderings. Our shipmates had to get back for work, so in the morning, we sailed across the north end of Deer Island and headed for home by way of Islesboro, the long island that bisects this part of Penobscot Bay. A lively wind picked up from the south, and we were closehauled all the way back past North Haven. As we neared the southern tip of Islesboro, our timing once again proved perfect, even if our luck wasn’t. We found ourselves smack-dab in the middle of the Camden Classic Cup Regatta. Yawls and ketches and schooners, all under billowing clouds of sail, blew past us toward the windward mark just as we managed to snag our second lobster buoy. It was a scramble to get the sails down in the 20-knot breeze, and even after we got the line cut, it was too rough to think about going under the boat to pull what remained from the prop shaft. Instead, we unfurled the jib to get underway and avoid the rocks to leeward. But now, the fleet was upon us once again with spinnakers flying. They, of course, were on starboard tack, and we were closehauled on port. And yes, we had a few interesting crossings as we headed off in search of calmer waters.

Back in Tenants Harbor, I took a day to catch up on work, and our daughter, Lily, joined us. Now maniacal about avoiding lobster traps, we sailed back up Muscle Ridge Channel and caught the opening day of the Lobster Festival in Rockland. The waterfront was abuzz in anticipation of the coronation that evening of the Maine Sea Goddess.

Eggemoggin Reach
You don’t need a big boat to enjoy a sail up Eggemoggin Reach. Mark Pillsbury

From there, we headed back to North Haven to visit Pulpit Harbor, where we anchored with a tremendous view of the Camden Hills to the west. By the time the sun set, I was running out of superlatives to describe the surroundings.

Much of the rest of August, I had to work. Still, we found time for dinghy rides and daysails, and enjoyed quiet nights on the boat at the mooring. Then toward the end of the month, Dave and I made one last three-day visit to investigate the anchorages on the east side of Vinalhaven. Anchored in Seal Bay, we took the dinghy to explore long fingers of water cut into the granite shoreline. We motored deep into Winter Harbor to get a closer look at the towering granite cliffs that line it. And we spent a final afternoon and night on a mooring back at Brown’s Boatyard in North Haven.

But days were getting shorter and the weather cooler. It was time for this excellent summer adventure to come to an end. Sue and I had already decided to leave the boat in Maine for the winter rather than sailing back south, and had found a yard where we could haul out sometime later in the fall. We were hooked, and we knew it.

But as Dave and I beat our way south toward Tenants Harbor in the morning, I pondered my fall schdule and checked my phone to find the National Hurricane Center tracking multiple disturbances, any one of which might spin its way up the coast. It had already been a season filled with abrupt changes in plans, so why not the endgame too? A quick call to Spruce Head Marine sealed the deal. We’d leave the boat on one of their moorings, and they’d take care of the rest. A simple solution meant no need to worry. Turns out, aside from lobster pots and flies, staying in Maine was just as easy as getting there.

Mark Pillsbury is CW’s editor.


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