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I distinctly recall the first time I laid eyes on Maine’s Penobscot Bay. I was making my inaugural visit to a friend who had moved to a rustic spread just inland from Camden and Rockland. The drive from Boston took me from the heavy vacation traffic of Interstate 95 down to iconic Route 1 and then northeast along one of the most alluring shorelines in America.

As a young sailor obsessed with boats and maritime history, I saw that part of the Maine coast as a dazzling Disney World of decadent delights. Its craggy coves, historic harbor towns and old-school shipyards, and the hills rising dramatically above it all, embodied my ideal of what a seacoast should be: an area that takes no work to love, nor any work to find a place to enjoy cruising.

The Maine coast is divided anecdotally into four regions: southern Maine, adjacent to New Hampshire, which includes the resort town of Kennebunkport; Casco Bay, upon which the city of Portland lies; Mid-Coast, which encompasses the western shore of Penobscot Bay; and Down East, which touches New Brunswick and includes Bar Harbor.

Sunrise on the harbor in Stonington, Maine

Sunrise on the harbor in Stonington, Maine

Penobscot Bay is named for the Penobscot River, which empties into it. The bay is roughly 40 miles long and 30 miles wide. It is studded with charming mainland towns including Thomaston, Rockland, Camden, Rockport and Castine, and some 200 islands, which range in size from the larger Vinalhaven, North Haven and Islesboro to rocky humps a few hundred yards across.

Since that first visit, I’ve enjoyed the pleasures of Penobscot Bay many times, by land and by sea. Naturally, the seaborne adventures have netted the greatest rewards.

As with any cruising grounds in the northern latitudes, the prime season is July and August when the weather is friendliest. Moorings and slips can get crowded during that time, but there’s plenty of room to move. Hazards do abound for the careless, though. A hilly, rocky shoreline may be great for knee-weakening scenery, but it can be hard on the running gear if you get it wrong. The same goes for the countless lobster pot buoys and lines that trail down to the traps that collect the coveted, clawed crustacean, Homarus americanus. And short of the occasional effects of a warm Gulf Stream eddy, Maine waters range from cold as hell to frigid, which can generate fog in summer.

Lobsters on the boil

Lobsters on the boil

But those hazards are what makes Penobscot so appealing. They are a trifling for the pleasures that await intrepid cruisers.

The variety of experiences one can harvest in Penobscot Bay is legion. After awakening to the rising sun in an island cove of your own, you can try to grab a slip or a mooring in one of the small towns for a great lunch and a stroll. My favorite landside attraction is Mount Battie in the Camden Hills State Park. The overlook there offers sweeping views of the bay and islands. It’s a hike from town, but worth every footstep. On the way out, you can grab some lobsters to drop in the pot or toss on the grill. If you’re a fan of lighthouses, the bay hosts more than 15, many of which are visitable.

America’s maritime heritage is evident all along the coast. The cultural remnants of several centuries of seafaring can be seen in the many boatbuilding and repair yards scattered about the bay. Lobstermen and other commercial fishermen ply their trade year-round, and in summer, the Camden schooner fleet is out and about providing throwback views on the horizon and amid the islands.

Penobscot Bay is quintessential Maine coast cruising. As I do today, you’ll remember the first time you laid eyes on it.