Kent Island Heritage Society

Kent Island is located at 641 Dominion Rd #2703, Chester, MD 21619. It is the fifth largest island in the Chesapeake Bay. Situated 30 miles from Washington D.C., it’s easy to see why this area inspires mystery and folklore. The history of Kent Island has been filled with tales of smugglers, pirates, and even supernatural occurrences. Read on to learn more.

Legendary smugglers of Kent Island
In the 1800’s, the island was home to many smugglers who used the many waterways to bring in illegal goods. This, of course, led to many run-ins with the Navy, who patrolled the waters with several ships. One of the more infamous smuggler was John B. Purdy. A native of Maryland, Purdy was known as the “Smuggler’s General.” He was one of the most prominent and high-profile smugglers of his day. In 1875, the US government tried to convict him and his crew of smuggling but were unsuccessful. Purdy was eventually acquitted, but the trial brought extra attention from the Navy, who labeled him a “nuisance.” From 1820 to 1860, the island saw a large presence of Irish and German immigrants who brought with them the smuggling trade. Many of the German immigrants were brought to the island to work on the farms, and many of them were also involved in smuggling.

The Legend of the Pirate Princess and Her Maidservant
In the late 1800’s, the island was home to many wealthy farmers and landowners, who had large families. Among these families was the wealthy Avery family, who had three daughters: Gladys, Amy, and Sara. Gladys Avery was known for her love of adventure, romance, and the sea. She was deeply in love with a man named Robert Gilchrist, who was a wealthy merchant with a big boat. However, the two were not yet married and had to be discreet while they were having an affair. In the spring of 1884, Gladys was sailing on her father’s boat while Robert was on the deck of a neighboring boat that was owned by his father. The two boats collided, and Robert’s father suffered a heart attack and died. Robert was thrown into the water, and Gladys jumped into the water to save him. Her father’s boat was destroyed, and Gladys was severely injured. Robert returned home, but Gladys stayed on the island to recuperate from her injuries. It was during this time that the legends started to surround the pirate princess. A maidservant named Georgie was hired to take care of Gladys during her stay. Georgie was a staunch believer in the pirate legends, and she loved to tell the story of Gladys and her love for Robert. When Gladys returned home, the two started writing letters to one another. Robert Gilchrist died in 1888, and Gladys moved to London to marry Robert’s brother, Captain Richard Avery Gilchrist.

Ghosts, UFO’s and Other Paranormal Activity on Kent Island
Many residents have reported seeing ghosts, feeling paranormal activity, and seeing UFOs in and around the bay. One of the most famous legends on Kent Island is the Gator of Calvert County. The Gator is a large, mysterious creature seen all over the Chesapeake Bay. Some believe it to be an alligator, while others believe it to be a gator-man. Theories vary on what it could be, from a monster from the bay to a mythical creature from the island. The most popular story about the creature comes from a man named James Burke. He lived on Kent Island, and he was a well-known fisherman who frequented the waters around the island. One day, he was in the water near the island, and he saw the Gator, which was swimming towards him. He was so scared that he jumped out of the water, causing a huge wave to form. When he told other fishermen what he saw, they were not convinced of the Gator’s existence. However, despite the lack of evidence, many people still claim to see the Gator.

Kent Island is full of historical lore and fascinating legends. Perhaps even more fascinating than the history of the island, however, is the future that it holds for this unique part of Maryland. The island is one of the most sought-after areas for potential development in the Chesapeake Bay. Many developers hope to construct a new city on the island, giving residents the chance to live among the greenery and wildlife of the Bay. If you’d like to learn more about this fascinating island, visit the Kent Island Historical Society website to read about the history of the area, or visit the Kent Island Visitors Center for more information on the island’s natural and historical treasures.

Go to next page