Our Favorite Maine anchorages


Serenity at Bunker Cove, just inside the western end of the Roque Island Thorofare. Points East file photo by Roger Long

By Roger Karlebach
For Points East

I have cruised Maine only four times so far. Once was for three and a half weeks with a club on our old Tartan 34. The other visits, ranging from 25 to 90 days, were on our Saga 43 Ilene. All told, we’ve had only about 180 nights during these visits.

Some of them were necessarily spent in transit between our hailing port, the Harlem Yacht Club in Eastchester Bay (at the extreme western end of Long Island Sound) to the Maine border. This transit could be done in two or three days nonstop, overnight, but we tend to take at least a week, enjoying ourselves – and Rhode Island and Massachusetts – at the same time.

And because the thrill of cruising is not confined solely to the pleasures of the sea – sailing all-day/every day – we enjoy some lay days in Maine. All told, we have been in only 75 Maine anchorages and ports. Our go-to cruising guide – “A Cruising Guide to the Maine Coast,” Sixth ed., 2017, by Hank and Jan Taft and Curtis Rindlaub (T&R) – describes 280 places. Our cruising visits, by region (a total of 75), as compared to regional entries in Taft and Rindlaub (a total of 280) can be seen in the Ilene/T&R scorecard table on page 39.

In his excellent book, “Cod: A Biography of the Fish that Changed the World” (Vintage/Ebury,1997), Mark Kurlansky claims that America was not discovered by Columbus. Rather, based on their drawings of baccalà drying on racks on land, he posited that it was Portuguese fishermen, several centuries before Columbus, who discovered the cod-rich Atlantic coast of America. However, being fishermen, they kept their secret.

Well, we don’t fish. So, in Part 1 of “Our Maine Favorites,” in this issue, and Part 2 in the next (June), I will divulge my “secrets.” They are arranged in the order of a return trip southwest, from the farthest one Downeast to the southernmost off the Maine/New Hampshire state line. Disclosure: We have visited all of these places, but we haven’t sailed this precise route in the order presented.

Roque Island’s Great Beach

This is a long day’s sail past Bar Harbor, and few folks go this far Downeast. It’s worth the trip. The island’s Great Beach is an amazing, perfect, natural crescent, one mile from point to point. It is exposed only to easterly winds, which are blocked by a series of small islands. The lagoon-like configuration suggests an ancient volcanic cone that has not yet sunk down to, or below, sea level.

The island is privately owned and posted above the beach, but visitors are welcome to dink in and stroll the beach, which is sandy except in sections where it is pebbly and rocky. Alas, unlike such idyllic lagoons in the tropics, the water temperature here is not conducive to swimming, at least for us. There may be some houses on the island, but they aren’t visible from the boat.

The nearest entrance is from the southwest via The Thorofare, which runs between Roque Island and Great Spruce Island. It is narrow, with a few twists before it opens up into the beautiful lagoon. On our two visits here, we were one of only four and six boats, respectively, in this huge anchorage, and there’s room for hundreds. On both visits, we shared food with new friends on other boats. In one case, we were actually introduced to our new friends by their big Portuguese waterdog. They had guitar, banjo and voice, and we sang along.

In case the wind is predicted from the east, the island is shaped like an H, and the northwest cove, opposite Great Beach, is also large and sheltered, though we haven’t visited that side yet. Also, except by dink, we have not been in Lakeman Cove to the northeast or Bunker Cove off the southwest side of The Thorofare. Either of these would provide even better protection in a blow, but the majestic proportions, beauty and social life of the Great Beach has won us over.

36 miles to Winter Harbor

On the east side of wide Frenchman Bay, about 5.5 miles from the highly commercial and tourist-infested Bar Harbor, lies the relatively pristine Winter Harbor. Our second cruise to Maine included a week with a club that had scheduled a night here, which got drowned out by a rain-day. The wooded scenery on the way in is beautiful, as is the elegant, old, comfortable clubhouse overlooking its mooring field. The launch operators will give you a ride into town, a mile away, as will members seeing you walking there.

Greater Winter Harbor has three coves, like a three-fingered glove. In the northwest corner is Sand Cove, where the club is situated, followed by Inner Winter Harbor, and then Henry Cove to the east. There are a few restaurants, a supermarket and a hardware store.

We usually trust to luck rather than try to get to a port when “events” are scheduled. But our visit to Winter Harbor coincided with their 56th Annual Lobsterfest. Lobsterboats are built for rugged durability and reliability, not speed, and the work is rather lonely out there. But we saw about 15 classes of them drag racing, with great camaraderie, past our dink in the morning. No one got hurt and no one blew an engine.

The racing was followed by a lobster dinner: two lobsters, corn on the cob, coleslaw, chips, a beverage, and a huge slice of blueberry pie served in the firehouse: $25! Then the crafts fair and later a parade and fireworks.

The club is proud to be the home of the “oldest complete, continuously raced fleet of sailboats in the country.” Nine Winter Harbor 21s sit on moorings overlooked by the clubhouse. The club has an advantage over my club, the Harlem Yacht Club. Harlem is a commuter club, with members spread out up to 50 miles away throughout the New York metro area and its suburbs. A glance at Winter Harbor’s membership directory shows that its members have homes throughout the United States, but they all have summer homes in Winter Harbor. And they are very hospitable to transient cruisers.

