The Perfect Hike for Spooky Storytelling

September 29, 2022 / Good to Know, Outdoor Adventures, Things to Do & See

The Perfect Hike for Spooky Storytelling | Gloucester Writers Center

In the woods of West Gloucester, find otherworldly landscapes to share your spookiest tales. 

A sea serpent. A mysterious light. Two ghostly lovers, forever in their surfside castle. Whether simply unusual or bloodcurdlingly frightening, stories of supernatural phenomena and encounters have been part of the landscape of Cape Ann for centuries. With fall here, it’s time to lace up our boots and hike West Gloucester’s dense and seemingly endless public parks to find the perfect, spooky place for late afternoon scary stories. 


To reach our favorite spot, we head to the forested area around Dykes Pond and Lily Pond. (Follow Route 127 from Downtown Gloucester, over the Cut Bridge, and turn right onto Essex Avenue, Route 133. Continue past the West Gloucester MBTA station until you reach Laurel Street, and then wind your way slowly through the woods on Laurel until you find a small parking lot on the right. You’ll know you’re there if you see a dirt road and yellow gate leading into the woods.)


Once you pass the gate, follow the road into the forest, with Lily Pond on your left. (Listen for ghostly train whistles as the Commuter Rail snakes its path in the distance.) From this access road, we recommend two different routes. 


For the more experienced hiker, continue on the road until you find a trail on the left, its entrance marked by an opening in two tall rocks. We recommend taking a walking stick, as the fall leaves can make this pathway slick! Follow the narrow trail down into the wetland area, cross the narrow wooden bridge, and then—with the help of your stick or a hand on a tree trunk—continue to follow climb the path up and deeper into the woods. A few moments later, you’ll emerge quite suddenly into an abandoned camp site with an imposing, stone hearth. Golden light falls through the quivering branches, and the wind moans. Distant cracking of sticks echoes in the woods, and a crow screams overhead. Perhaps you’re not totally alone. Gather around and begin sharing your tales. 


For a less strenuous walk, simply follow the original access road to its end. As the trees thin out, look up and find the dry, concrete spillway for Dyke’s Pond, one of Gloucester’s reservoirs, in the distance. Continue into the clearing, where dramatic slopes of brown and amber grass meet rock and concrete now doused on all sides with graffiti, as above a stark concrete structure looms from the reservoir over the eerie landscape. The October sun casts an orange pall on this weird vista. Watch the big, empty sky…for UFOs.


Looking for stories to tell? Keep it local with haunting tales of Gloucester’s past. Below, we sketch a few to whet your appetite. Learn more about the area’s ghosts and ghouls at Hammond Castle Museum, just down the road in the Magnolia neighborhood. An actual castle, once home and laboratory of inventor John Hays Hammond, Jr., father of the remote control, the site was built from salvaged antique architectural elements. Sitting on a cliff overlooking the ocean, it is filled with Hammond’s collection of ancient and medieval artifacts. It’s an inherently spooky place, made even more so through a slate of great supernatural-themed programs in October. Plus, it doesn’t hurt that Hammond Castle remains one of Gloucester’s most haunted places—it’s said the ghosts of Hammond and his wife continue to appear unannounced.



Beginning in the 17th century, reports of a giant serpent plying the waves off Gloucester began to circulate around town and appear in the press. Reports describe a sixty-foot long beast, with the head of a turtle and a spike on its tale. In the early 19th century, sightings became so fevered and frequent that scientists from Boston arrived to investigate. Then one day, an unrecognizable black creature washed up on the shore—the serpent’s offspring? Sightings continue today. 



In July 1692, a shadowy group of people emerged from the swamps and cornfields surrounding Gloucester. Speaking an unknown language, they approached the town garrison; bullets had no effect on them. For weeks, these spectral beings continued to haunt the town at night—some believed they were real, claiming later to have pull the ghosts’ own bullets from trees where they’d been lodged. Others saw them as supernatural beings sent by the devil. 



While nearby Salem holds the title “Witch City,” Gloucester has its fair share of witch lore. (In truth, many of Gloucester’s accused witches were outcasts living on the edge of society, making them easy targets for superstitious city folk.) Most stories focus on the women of Dogtown, an abandoned early settlement at the heart of the city. One tells of Peg Wasson, flying over the town on a broomstick or in the form of a crow. Another tells of Tammy Younger, who allegedly cast spells on oxen. 



On March 29, 2021 reports of a glowing sphere hovering over Gloucester harbor began to circulate. While not well-known as a hotspot for extraterrestrial contact, the city has seen its fair share of UAP (unidentified aerial phenomenon) sightings over the years. With the Pentagon now admitting that we really cannot explain everything we see in the sky, we recommend settling in and looking up: according to one recent study, Gloucester is the 14th most supernatural city in Massachusetts, with eight ghost and twenty-three UFO sightings last year. 


Click here for more spooky fall activities in Gloucester.