Dark Hollows Haunted Trail
“With every shriek and stumble, we welcomed new survivors to the club of those who had escaped the Dark Hollows Haunted Trail.”
- J. Coursey Willis
It was the last October weekend before Halloween, 1996. A chilly Saturday night under the bright glow of a Hunter’s full moon. Distant screams and eerie sounds echoed through the air. They mingled with the nervous chatter of a few hundred people packed into the parking lot of Terrapin Park, waiting their turn to enter Kent Island’s fastest-growing haunted attraction.
My best friend and I sat in a damp wheat field, the mist cooling our faces. Suddenly, a chainsaw’s roar ripped through the night, followed by terrified cries. The next group was funneling down the grassy path toward us—the last stop before the long, dark exit. Adrenaline replaced the cold in our bodies as we braced for them. With every shriek and stumble, we welcomed new survivors to the club of those who had escaped the Dark Hollows Haunted Trail.
I’ve had a forever fascination with the macabre—things that go bump in the night. At ten, I built Halloween displays in my parents’ front yard on Cox Neck that sent sweet old ladies into fits. Cemeteries perpetually draw me in, the stories etched into the stones calling out to be known. October is my favorite month, and The Nightmare Before Christmas has been my creative compass for as long as I can remember. Growing up on historic Kent Island, steeped in lore and legend, I naturally found myself pulled into the world of haunted attractions.
The idea for Dark Hollows Haunted Trail was conjured in 1993 by a group of locals. County Parks & Recreation, WCEI radio station, the Kent Island Jaycees, and the Modern Woodmen of America sponsored the event. Though the annual ritual only lasted six years, the memories it created endure.
Terrapin Nature Park, with its twisting wooded trails and open fields along the Chesapeake Bay, made the perfect setting. Advertisements for Dark Hollows began running in local papers by late September, and the Bay Times captured its essence, calling it “the playground for Kent Island’s most enchanted spirits.”
Each year carried a theme, beginning with the legend of Ana, a beautiful girl with wheat-colored hair who had vanished mysteriously. A fortune teller greeted guests at the trail’s entrance, preparing them for their search. For $2 a head, the search party entered at their own risk, winding through the dark woods, chasing the hope of finding Ana.
The event was a smashing success. Between 7:00 and 10:00, 600 guests braved the trail, raising $1,200 for local causes. By the following year, the Kent Island Volunteer Fire Department (KIVFD) joined forces with Parks & Recreation to organize the event. The partnership gave the fire department much-needed funds to support their work on the growing island.
1994 was another hit, and with experience under their belts, the crew doubled down in 1995, offering two nights of scares and bumping admission to four dollars. The haunted attraction’s spell spread like wildfire, and by 1996, it stretched into a three-night event. That year stands out as my favorite—until then, I’d only walked the trail as a spectator. But thanks to a very special Halloweenswoman, I finally became part of the show.
I met Mrs. Sylvia Taylor in 1992 through my best friend, Joe Q. He and I spent endless hours on his street, Cheslou, watching old horror films and reading Scary Stories to Tell in the Dark. Sylvia lived just down the road, and her Halloween displays were legendary. People drove from miles around to see her work—guillotines, gallows, graveyards, even alien spaceships, all set to theatrical soundscapes. It was Sylvia who taught me the art of the scare.
Joe and I became live props in her displays, sitting still as stone until unsuspecting spectators stepped out of their cars for a closer look. Then we’d leap into action, earning gasps and terrified screams. Sylvia’s creativity opened a new world for me—a world where horror and art met. From then on, my dad and I spent every September building creatures, using cinder-blocked wooden crosses as skeletons. We’d dress them in attic clothes, attach gloves and boots, and fit Halloween masks over stuffed grocery bags. By October, our yard was filled with an army of horrors, drawing the attention of passersby and local papers.
By 1995, Sylvia was ready to pass the torch. After a decade of elaborate displays, she donated her collection to Dark Hollows and recommended that Joe and I join the crew. In 1996, we became part of the magic.
