13 Days of Haunted Hikes in the Berkshires

By Taylor Staubach, Berkshire MacKid Assistant Editor & Berkshire Family Hikes Founder October 19, 2020

For a county as old as the Berkshires, it would be impossible not to have our share of the paranormal. With well over 116,000 acres of the region conserved for public land use, it’s also no surprise that many of these spooky encounters occurred during recreational activities like hiking. At Berkshire Family Hikes we’re always looking for inroads to get more people exploring their outdoors, and maybe a jaunt with the things that haunt our local woods is precisely the adventure you’ve been waiting for.

1. Historic Becket Quarry

This abandoned quarry in the hills is just the place for a weird walk. Rusty trucks and forgotten machinery sit deserted making it one of the more interesting hiking trails in the Berkshires. Now in a state of arrested decay, the 300 acres was once the thriving site of the Chester-Hudson Quarry, operational from 1860-1947. The wind at the quarry seems to echo with the voices of the past. The company once shipped tons of stone used for tombstones (eek), memorials, and other monuments in the area. Even a devastating flood in 1927 didn't stop operations. Until a seemingly fateful day, when the thundering resonance of machinery screeched to a halt and the last steam whistle blew on almost three-quarters of a century of granite production in Western Massachusetts. What happened? Logical explanations point to financial mismanagement and lack of capital for necessary improvements. But if you let the preserved ruins (and your imagination!) speak to you, maybe you'll hear a different story..." if the men had gone for lunch and never returned..."

456 Quarry Road, Becket, Mass

Click here to read our full review of Becket Quarry 

2. UFOs at Sheffield Park

Take a spooky stroll through the Thom Reed Memorial UFO Monument Park in Sheffield, the spot where Thom Reed, his mother, grandmother, and brother had their now infamous 1969 encounter with extraterrestrials. The quaint area has now become a destination for UFO hunters and enthusiasts of historical landmarks (the Sheffield Covered Bridge is practically next door). It’s recent feature on an episode of “Unsolved Mysteries” has helped to boost its notoriety. Strange lights, orbs and unusual shadows abound, but be sure to keep an eye to the sky!

No trails.

Covered Bridge Lane, Sheffield, Mass. 

3. Ghosts of Bash Bish Falls

Bash Bish Falls is not only the highest waterfall in the state of Massachusetts but it may also be the most haunted. Mohican legend tells of a woman named Bash Bish who was accused of adultery. As punishment, she was to be tied to a canoe and dropped down the 60-foot falls to her death. On the morning of her execution, a cloud of butterflies appeared. Surrounding her, Bash Bish had time to escape. She jumped in the falls and was never seen again.

Bash Bish had a daughter named White Swan. Shortly after her mother’s disappearance, she married. White Swan was infertile, so her husband took another wife who could have children. Heartbroken, she started to have visions of her mother. Summoned by the spirit of Bash Bish, White Swan also jumped into the falls. Her body was also never seen again.

Today, visitors claim to see the outline of a woman standing behind the falling cascades. Is it White Swan or Bash Bish?

Bash Bish Falls is also considered one of the more dangerous waterfalls in the country. A chilling 25 people have died in falls here. It’s no surprise that there may be spirits lurking nearby.

Bash Bish Falls Trail, 2.1 miles, moderate

Bash Bish Falls State Park, Mount Washington, Mass

4. Departed Spirits at Shaker Mountain

In the 1830s, Berkshire County was home to a thriving Shaker community. In 1842, the Shakers consecrated high points of holy land in which to conduct seasonal pilgrimages. The sites were chosen by Shakers guided by the holy spirit. The Hancock Shakers dubbed their holy ground Mount Sinai and in the spring and autumn, they would walk from the meeting room of the Brick Dwelling, through the woodlands, until they reached the “sacred lot” at Mount Sinai. Non-Shakers were not allowed to step foot in the clearing, but could watch from a place outside the fence.

