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Cruising Close to Home: Maine Event

East Passsage 1 5x7

Penobscot Bay is spectacular, so learn to love the fog.

Maine is heaven on water for boat junkie sightseeing and gunkholing, and it’s never better than in Penobscot Bay. It is compact, offers variety on land and on water, and has welcoming harbors. Dee and I never had time to cruise Maine when we were both working and living in Rhode Island, but we’ve tried to make up for lost time by spending five summers there, a good part of it in Penobscot Bay.

Marina docks are available in larger harbors. However, hanging on a mooring ball or anchoring is a cruising way of life up here. Most bottoms are heavy mud with good holding. We spent an entire summer cruising Maine only going to a dock to refuel.

And the fog—I just adore the fog. Yes, it can bring visibility down next to zero. On the other hand, fog creates magical vistas as the real world drifts in and out. Colors become muted. Perspectives change. Fog only lets us see what we can. Is there anything more subtly spectacular than a windjammer ghosting out of a harbor? Radar takes care of the essentials in fog, so learn to love it and go.


We start our cruise in Rockland, Maine, a busy but easily accessible port. Perhaps Rockland’s main land attraction is the Farnsworth Art Museum with its Wyeth collection. While you’re there, you should stop in at the Island Institute on Maine Street. The Institute addresses current issues in out-island communities. Its shop and always-interesting art shows merit a visit.

Two events make Rockland a compelling stop. In July, many windjammers come into the harbor en masse, parade in and out, and then anchor for the night. Later in July, there are Friendship Sloop Days. The Sloop Day sailboats were the working boat class of Maine for generations. By day, the lovingly maintained and restored boats will race in the harbor, and by night, the boats will be displayed at the Public Landing.

Ten miles over to Pulpit Harbor in North Haven, Maine is a protected anchorage with a front row seat of windjammers that often come at the end of the week. Classic small boats are scattered on moorings, but it’s the view that is so provocative. Pulpit Rock dominates the harbor entrance. As the clouds and light play with the rock’s backdrop, Camden Hills, the view and mood seem to completely change. It’s always exquisite—it’s my favorite place.

Camden offers marked contrast to Pulpit Harbor. The harbor is busy on a regular basis. Occasionally, cruise ships will anchor just outside the harbor. There are many dining and shopping options—a good thing that gives visitors plenty to do. Load up on carbs and calories, so you can enjoy walking them off at our next stop up the Bay: Warren Island State Park.

Accessible only by boat, Warren Island is a camper’s delight. Pick up a park mooring if you can, and watch kayakers come in with their gear. At low tide, explore the shoreline for tidal pools and interesting rocks, and exercise your nature reference books. A section with exposed roots creates a fun obstacle course/maze and highlights a trail leading around the island. If you are fortunate enough to be there after it rains, you’ll find all sorts of fungi—maybe even the delicate Indian Pipe, also known as the “Ghost Plant.”

From the great outdoors, we move up to the historic, deep water port of Searsport, and enter the Penobscot Maritime Museum. The campus is within walking distance of the waterfront and occupies historic buildings from Searsport’s heyday. Displays highlight regional maritime activity from the small, dories and canoes, to the large, Searsport’s globetrotting sea captains and their ships.


If Searsport offers a good look at what maritime life was like in Maine, perhaps Castine offers the best sampling of what a Maine seafaring community looked like. It doesn’t pretend to be a preserved town. Castine simply offers visitors the opportunity to walk in a pleasant village. Make it a project to find the 100 historic markers scattered throughout the town.

No cruising boat junkie should miss a trip down Eggemoggin Reach to Brooklin and the WoodenBoat School. Anchor or pick up a mooring and then walk up the hill to the school’s shop. The school’s mooring field is a museum and a showcase of wood small craft—from an old Herreshoff 12-1/2 to a recently launched, class-built, cold-molded beauty.

The same can be said for the boats that come into the harbor for August’s Eggemoggin Reach Regatta. The display is magnificent, as is the race down the Reach. Take the inflatable out to photograph the race underway. You won’t regret it.

Stonington is filled with workboats, which makes it an interesting stop. The islands of the nearby Merchant Row are compelling for gunkholing. Take the inflatable into the harbor to collect interesting boat names and then go around the islands to look for the day’s collection of visiting windjammers. Merchant Row offers the best opportunity to hang with an anchored windjammer on any given summer day. Take your camera. The setting is to die for.


It only gets better when we take a restful break before heading home to Rockland. We like going into Seal Bay to hang with harbor seals and a few other boats. I recommend going deep into the Bay beyond the two yacht club moorings. At high tide, take the dink farther in and then cut across to Winter Harbor to find the old stone quarries. A prize goes to the one who finds the stone bench, created a long time ago by a quarry worker.

Have I touched on everything to do in Penobscot Bay? No, not at all. We haven’t seen everything. We haven’t been up to Fort George or stopped in Vinalhaven for an afternoon ice cream. There is so much more left to do. I want to go back right away. So join me. Cruise Penobscot Bay. Follow my route or, better yet, follow your whims as you become a ‘Mainiac.’