18 miles to Somes Sound

This sound is the long fjord-like bay that cuts deeply into the heart of Mount Desert Island (MDI) from the south, just west of the busy and more commercial Northeast Harbor. You enter the sound from “The Great Harbor of Mount Desert Island,” at the confluence of Eastern Way, Western Way and Somes Sound. You then go another four miles north before transiting a narrow but well-marked passage into Somes Harbor, at the head of the sound, to Somesville. Somes Harbor is about as well-protected a place as you can find. It is no wonder that the island’s first settlement was made here.

There is room for several boats to anchor, but we’ve always taken a vacant private mooring; the cruising guides say this is permitted. One time a man rowed past in a dink and said: “Excuse me, sir, but you are on a mooring in the 300 series, which are designed for boats of less than 40 feet; you will be more comfortable on one of the 400-series moorings.” We thanked him and took his advice. Another time, we asked a gentleman which mooring we should take, and he gave us the use of his car for the day.

From the mooring field or anchorage it’s easy to dink in, and then there is a 200-yard walk to the main road. On that road, one of MDI’s best services passes frequently. By changing from one free bus to another, at designated transfer points shown on the free bus maps of the island, one can go anywhere. We have bused to Southwest Harbor, with its library and Easy Side Diner, which is charming and delicious, as well as family owned and operated. My only mistake there was eating so much that I didn’t have room for the home-made blueberry pie, so we had to go back!

Southwest Harbor also has the largest collection of marine services in the area. The bus also runs to Northeast Harbor, from which the beautiful Asticou Gardens can be toured. Bar Harbor is for you if you like to shop, look at other tourists, or take a kayak, bicycle or mountain climbing tour, all of which originate there. There are no real restaurants in Somesville, but we go there for the summer-stock Acadia Repertory Theater, about a mile’s walk from the dinghy dock. We have seen three well-done plays there, and it is a significant motivator for the selection of Somes Harbor.

Another fine feature in Somes Sound is Valley Cove, an anchorage area set off a bit into the west side of the sound, about two miles up from the mouth. It is a pure anchorage, with no structures, and it offers a wonderful short hike/climb up to the 284-foot peak of Flying Mountain via the “mountain route.” From the top, you’ll have a clear view of the entire southern part of MDI. You can return to your beached dink via what we call the “valley route.” The hike can be done in a few hours, and we sometimes spent the night on our hook.

In Part 2, which is scheduled for the June issue of Points East, I will resume my commentary of our favorite Maine cruising spots, starting with Frenchboro Long Island, just 16 miles south of Mount Desert Island, all the way southwest to the Isles of Shoals, some 50 miles from Casco Bay, off the Maine/New Hampshire coast.

Of course, some of our future destinations may be better than many we’ve already visited. Right now, on the next Maine cruise, I’m thinking of going up the Penobscot River to Bangor. But, we are reminded, let’s not get ahead of ourselves.

When not sailing, retired attorney Roger Karlebach lives in New York City with his wife Lene and their two cats. All four of them have also sailed their Saga 43, Ilene, from the Harlem Yacht Club, on City Island in Long Island Sound, south to Grenada, in the West Indies. Details of their adventures can be found at ilenetheboat.blogspot.com. Roger reports that Ilene’s summer destination will be the Canadian Maritimes, “Newfoundland, in particular, but also Nova Scotia again. We will fit this cruise into the period June 26 to Sept. 28.”

How we think: The rationale aboard Ilene

First, “best lists” are inherently flawed by the author’s biases. We eschew places where the attraction is nightlife, bustle and shopping. Taste is subjective and personal. The Romans had a saying: De gustibus non disputandem est. In matters of taste, there can be no argument.

In other words, if I like A best and you prefer B, we are both right. We are each entitled to our respective tastes, and there is no reason for an argument. Heck, as an attorney I argued for a living. Now I don’t have to. But equally important is that to name the best one must have visited the rest. And few of us amateur cruisers can claim to have done so.

Our harbor choices: In Taft and Rindlaub, I counted only those places from the Isles of Shoals, off the southwest end of Maine’s coast, to Eastport, near the northeast end, though Maine’s coast has more spots after that as it curves briefly to the northwest. I also only counted those to which the authors gave ratings. Other anchorage reviews have no rating “stars” for either safety or attractiveness, and they might include such comments as, “You could do it, but you’d have to be crazy to anchor overnight here.”

My count of 280 does include some places I do not consider potential future spots for us due to Ilene’s 5’ 10” draft, 43-foot length, and 63.5-foot mast height. And, of course, we have stayed more often in those places to which Taft and Rindlaub have given high marks for safety and desirability.

Often those two considerations work in opposition to each other. For example, magnificent Monhegan Island, about 10 miles off the coast, richly deserves its five stars for “beauty and interest,” and it also merits only a one-box rating for safety: “Use only as a temporary anchorage.”

As you can see from the table on the following page, we have visited barely more than a quarter of the places available. And one of our 75 places, not a favorite but adequate, is not mentioned by any of the guides. We were invited to dinner at the home of a friend who lives on the west side of Mount Desert Island. She picked us up by car from the only suitable place to leave the boat. This was on a mooring given to us by the operator of a lobster shack at a very open cove marked as Carrying Place on the western shore of Blue Hill Bay.

Roger Karlebach