In the center of the clearing stood a fountain stone, a monument offering the “water of life.” The location of the fountain stone is a mystery, disappearing a decade after the Shakers ceased their ceremonies here. Some experts believe the Shakers buried it somewhere on the mountain 150 years ago.

This daylong spiritual journey was punctuated by inspiring testimonies of departed spirits revealed through Shaker instruments (the dead would speak through the living), as well as songs and dances that were sacred to the occasion. “Spirit spectacles” were handed out to the Shakers, meant to give a better view of the mountain’s ghostly guests.

Observers of the “mountain meetings” describe the participants, “some were reeling and stagering; some leaping and skiping, some rooling upon the ground…”

The Shakers would return home physically exhausted and spiritually refreshed.

Tread carefully over this ancient sacred ground and be sure to bow seven times before entering.

Shaker Mountain Trail Loop, 2.9 miles, moderate. Round Trip Loop to Holy Mountain, 6.5 miles, moderate

Route 20, Hancock, Mass

5. Bellow's Pipe & the Old Coot at Mount Greylock State Park

Mount Greylock may be well known, but the forlorn ghost that wanders around the bottom of the Bellows Pipe Trail may be less so.

Long ago nicknamed the “Old Coot”, the ghost is Williams Saunders, a North Adams farmer who left his wife and children in 1861, to fight for the Union army during the Civil War.

Saunders’s was injured and after two years with no word of his whereabouts, his wife remarried a local man she had hired to help run the farm in her husband’s absence. 

In 1863, the war had ended, and a tired, bearded stranger returned home only to find his wife standing outside happily in the arms of another man, a man his children were calling, “daddy.”

Heartbroken, William Saunders retreated to the nearby woods of Mt. Greylock. He built himself a shack along the Thunderbolt Trail, living there for years, surviving by taking odd jobs on farms, including his own, never revealing his true identity.

One mid-January morning hunters found Saunder’s lying in his shack dead. They searched his papers and the mystery was revealed. Right before their eyes, a dark shadow left Saunders’s body and darted into the woods. He’s said to be lurking there ever since.

Ghost hunters in the 1930’s and late 70’s have fueled the flames of his existence with sensational photographs of the shadowy figure, but we dare you to hit the trail and decide for yourself.

Bellows Pipe Trail, 6.1 miles out and back, Difficult

Gould Road, Adams, Mass

6. Pet Cemetery at the Mount

The Mount — Edith Wharton’s former Lenox estate — has been a constant hot bed of hauntings, attracting ghost hunters and others looking for a thrilling night out.

From floating faces to inexplicable orbs, most curious are the reports of canine spirits flitting about. From a third-story bedroom window you can see the dotted hillside. Six little stone markers reside over Edith’s furry friends. They provided her with comfort through her troubled marriage, a possible nervous breakdown, a brief affair, frequent trips back and forth to Europe, and divorce.

Ghost tours always include a stop at the pet cemetery, where guides briefly retell “Kerfol,” Wharton’s story about a pack of ghost dogs who haunt a house where they were murdered, and in turn avenged their murder and the cruel treatment of their beloved mistress.

Although reports of ghostly animal activity are scant compared to other haunted happenings, visitors have caught two interesting photos, both of which can be seen by clicking the link above. 

The Mount grounds include various short trails. 

2 Plunkett Street, Lenox, Mass

7. The Devil's Altar at Wizard's Glen

Hit up this high point on Gulf Road smack between Dalton and Lanesborough. The name Wizard’s Glen links back to a Native American legend that recounts the time a shaman offered human sacrifice to Ho-bo-mo-ko, the Spirit of Evil.

According to a tale told in J.E.A. Smith’s “Taghconic,” a 1770 Dalton deer hunter named Chamberlain, had slain his long sought quarry nearby Wizard’s Glen. While Chamberlain was dressing the animal, a fierce thunderstorm suddenly arose. Chamberlain tucked the deer carcass under a boulder and sought shelter beneath another.

