Few could deny that Penobscot Bay is one of Maine's most dramatically beautiful regions. Its more than 1,000 miles of coastline is made up of rocky granite boulders, often undeveloped shores, a sprinkling of colorful towns and quaint villages, and views of the sea and islands that are a photographer's (and painter's) dream.

Penobscot Bay stretches 37 miles from Port Clyde in the south to Stonington, the little fishing village at the tip of Deer Isle, in the north. The bay begins near Stockton Springs, where the Penobscot River, New England’s second-largest river system, ends, and terminates in the Gulf of Maine, where it is 47 miles wide. It covers an estimated 1,070 square miles and is home to more than 1,800 islands.

Initially, shipbuilding was the primary moneymaker here. In the 1800s, during the days of the great tall ships (or Down Easters, as they were often called), more wooden ships were built in Maine than in any other state in the country, and many were constructed along Penobscot Bay. This golden age of billowing sails and wooden sailing ships came to an end with the development of the steam engine, and by 1900, sailing ships were no longer a viable commercial venture in Maine. However, as you will see when traveling the coast, the tall ships have not entirely disappeared—some, albeit tiny in number compared to their 1800s heyday, have been revived as recreational boats known as windjammers. Today, once again, there are more tall ships along Penobscot Bay than anywhere else in the country.