The History of Fenwick Island, Delaware

The early history of the town of Fenwick Island began when Lord Baltimore granted a tract of land on March 23, 1680, to Col. William Stevens. Lord Baltimore called the band of land a “Fishing Harbor.” In 1692, Fishing Harbor was conveyed to Thomas Fenwick, a wealthy York planter who originally settled in Maryland, but never lived at the island named for him. Thomas Fenwick lived elsewhere in Sussex County for many years. He served as a Justice of the Peace, Sheriff and Register of Wills. He died in Lewes in May 1708. Fenwick’s heirs were sired by a William Fassett. Before he was Fenwick’s future son-in-law, local legend says that Fassett entered Fenwick by swimming ashore. Whether Fassett swam from a merchant ship or a pirate ship is disputed. He later married Fenwick’s daughter, Mary, and claimed Fenwick Island for himself.

The Penn’s and Calvert’s

Originally the Delaware lands, including Fenwick Island, were know as “the lower Counties of Pennsylvania” because they were owned by the Penn Family who received a grant from the King of England. In fact, some of the lands of Delaware were also claimed by the Lord Baltimore and Calvert Family. What was originally a surveyor’s 120 mile mistake was settled by the Courts in 1803. As part of this settlement, the lands to the south of The Trans-Peninsula Line belong to Baltimore and Calvert and the lands to the north belong to Penn. The Trans-Peninsular Line, surveyed in 1750-1751, begins in Fenwick, and runs east-west for 69 miles until it reaches Taylor Island.

Trans-Peninsular Markers

At the Fenwick Island Lighthouse there is a stone marker that displays the coat of arms of Lord Baltimore and the Calvert family of Maryland on the south side, and on the north side it shows the coat of arms of the Penn family. This stone is “the oldest standing man-made object on the coast between Indian River and Ocean City."  Like the lighthouse, the stone marker has been well preserved on its elevated site. Markers were placed every five miles, save one marker, which should have been placed in the Pocomoke River. The markers were probably the same at the time of their placement but today are in varying degrees of decay. Besides the one at the Lighthouse, there are markers five miles west of Fenwick, in Selbyville, in Gumboro and in Delmar.  In Delmar, the southwest corner of the Trans-Peninsular Line meets the north-south line surveyed by Charles Mason and Jeremiah Dixon in 1760.  The Trans-Peninsular Line represents the southern boundary, which was disputed by the Penn Family and the Calvert Family for a hundred years.

In 1650, three hundred years before the U.S. Military stabilized and filled the barrier islands along the Delaware coast, there were shore breaks between the islands, allowing ships with shallow drafts to navigate into the sheltering inland bays. Little Assawoman Bay, Indian River Bay and Rehoboth Bay all had multiple opening to the Atlantic Ocean. These water passages served local planters and craftsmen who sailed their shallow Bay Boats through the channels and north to Philadelphia to market. Slavers entered these passages and unloaded their human cargo on Angola Neck in the Rehoboth Bay. The channels also worked for pirates.

Pirates like Blackbeard

Pirates used small islands and coves in the Inland Bays as camps, where they rested and unloaded their plunder before going back out to sea. Pirate life was easy in Colonial times as there was no law except for town constables. South of Philadelphia there was little military presence. So, for a period of time, roughly one hundred years, Pirates along the Delaware Coast made life miserable for the local sea captains between 1650 and 1750. The southeastern colonies were home to wealthy tobacco farmers who all sent their product to England. Tobacco was a universal currency and could be used buy anyone to buy food and supplies. Many ships returning from England were heavy laden with assorted goods and payment for the purchase of tobacco. Local legend says that the pirates used Points of Cedar Island, a small and shrinking island, in Little Assawoman Bay, just west of Fenwick Town, for a staging area. Blackbeard often sailed his Corsair, Revenge into the Chincoteague Inlet. Local legend says that one of his wives lived in Chincoteague Village. Captain William Kidd moored his ship in Lewes harbor in 1699 before sailing away to Madagascar. Fortunately for merchant shipping, the British Navy destroyed most of the pirates that plundered the southeastern Colonies in 1703. Blackbeard was killed in Ocracoke, North Carolina and Captain Kidd was captured in Boston, and was hanged in London.

Charles Wilson's Treasure

A colleague of Blackbeard’s named Charles Wilson was born of a wealthy family in South Carolina. After service with the Navy, he turned to pirate life in the 1730s. A local legend that says that he haunted the Delaware Coast is supported by a letter found in a steamer trunk, in an attic in Berlin in 1948. The letter from Smith is dated 1748 and is addressed to his brother. He offers a set of directions and a crude map for finding his own buried treasure on Assateague Island, just south of Ocean City, Maryland.The letter says:

“…there are three creeks lying 100 paces or more north of the second inlet above Chincoteague Island, Virginia, which is at the southward end of the Peninsula. At the head of the third creek to the northward is a bluff facing the Atlantic Ocean with cedar trees growing on it about 1 and 1/3 yards apart. Between the trees I buried in 10 ironbound chests, bars of silver, gold, diamonds and jewels to the sum of 200,000 pounds sterling. Go to the “Woody Knoll” secretly and remove the treasure…”

(Assateague… The Place Across-Reginald V. Truitt, 1971).

Charles Wilson was tried in the Admiralty Court in London and hanged. George Wilson died a pauper. There have been many unsuccessful attempts to find the treasure.