When we are asked to think of freebooting ports, most imagine tropical breezes, palm trees, green water and white sand. It's doubtful that anyone in a general mix of ten people would have William Penn's charter city pop first and foremost into their minds. Too bad, really. There's a reason Philadelphia has been called by some historians "the New Orleans of the north", and it wasn't just her many drinking establishments (more, during the late 18th and early 19th century, than any city in New England) that spawned that moniker.
The land that now occupies the sprawling city of Philly was once occupied by the great Delaware Nation. In the 1620s Cornelius May arrived from Holland and built a fort on the bay of Swanendale. This place became a magnet for Nordic European settlers and by 1640 the area was burgeoning with Dutch, German and Swedish immigrants.
The English, who firmly believed that New England was no New Holland, started making inroads into the area as early as 1642 but it wasn't until 1682, when William Penn arrived with his charter, that the place became a holding of Britain. Given his charter to settle the New World as payment of a debt owed to Charles II of England, Penn was a devout Quaker with a vision. He imagined a Utopian city with broad streets, public parks, and neat housing with gardens and orchards on the private lands. He originally referred to it as a "City of Neighborhoods" but eventually settled on the hybrid Greek name Philadelphia.
From the beginning, Philadelphia's large port was a magnet for trade. People and goods came in on ships and the same cargo went out. In the early days from around 1700 until the 1720s, trade with the West Indies boomed. Rum, indigo, sugar and, slaves sailed in on tall ships from every friendly nation. Queen Anne's war in the 1710s halted much of this trade and the economic depression that followed made the city realize that independent action was needed. Small docks and boatyards sprang up. Freebooting, at first disguised as fishing or even whaling, began in earnest and the pirates in question smuggled rum first of all.
The beauty of Philadelphia as a smuggling port was it's complete lack of organization. The town fathers, too busy with civic duties to trouble with what went on over the water, did not create a central governing body for ships and goods going in and out of the port. Docks and warehouses were privately owned, an ideal situation for piracy. Well to do citizens formed "guilds" which would issue patently illegal "commissions" for freebooters who would then share profits with the investors. It was great good times until that pesky Revolution got in the way.
But Philadelphia and her people were resourceful and when the Continental Congress began handing out letters of marque in their own back yard, many of the former freebooters jumped at the chance. Because of the blockades imposed by the British, and the physical situation of her port, Philadelphia never became the privateering magnet that places like Boston and Baltimore developed into. Her port continued to grow, however, and it was from Philadelphia that Commodore David Porter sailed in 1821 to meet his Mosquito Fleet in the Florida Keys and stamp out Caribbean and Gulf piracy once and for all.
During the Civil War, Philadelphia's industrial complex and shipping capabilities contributed a great deal to the Union cause. Her now regulated dockyards shipped out men, ammunition, provision and in particular uniforms. Her newly established U.S. Naval Yard turned out sturdy ships. She was home to privateers with legal Union commissions as well as Naval heroes such as David Farragut and his brother David Dixon Porter.
Into the 20th century, Philadelphia continued to be a port of trade and a supplier of ships. The U.S. Naval Yard on Hog Island built warships for both World Wars, as did some of the privately owned yards close by. Unfortunately, her old docks and warehouses were gone by this time, but she is still an active and capable port city to this day.
Philadelphia's sailing history is often lost in a tourist's hurry to take in Independence Hall, Betsy Ross' House, Ben Franklin and George Washington memorabilia and cemeteries chock full of founding fathers. But believe me, it's worth a look at the port, the docks and yes, the cemeteries. Much of America's seafaring history still resides in Philadelphia. And some of her heroes do too. Stop by Woodland Cemetery while you're there and give my best to Stephen Decatur and David Porter. Separately though; they didn't like each other very much. So much for brotherly love.