On the first night of Dark Hollows Haunted Trail IV, our parents dropped us off at Terrapin Park, where we earned the nickname “The Boys.” We rotated roles along the trail, but I remember Joe best as a crazed prisoner who escaped through the bars of a cage, chasing victims through the fog. That year, a dollar bought guests a new hayride experience, where Jason Voorhees—played by beloved firefighter Wally Alden—burst from a duck blind with a roaring chainsaw, sending crowds fleeing.
Every year brought new thrills. One friend, Nathan, played a soldier chasing aliens through the woods. Another year, a dump truck (or maybe it was a fire truck) lay hidden in the brush, its headlights and horns suddenly blasting as groups approached. The volunteers pulled out all the stops—electric chairs, psychotic clowns, and victims trapped in giant spider webs.
At its peak, Dark Hollows drew 1,500 visitors to its mysterious paths and raised nearly $5,000 annually for the fire department. The trail became known for its intensity. Children under 12 had to be accompanied by adults, and strobe light warnings were posted at the entrance. This was not a haunt for the faint of heart.
But as with all things, Dark Hollows came to an end. In 1999, the county reclassified Terrapin Park as a protected nature area, forcing the event to relocate behind the library. The smaller, less eerie setting changed the dynamic, and heavy rains that year canceled the trail altogether. With $5,000 in lost revenue, the KIVFD’s general fund took a hit, and the beloved Dark Hollows Haunted Trail, along with its well-worn props, was laid to rest.
I cherish those October nights—feeling connected to something bigger than myself, both terrifying and being terrified. The memories linger with the scent of fallen leaves on an autumn breeze, taking me back to that chilly night in 1996, waiting in the wheat field for our next victims.
Halloween on Kent Island isn’t what it used to be, but I still hold out hope. The island needs its haunted trail back, and in 2021, with all my energy, I set out to reanimate it with the Possession of Kent Asylum. We returned in 2022 with HYSTERIA—and we’re just getting started.
PS: If you have photos from the original Dark Hollows, I’d love to see them. Please email them to [email protected] or mail them to:
Historic Kent Island, Inc.
PO Box 444Stevensville, MD 21666
Resources:
1993 I - Admission $2 (Oct 29 Fri 7-10pm Rain Date Oct 30 Sat 7-10pm)
1994 II - Admission $2 (Oct 28 Fri 7-10pm)
1995 III - Admission $4 (Oct 27-28 Fri-Sat 7-10pm)
1996 IV - Admission $3 (Oct 25-27 Fri-Sun 7-10pm)
1997 V - Admission $4 (Oct 23-25 Thu 7-10pm Fri-Sat 7-11pm)
1998 VI - Admission $4 (Oct 21-24 Wed-Thu 7-10pm Fri-Sat 7-11pm)
1999 VII - Admission $5 (Oct 28-30 Thu-Fri 7-10pm Sat 7-11pm)
9/22/1993 - QA Record Observer - Parks & Recreation Announcements
11/3/1993 - KI Bay Times - Haunted Trails Draws Nearly 600
10/24/1994 - KI Bay Times - Halloween Parties, Costume Contests Planned
10/25/1995 - KI Bay Times - Bay Calendar Haunted Trail III
10/23/1996 - KI By Times - Halloween Activities Haunted Trail
10/30/1996 - KI Bay Times - A Haunting We Will Go
10/30/1996 - KI Bay Times - A Haunting Good Job For A Good Cause
10/8/1997 - KI Bay Times - Bay Calendar Dark Hollows Haunted Trail 5
10/22/1997 - KI Bay Times - Scream For A Good Cause
10/21/1998 - KI Bay Times - Meet Scary Characters Like Jason...
10/28/1998 - KI Bay Times - Haunted Trail
10/22/1999 - QA Record Observer - Halloween Events & Activities Scheduled
