Boston Harbor
Destinations

Pirates, Ghosts, and DiCaprio: Secrets of Boston Harbor

On our recent trip to Boston we had the chance to go on a cruise around Boston Harbor. It was a windy, cold day, and thankfully we were able to sit indoors on our boat and look out through the window. It’s definitely a worthwhile activity for those who like to get out on the water. On our cruise we learned a little more about Boston Harbor and its history. The harbor includes (at least) 34 islands, each of which has a long and fascinating history.

Today many of the islands are part of Boston Harbor Islands National Recreation Area. Several can be reached by ferry from Downtown Boston, South Boston, or both. The harbor islands include several military bases, forts, and lighthouses, but they were also a haven for less savory elements looking for an escape from the mainland. Mental hospitals, pirates, and gambling dens have all found homes in Boston Harbor over the decades. Here are several of the Boston Harbor islands with their own secrets to discover.

Georges Island

Boston Harbor Georges Island

This small island features Fort Warren, completed in 1847 for purposes of protecting the shipping lanes of Boston Harbor. Its design was obsolete for purposes of defense almost immediately, but during the Civil War the fort became an overflowing prison for Confederate POWs. 13 prisoners died here, and the island is home to the only Confederate War Memorial in Massachusetts. Supposedly, the fort’s corridors are haunted by the “Lady in Black”, the wife of a Confederate prisoner who was hanged after disguising herself as a man to aid in her husband’s escape. It turns out that this story was made up by a local man interested in getting attention for the fort to aid in its preservation. It worked, the Fort has been restored and is one of the most visited parts of Boston Harbor National Recreation Area. I can’t guarantee that this means the island is entirely ghost-free, however.

Little Brewster Island

Little Brewster Island, Boston Harbor

One of the most rocky and far-flung islands, Little Brewster is the site of Boston Light. This is the second oldest lighthouse still operating in the United States, and the only one that continues to be staffed and operated by the U.S. Coast Guard. As such, the island is, for the most part, closed to the public, though I’m told tours are given occasionally. Nearby you can still see a couple of windswept rocks topped with cages in the middle of Boston Harbor. In Boston’s early days, these cages were where they kept the skeletons of executed pirates as a warning. A warning not to do pirate stuff.

Spectacle Island

Boston Harbor Spectacle Island

This is among the largest islands of Boston Harbor, and among the most visited by ferries. That wasn’t always the case. In the 1800s, the island was a fraction of the size and served as the home of illegal casinos offering literal offshore wagering. The police eventually shut down the casinos and for thirty years the city dumped its trash on the island. Then, when much of Boston was dug up as part of the enormous “Big Dig” construction project, all that dirt had to go somewhere. The city decided to use it cover the landfill and create a park on Spectacle Island. Today, this much-expanded island features hiking trails, a beach, and a marina.

Peddocks Island

Peddocks Island Boston Harbor

Much of this island today involves lots of creepy abandoned buildings. It is the site of Fort Andrews, an Army Base that defended Boston Harbor from U-Boats during World War II. Much of the base is still there, but it is decrepit, abandoned, and closed to the public. As such, this was the perfect spot for Martin Scorsese to film his movie Shutter Island, starring Leonardo DiCaprio. The story of the film, and the book it’s based on, involves a U.S. Marshal possibly losing his mind while investigating a crime at a mental institution on an isolated island in Boston Harbor. In reality, several different islands actually were the site of asylums and hospitals at various times. However, none of them was located on Peddocks Island.

These are only a few of the islands of Boston Harbor. There are many others with their with their own secrets to discover!