As some of the earliest settlements in Massachusetts, Gloucester and the surrounding towns have a lot of history. Gloucester has long been a fishing village; many people from the start have lost their lives to both the sea and to pirates. Nearby you can find the infamous Salem, known for the witch trials in the 1690s.
Because of all of this history and these really unfortunate deaths, there are a lot of cool places to checkout in the area. Especially in the weeks leading up to Halloween. And although I tend to stay away from all things scary, this year I was very curious about how many places around me are supposedly haunted.
Salem steals the spotlight from September 30th through November 1st. The witch museums and just the city in general attract thousands of tourists during this time and because of this I try to avoid the area.
Like I said, I avoid all things scary, and I mean I will literally sleep with my television on Disney channel to avoid previews for a scary movie. The one thing that is drawing me to Salem this October is nothing haunted. In the middle of town is Wynott’s Wands, a witch shop like the many others around it but featuring wands from my favorite series- Harry Potter.
Right around the corner from Wynott’s Wands is the Hawthorne Hotel. Constructed in 1925, the hotel has since had over one million guests including Bill Clinton, Robert De Niro, and Jennifer Lawrence.
The hotel is also reportedly haunted on the sixth floor as well as room number 325, where many people have claimed to witness weird happenings over the years. The Hawthorne Hotel is still a functioning hotel, book a room here if you are brave enough.
From Salem you can take route 127 North towards Gloucester. You will pass through the town of Beverly before passing Endicott College. There are several buildings on Endicott’s campus that have had multiple reports of hauntings.
In my opinion, Winthrop Hall has the most interesting haunted tale. The hall is now a residence for students but was previously a waterfront mansion and home to a woman widowed at the hands of the sea and still waiting for her husband to return.
Continue following route 127 past Manchester-by-the-Sea and you end up in Magnolia, a small village within Gloucester and home of Hammond’s Castle.
John Hayes Hammond, Jr. was an inventor who is known as the Father of Remote Control. While he was alive, Hammond would remote operate his boat in the harbor from the confines of his castle to scare the people of Gloucester with this “ghost ship.”
Hammond was also, reportedly, a believer of reincarnation and a cat lover. Visitors to the castle have reported sightings of stray cats and the smell of cat urine. You can visit the castle year round but before Halloween the castle is transformed into a haunted house.
Dogtown is one of the most eerie places in Gloucester. It started as an inland civilization for fishing families who needed distance from the pirates that terrorized the coastline. As the settlement was abandoned or inhabitants died, their dogs were left behind, became feral and gave the area its current name.
Since this time, the area, deep in the woods, has become home for homeless and growing up I was advised to stay away from it. Many people have died in these woods, the most recent being about 30 years ago when Anne Natti was murdered here.
The history of Dogtown as well as the story of this murder was unraveled by Elyssa East in her book “Dogtown: Death and Enchantment in a New England Ghost Town” and is a book I recommend to anyone unable to take the trip themself.
It is not a place I would venture through alone or without a map, but the hiking trail through Dogtown is still maintained and accessible. If you dare to enter these woods keep your eyes open for the boulders etched with motivational phrases by Roger Babson.
While I enjoy learning about these places, reading is as close as I will get to anything that is supposedly haunted. Stay safe and happy hauntings.