While waiting out the storm, a brilliant flash of lightning illuminated an unearthly celebration. Every cleft among the boulders held macabre spectres, with a Satan-like figure appearing in the center, dripping blood. Another flash of lightning and the phantoms began to chant, dance and a maiden was dragged towards the altar and prepared for hatchet sacrifice.

In an effort to save the girl, Chamberlain removed a Bible from his pack and held it out, crying the Lord’s name. A colossal crash of thunder ended the storm and the unholy spectacle, disappearing in a flash of light. Shaken and exhausted, Chamberlain went to collect his venison, and it too was gone. The giant rock became known as the Devil’s Altar Stone and the area is said to emanate an icy chill even on the hottest and stillest summer afternoons.

No marked trails, use caution on the rocks.  

Gulf Road, Dalton, Mass

8. Camp Windigo at Windsor Jambs State Forest

Take a trip to the Windsor Jambs State Forest and see what remains of a 1940’s summer camp with a now sinister reputation. Camp Windigo was in operation until the 1980’s and most former campers remember the place with fond memories.

After 30 years of rotting abandon, new rumors about the camp started to take root, a grisly tale of murder that no one can seem to verify. 

“This is a camp that may have been up in the 1980’s and is haunted by 6 little girls and a crazy woman.  The story is that a camp counselor went crazy and hung 3 girls in a barn on the property and drowned 3 more in a tub then she went and killed herself.”

Several amateur ghost hunters have investigated the story and describe mysterious shadows, orbs, and “child-sized” handprints appearing on windows. The buildings are no longer standing, but you can still walk to what remains of the camp, a short hike from the waterfall at the top of the Jambs. 

Whether it’s fact or fiction, whatever  you decide remains to be seen

Windsor Jambs Trail from River Road, 2 miles, Intermediate 

River Road, Windsor, Mass

9. Haunted Hoosac Tunnel - East Entrance 

The East Portal of the Hoosac Tunnel is located in Florida, MA, and if you dare to visit, the first thing that will hit you is the dark, damp chill.

Construction on the tunnel began in 1851. Over the twenty-three years that it would take to finish the 4.75 mile track, it would claim the lives of two hundred miners. Commonly referred to as “the bloody pit,” most died in horrific explosions, fires, and drownings. Since it’s completion, there has been no shortage of strange reports, disappearances, weird sounds, apparitions and chilling tales.

Trains are still active at this location, so visitors should not enter the tunnel at this portal. 

Close-by is the unmarked Cascade Brook trailhead, just to the right of the tunnel, over the stone wall, beyond the entrance.

1/2 mile trail to the base of the waterfall, steep & narrow, moderate.

239 River Road, Florida, Mass.

10. West Branch Chapel Cemetery at October Mountain State Forest

Hidden deep in the woods of October Mountain State Forest is an abandoned cemetery. Somewhere in this reclaimed wilderness, lies Anna Pease, age 10. Anna died on January 22, 1829 and though her short life remains a mystery. Her presence as a ghost is infamous. Reports of a ghostly spectre seen wearing a white dress haunt the area, as well as strange humming noises.

The surrounding lands were once the retreat of William C. Whitney, the secretary of the navy under President Grover Cleveland. Here he owned 14,000 acres, making him the largest landowner in Massachusetts. Whitney built a massive game reserve in the October Mountain woods and since its abandonment, it too has become a hot spot of paranormal activity. Vampire bats, “horned devils” and glowing-eyed beasts are among the ghastly sights. Some claim they’re the descendants of Whitney’s game escapees roaming the woods, while others say Whitney himself still haunts the ruins of his old estate, forever hunting the forests for big game.

Drive to the reservoir on top of the mountain and park in the parking lot. The path to the cemetery is across the road. The trail will take you by an old stone foundation of an old home and the cemetery is a little way up on the right.

Unmarked trails. Use at your own risk.

October Mountain, West Branch Road, Washington, Mass

11. Sinister Springside Park

According to local journalist and master folklorist Joe Durwin, Pittsfield’s Springside Park has it share of the macabre.

