High Street Historic District

Called the most haunted street in America with 14 haunted sites in just two city blocks, including the tale of Bloody Henny and the LeCompte Curse.

High Street in Cambridge has been called "the most haunted street in the country" by Eastern Shore ghost tour author Mindie Burgoyne, with 14 documented haunted sites packed into just two city blocks. Dorchester County, with Cambridge as its county seat, is considered the most paranormally active area on the Eastern Shore, and the street's hauntings span over 340 years of Colonial violence, slave trade tragedies, maritime deaths along the Choptank River, and family curses.

BLOODY HENNY AND THE COURTHOUSE GALLOWS

The most chilling story belongs to Henny Insley, an enslaved woman from Vienna who was accused of hacking the wife of her enslaver to death with an axe. In June 1831, Henny was brought to the Cambridge Courthouse for execution. According to Burgoyne, "They just tied a rope around her neck, tied to a tree, while they had her stand on an oxcart. They put feed in front of the ox and he slowly walked away... it was a long, slow, horrible death." After her execution, children began chanting "What'd they hang you for, Bloody Henny? What'd they hang you for, Bloody Henny?" Late at night, visitors to Spring Valley Park — where a fountain now stands at the former gallows site — report hearing ghostly children's voices repeating the haunting rhyme and the sound of the hangman's rope scraping against the tree branch.

THE LECOMPTE CURSE

In 1659, French war hero Antoine LeCompte received a patent for 700 acres along the Choptank River where the peaceful Choptank Indians had long resided. When they repeatedly returned to their ancestral lands after being driven away, LeCompte took violent action. Before fleeing, the Choptanks placed a curse: "Because Antoine LeCompte was blind to the ways of peace, his sons and descendants will suffer blindness." Remarkably, the curse appears fulfilled — Antoine's son Moses went blind, as did nine of his eleven children. Over 40 LeCompte descendants experienced blindness, and an 1819 account noted that "nineteen of the living LeComptes were blind." The blindness reportedly still plagues adult males in the family today. The LeCompte House on High Street, a Federal-style brick home built in 1803 and purchased by War of 1812 naval officer Captain Samuel Woodward LeCompte in 1842, shows strange photographic anomalies. Visitors consistently capture unexplained shadow figures in the attic window, with six documented instances showing "what appears to be an outline of a person" despite being taken by unrelated photographers at different times.

THE FLOATING GHOST OF THE JOSIAH BAYLY HOUSE

The oldest house in Cambridge was built around 1750 in Annapolis by John Caile, then dismantled, loaded onto a barge, and shipped across the Chesapeake Bay. According to legend, a British redcoat ghost traveled with the house. Workers restoring the property spotted a soldier in Revolutionary War-era uniform standing in a second-story window — in a room with no floor yet installed. When they rushed inside, no one was there. The "floating ghost" has been seen in upstairs windows and the gallery for decades, perhaps still hiding because he doesn't know the Revolutionary War is over. The house also harbors the spirit of a little girl who appears in an antique cheval mirror. A woman who purchased the house in the 1990s cleaned up the old full-length mirror and placed it in her bedroom. She reported seeing "the reflection of a little girl in the mirror — a reflection that would quickly vanish, but the child's facial features were discernible... and it was always the same child." Her teenage daughter experienced a woman "slapping her feet trying to get her to wake up," and both heard phantom footsteps on the second-floor balcony. Workers also found shackles on the walls in both the attic and basement, and the Smithsonian excavated an outbuilding identified as a former slave cabin.

THE SUICIDAL BANKER

George Woolford, president of the bank building that later became the Richardson Maritime Museum, reportedly hanged himself from the attic rafters after the 1929 stock market crash. His ghost haunts the old bank on High Street. Visitors and staff report hearing footsteps pacing the attic overhead, though one skeptical volunteer attributed the sounds to the building's air handler.

CHRIST CHURCH AND THE SINGING TREE

The ancient Christ Church cemetery, established with the Great Choptank Parish in 1692, contains a yew tree more than 200 years old whose roots have encroached on the headstone of Ann Weller, who died in 1817. When the wind blows, the tree is said to sing — not melodic singing, but a humming or buzzing sound. Many believe the sounds emanate from Ann Weller herself, whose grave has been slowly consumed by the tree. When a hand is placed on the bark, the tree reportedly vibrates. Four Maryland governors are buried in the churchyard, adding to its historical weight.

MURDER AT CAMBRIDGE HOUSE

At 112 High Street, the elegant Victorian known as Cambridge House Bed and Breakfast was the scene of a violent murder. A confrontation in the foyer involved "an umbrella and a fireplace poker" and ended with gunfire. Previous owners reported that umbrellas and pokers would mysteriously go missing from the house — they attributed the disappearances to the violent spirits only after learning of the murder.

OTHER SPIRITS OF HIGH STREET

The spirits said to prowl High Street include soldiers, governors, jilted women, oystermen, an eccentric cat lady, a dying daughter, slain war heroes, murderous merchants, laughing children, and a one-legged sea captain. At Long Wharf where High Street meets the Choptank River, there are stories of pirates and phantom ships glimpsed on the water at night. Cambridge was founded in 1684 as a plantation port and became a center for the slave trade — the town pier served as the regional slave market before later becoming a stop on the Underground Railroad. This dark history, combined with the maritime deaths of countless oystermen and the violence of Colonial conflicts, has left an indelible paranormal imprint on what visitors describe as a street where automobiles are the only foreign objects in an otherwise nineteenth-century landscape.