Top 8 Most Haunted Bridges & Roadways in Massachusetts

The following is a list of allegedly haunted Bridges and Roadways in Massachusetts. To view my full list of ghost stories and haunted locations in Massachusetts, Click Here. And if you liked this list, be sure to check out my new book, The Folklore & Haunted Locations Guide: Massachusetts, available on Amazon!!
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​And be sure to also check out this spooky YouTube Video I made to go along with this Blog:

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#1

​Battle Road

Coordinates: 42.448040°, -71.256587°
Location Address: Battle Road Trailhead, Old Massachusetts Avenue, Lexington, Massachusetts
Battle Road is a 5-mile hiking trail in Lexington, Massachusetts, where many of the first skirmishes of the American Revolutionary War occurred between American minutemen and British military forces in the late 1700's. The historic trail is said to be haunted by the spirits of a group of British soldiers who were ambushed and killed by American patriot forces. Hikers on Battle Road Trail near dusk or after dark often report witnessing apparitions, as well as hearing the disembodied sounds of muskets being fired, and men shouting in the distance. Others report feeling a strange presence, or experiencing sudden, unexplained feelings of dizziness and nausea that subside upon leaving the area. One commonly told story is that the bodies of several British soldiers who were killed by Colonial militia forces are still buried at Battle Road in unmarked graves, however their bodies have yet to be found.

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#2

Derby Street

Coordinates: 42.521416°, -70.887007°
Location Address: Derby Street, Salem, Massachusetts
Pedestrians on Derby Street in Salem, Massachusetts often report witnessing the apparitions of former sailors and dock workers who once traveled the roadway from the nearby Derby Wharf. Although their ghostly figures are frequently encountered by motorists and pedestrians at night, their identities and the reason for their presence is unknown.

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#3

Dudley Road

Coordinates: 42.524153°, -71.299690°
Location Address: Dudley Road, Billerica, Massachusetts
Dudley Road in Billerica is said to be haunted by several different spirits, and is believed by many to be one of the most haunted roads in the state of Massachusetts. At night, motorists report witnessing the apparitions of a group of nuns belonging to the Daughters Of St. Paul Convent, who were hanged in a nearby field after being accused of practicing witchcraft in the early 1800's. One common urban legend claims that Dudley Road is haunted by another nun who was hit by a car during the 1950's while returning to the nearby St. Thecla Retreat Center. Paranormal investigators at the location also report witnessing the spirit of a former nun who committed suicide hanging from a tree.  Pedestrians walking on Dudley Road at night often report hearing disembodied voices, whispers, and screams, as well as feeling the presence of an unseen entity. Another spirit said to haunt Dudley Road is that of a man wearing old farmer's clothing, whose face appears blank and featureless.

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#4

Eunice Williams Covered Bridge
"The Deerfield Massacre"

Coordinates: 42.646536°, -72.620160°
Location Address: 26 Eunice Williams Drive, Greenfield, Massachusetts
Early on the morning of February 29, 1704, in an event that would later become known as The Deerfield Massacre, a group of three-hundred French and Native American soldiers invaded the defenseless town of Deerfield, Massachusetts, killing fifty-six villagers and taking 112 hostages. The hostages were forced to walk over three-hundred miles north to Montreal, and those unable to make the journey were executed. One such villager was a young woman named Eunice Williams, who was unable to make the journey after giving birth the previous day. She collapsed while crossing the Green River, and was executed with a hatchet by a Native American warrior in front of her husband, Reverend John Williams, and their five children. The Eunice Williams Covered Bridge was constructed during the 1870's and named in honor of the late Eunice Williams, along with a sign commemorating The Deerfield Massacre. The area is said to be haunted by the ghost of Eunice Williams, whose body was simply left at the site of her death, and whose apparition is allegedly seen by pedestrians and motorists at night. Others report witnessing her ghostly apparition in the water below the bridge, or near the dam just upstream, where many also claim to hear the disembodied sounds of a woman screaming

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#5

Harland Street
"Ghost Road"

Coordinates: 42.234264°, -71.088296°
Location Address: Harland Street, Milton, Massachusetts
Also referred to among paranormal investigators as "Ghost Road," Harland Street in Milton, Massachusetts is said to be haunted by several different spirits. Motorists driving down the old roadway at night report witnessing the apparition of a Native American tribesman named Mingo, as well as the spirit of an unidentified headless woman and her child. Residents living on Harland Street also report hearing strange, disembodied sounds, and witnessing orbs and apparitions in the swampy woodlands nearby, especially at night. At one point in time, paranormal activity in the area became so unbearable that residents hired two psychics to investigate the location, who confirmed the presence of spirits there. The investigation of Ghost Road was detailed in Robert Ellis Cahill's 1982 book, titled New England's Ghostly Haunts.

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#6

Penny Road

Coordinates: 42.445928°, -71.035826°
Location Address: Penny Road, Saugus, Massachusetts
Penny Road in Saugus, Massachusetts is said to be haunted by the ghost of a young boy who was hit by a truck. Motorists driving on the wooded roadway late at night often report witnessing the boy's apparition standing in the road, or running through the nearby woods. Pedestrians also report feeling a strange presence, as if being watched or followed by an unseen entity.

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#7

​​​U.S. Route 44
"The Route 44 Ghost Hitchhiker"

​Coordinates: 41.845041°, -71.256510°
Location Address: U.S. Route 44, Rehoboth, Massachusetts
U.S. Route 44 is a rural roadway that runs from Rehoboth, Massachusetts, to Kerhonkson, New York, and is a popular travel route for tourists looking to experience the area's scenic autumn foliage. For many years, motorists driving on Route 44 near the border of Rehoboth and the nearby town of Seekonk have reported encountering the spirit of a tall, muscular man with red hair, wearing a flannel shirt and work boots. Although the man's identity is unknown, many speculate that he was hit by a car or involved in some type of fatal accident. In many cases, drivers who encounter the man's apparition stop to offer him a ride, but note that the man disappears before entering the vehicle, or shortly after. In many instances, those who encounter the red-haired man claim to experience other unexplained paranormal phenomena, such as electronic devices malfunctioning, or car batteries dying unexpectedly. Other motorists driving down the road at night report hearing a man's voice on the radio screaming or laughing maniacally, and numerous others have reported accidentally running the ghostly man over, only to stop and find he has vanished.

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#8

Wolf Island Road

Coordinates: 41.697976°, -70.850012°
Location Address: Wolf Island Road, Mattapoisett, Massachusetts
Wolf Island Road in Mattapoisett, Massachusetts is the subject of many folklore stories and urban legends, and has earned a reputation as being one of the most haunted roadways in the United States. The location and surrounding forest were once the site of several skirmishes between British troops and Native American warriors during King Philip's War in the late 1600's. The area is said to be haunted by the spirits of troops from both sides who were killed in battle. Similarly, the apparitions of Native American tribesmen who were captured and executed by British soldiers are often seen hanging lifelessly from tree branches, and motorists report feeling a strange presence at night, as if someone or something is lurking in the woods just out of sight. Others report hearing the sounds of disembodied voices, footsteps, and screams. One popular urban legend also claims that Wolf Island Road was the site of a tragic car accident, and that the driver's ghost appears at night in a spectral Ford Mustang to chase motorists away.

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​​​​​​​​​​​​​​​​​​​​​​​​For additional information, or to see my complete list of urban legends, folklore tales, and haunted locations in Massachusetts, Click Here. And if you liked this list, be sure to check out my new book, The Folklore & Haunted Locations Guide: Massachusetts, available on Amazon!!​

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