A Cruising Guide to the MAINE COAST
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Casco Bay

Cape Elizabeth to Cape Small


Casco Bay: Cape Elizabeth to Cape Small

Casco Bay is where the Atlantic coast, tending north all the way from Florida, turns a sudden corner and breaks out in a flourish of islands. The great sand beaches of Maine’s southern coast end abruptly and rocky promontories and ledgy islands begin.

As the early explorers reported, there are hundreds of islands, large and small, in Casco Bay. Once known as the Calendar Islands, one for every day of the year, they are the peaks of three parallel ranges whose flanks are drowned in the bay, the valleys between gouged by glaciers that stood a mile thick on this land 13,000 years ago. Thus Great Chebeague Island, Long, Peaks, and Cushing are the extension of Merepoint Neck. Cliff Island and Jewell are remnants of Harpswell Neck. And Halfway Rock is the farthest tip of Orrs and Bailey Island.

The valleys between the ranges are now the great bays and sounds that make Casco Bay so interesting—Hussey, Luckse, and Broad Sound in the middle; Maquoit, Merepoint, and Middle Bay to the north; Merriconeag and Harpswell Sound and Quahog Bay and the New Meadows River to the east.

Casco Bay is an archipelago of islands busy yet unspoiled, rocky outcroppings barren and rugged, beaches fine and fair. Yet it is home to a small metropolis, a busy shipping port, an international airport, and a strategic harbor. While far busier with boats and people than Penobscot Bay and points east, Casco Bay is still surprisingly beautiful and unspoiled—a superb cruising ground.

The scale of the bay is small. From Cape Elizabeth to Cape Small is less than 20 miles. In clear weather, you can see the Portland skyline from Harpswell Neck. The broadest sound is only a mile wide, and the nearest island is usually only a short reach away. Sailing through the bay, one island slides against another, their dark silhouettes merging, dividing, blades of water cutting them apart.

One of the joys of sailing here is wending your way among these islands, chart in hand. It is easy to become confused about whether red buoys should be left to port or starboard, so check the chart often. Winds fluctuate as you pass into the lee of one island or another, and the current often runs swiftly through the slots.

Unlike any place farther east, the presence of a substantial metropolitan area affects the look and feel of Casco Bay. Portland is small by most standards, but it overflows onto the islands in the shadow of the city. Most of the nearby islands are actually part of the city, both remote and urban. Little yellow-and-red ferries dart back and forth among the islands carrying summer folk and commuters alike.

Fishing boats, daysailers, runabouts, excursion boats, and cruising yachts are ubiquitous. Cruise ships come and go. A ferry departs for Nova Scotia. Tankers and container ships are pushed and pulled by tugs to their berths. There are more marinas and moorings here than farther east. But do not bypass Portland just because it is a city. This is one city that is almost made to be visited by boat.



Portland is a rare city. It is a major shipping port, the terminus of an oil pipeline to Montreal, a center of law and banking, and a cultural center. It is Maine’s largest city. Yet, somehow, Portland retains the feeling of a small village with eclectic restaurants, concerts, theaters both mainstream and avant-garde, museums for all ages and interests, a local baseball team, and historic buildings. You will probably bump into friends on the street.


Harraseeket River

Tidal Harraseeket River creates a splendid, well-protected harbor at the north corner of Casco Bay, in the small village of South Freeport. This major yachting center has almost every facility, yet it remains simple and attractive. The fabled L.L.Bean store and an abundance of outlet shopping is close by in Freeport.


Small Point Harbor

The chart shows Small Point Harbor lying to the west and north of Cape Small between Hermit and Wood Island. This would be a very uncomfortable place to spend the night. As one local put it, the chart might as well label it “Open Ocean.” A “Harbor” it may be, but certainly not a recommended one. The real harbor at Small Point is Cape Small Harbor.