Introduction
Boston is one of America’s oldest cities, and with that age comes layers of haunted history. From colonial battles to tragic fires, from hidden graveyards to eerie tunnels, the city and its surroundings are steeped in ghost stories. Ghost tours through the North End, Beacon Hill, and Boston Common already reveal plenty of chilling tales. But there’s something far more spine-tingling about experiencing Boston’s haunted heritage from behind the wheel—where each headlight flicker and shadow on the road may hide something more.
Driving itself can be exhilarating, but navigating Boston’s haunted roads transforms it into a true adventure. Whether you’re looking for a short, eerie detour or a longer road trip into New England’s darker legends, these haunted drives deliver both chills and thrills.
Spooky Drive List
1. Route 44 – The Phantom Hitchhiker (Rehoboth, MA)
About 45 minutes south of Boston lies Route 44, infamous for its phantom hitchhiker legend. Motorists have reported seeing a bearded man in flannel waving for a ride—only for him to vanish from the backseat or beside the road. This eerie stretch near Seekonk is one of New England’s most notorious haunted highways.
Directions: Head south on I-93 and I-95 toward Rehoboth, then take Route 44.
Best time: After midnight, when the road is quiet and unsettlingly still.
2. Boston’s Central Burying Grounds & Boylston Street
Located on Boylston Street near Boston Common, the Central Burying Grounds (69 Boylston St, Boston, MA 02116) are said to be haunted by Revolutionary War soldiers and disturbed spirits from mass graves. Drivers passing along Boylston at night often report shadows or cold drafts seeping into their cars. Pair this with a slow drive past Boston Common, where ghostly figures have long been whispered about.
3. Manual Driving Academy – Confidence for Night Drives
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4. Lizzie Borden House – Fall River, MA (~1 hour from Boston)
For those willing to take a longer night drive, head to Fall River and pass by the infamous Lizzie Borden House (230 Second St, Fall River, MA 02721). The site of the 1892 axe murders is one of the most haunted locations in New England. Driving the surrounding streets late at night often feels like something—or someone—is following you.
5. Bridgewater Triangle (Multiple Towns, ~40 miles south)
Perhaps the most famous paranormal region near Boston, the Bridgewater Triangle spans Abington, Rehoboth, Freetown, and other nearby towns. Drivers report everything from UFO sightings to phantom lights and ghostly figures on backroads. With its dense forests and rural stretches, driving through here at night is not for the faint of heart.
Proximity: About 45 minutes south of Boston.
Must-see roads: Seekonk backroads, Freetown State Forest edges, and Taunton area routes.
6. Dogtown – Gloucester, MA (~1 hour northeast)
Known as “Dogtown,” this abandoned settlement in Gloucester is surrounded by legends of witches, curses, and roaming spirits. Though most of the ruins are accessed on foot, the roads leading into Dogtown—especially Cherry Street and Dogtown Road—are lined with unsettling stone markers and an eerie, isolated feel.
Directions: Take MA-128 N toward Gloucester, then follow local signs toward Dogtown Road.
7. Extended Adventure: Salem, MA (~40 minutes north)
No haunted driving list near Boston is complete without Salem, home of the infamous 1692 witch trials. A nighttime drive into Salem, especially in October, is an atmospheric mix of historic charm and spectral chills. The roads around Charter Street Cemetery and Gallows Hill Park are said to host lingering spirits.
Distance: About 25 miles north of Boston.
Conclusion
Boston’s haunted past is best experienced on the road—whether you’re crossing Route 44 in search of the phantom hitchhiker, circling the cemeteries near Boston Common, or venturing into the Bridgewater Triangle. Every mile offers a story, every shadow a mystery.
So grab your keys, invite your bravest friends, and let the road reveal Boston’s spectral side. And if you want to feel fully confident—whether on Boston’s historic streets or its darkest backroads—you can schedule a lesson with Manual Driving Academy. Skilled instructors will help you navigate with control, no matter how eerie the road ahead feels.