“I grew up around Springside Park, so there were a lot of stories about Springside. There was a lot of stuff we talked about as kids. That park has a lot of lore, some of it sweet, some of it kind of scary.”

In the 1970’s and 80’s, multiple killings of animals in the park’s petting zoo were reported in the Berkshire Eagle. Among the more horrible incidents, were those of 1972, when a baby pig was stabbed to death, a goat crippled and a peacock’s feathers were pulled out. Later chalked up to “vandalism” in the 1980’s, these disturbing acts and others ultimately closed the Springside Children’s Zoo.   

In These Mysterious Hills, Durwin’s extensive historical blog of the Berkshires, he tells of another gruesome crime that occurred at Springside in the 19th century. 

“…few recall that, in the late 19th century, the dismembered torso of a human corpse was found not far from the Springside House, then called the Elmhurst House. The body was never identified and the killer never apprehended, but the crime may have left some lasting residue on the area. A local woman of exceedingly solid character shared with me the story of how, some decades ago, she and her boyfriend were walking down the circular drive of Springside House when what they then thought to be an uprooted tree stump suddenly began lumbering toward them. Later, when they heard of the murder, they speculated that it might actually have been the hands and feet of the unfortunate victim. And reports have continued to trickle in over the years of a horrific floating head, which has been seen by many residents of the west side of North Street, across the street from the Springside house. “The Head,” as it is often called, is usually described as a ghastly skull with bits of decomposed skin still clinging to it. It is interesting to note that these houses stand on land that was once a landfill.”

Springside Park has numerous hiking trails and rotting relics of its past. Ask a local for the location of the abandoned petting zoo. Explore at your own risk.

874 North Street, Pittsfield, Mass 

12. Ashintully's Egyptian Curse

Walk the grounds of the former 120-acre estate of Robb de Peyster Tytus. In 1910, this politician and Egyptologist built a white mansion that would come to be known as the “Marble Palace.”

Tytus didn’t enjoy his beautiful estate for long. Shortly after its completion, Tytus succumbed to tuberculosis at the age of 38. His death was the first in a series of misfortunes that led many to believe that the family was cursed. In 1928, his wife Grace died suddenly of a pulmonary embolism and 5 years later, their 28-year old daughter Mildred was killed in a car accident driving home from the Ashintully. An article written in 1951 discussed the dogging rumor that the family had incurred the wrath of Egypt’s dead kings by disturbing their sleep in the search for ancient relics. When the estate burned to the ground in 1952, those rumors stuck forever.

Easy trails through the mansion foundations and gardens.

Sodom Road, Tyringham, Mass

13. Bigfoot at Felton Pond in October Mountain State Forest

Bigfoot lives in the Berkshires!

Sightings of the burly biped date all the way back to 1765. One of those most significant sightings occurred in the late summer of 1983. Four friends were enjoying a cookout near Camp Eagle, an abandoned Boy Scout camp on the shore of Felton Pond, when suddenly the night was interrupted by a large rustling in the distant brush. Hoping that the noise was a nosy bear, they ignored it and went back to enjoying their night. After a couple hours passed by and the noises had not let up, two members of the party went out to investigate. What they saw less than 100 yard away was definitely not just a curious bear. 

“It stood on two legs, silhouetted on the trail in the moonlight, and it was huge.” Durant told the Berkshire Eagle a few days later, “I don’t scare easily, but it scared me.” 

Though this is perhaps the most famous record of a “Bigfoot sighting” on October Mountain, it is certainly not the only one. The mountain has been the focus of paranormal investigations, spooky documentaries, and eyebrow-raising stories of weird and wild creatures. See the above info on the West Branch Chapel Cemetery for more information.

Various trails, including Felton Pond Connector Trail and Gorge Trail, Intermediate to Difficult

October Mountain State Forest. 317 Woodland Road, Lee, Mass

Know any other spooky trails? Drop them in the comments!