Legends of America’s Past: Tales & Tombstones Haunted Trolley Ride with Kids, in Salem, Massachusetts

Salem, Massachusetts didn’t prove to be quite what we expected. During our trip to Boston, we carved out a day to spend touring the most iconic Halloween destination in America. Rather than festive Halloween celebrations, however, we found little more than a torture chamber of silliness. While we infinitely enjoyed learning about the history of Salem, and touring the Harbor Sweets Chocolate Factory, we also suffered through the Witch Dungeon Museum and then Frankenstein’s Castle. By 3:30p we were ready to head out of town, but we had to stick around for four more hours before our pre-paid Tales & Tombstones Trolley tour! We were reticent to waste any more money on “museums and attractions”, so we found it preferable to camp out in the Visitor’s Center. We took a short nap in the auditorium during the video of shoes and textiles, walked around town for the upteenth time, had dinner and dessert, and finally made our way to our designated boarding spot. This was totally worth the wait! The Tales & Tombstones Trolley Tour renewed our interest in the history of Salem, and what this historic city has to offer!

► Ranking: #cleandiaper

Tales & Tombstones Salem Trolley Tour
8 Central St, Salem, MA 01970
Phone: 978-744-5469
Prices: Adults $20.00 | Children 6-14 $10.00

Our 90 minute tour of Salem traveling through eight miles of the city, covers all the iconic institutions. We heard ghost stories at every location and learned more about the sordid past and history of Salem, Massachusetts. We cannot recommend this tour enough! Though the trolley offers daily tours of Salem year round, the Tales & Tombstones version is only available during the Halloween season.

Similar to our Duck Tour in Boston, the narrator for the tour sits at the front of the trolley facing guests, answering questions and weaving tales. We enjoyed our tour with a group of fun older women who were hooting and hollering the whole ride! We went slow enough through town to get a good look at each of the asylum’s, even pulling over to stop when able. Many of the stories we heard you’ll find littered throughout this blog as they correspond to the attractions we visited; other’s we’ll keep a mystery. One of our favorites include what happened at the original Rockafella’s Restaurant.

Before it was a restaurant, this old building was originally a residence. The married woman who resided here had an illicit affair with a ship’s captain. When her two lovers found out about her cheating ways, they acted out the ultimate crime of passion. In order to hide their crime, they built a false wall in the home and hid her body behind it, sealing it up with bricks and thick mortar. When the building underwent reconstruction hundreds of years later, the false wall was found, with her bones and scratch marks covering the inside wall.

The Tales & Tombstones tour also took us around the wharf and by a older home, painted a beautiful shade of blue. Originally, this home started off as a small one story and then, years later, the owner decided to build a second story using the shell of an old ship. Guests who visited the home would often remark how cold the upstairs was in comparison to the rest of the house, and if any time was spent upstairs a voice could be heard distinctly yelling the words, “Get Out! Get Out!” Upon investigation it was discovered the ship used to build the second floor of the home belonged to a captain who was murdered in his cabin! Guess what his final words to his murderer were?

Another one of the most interesting things we learned on the Tales & Tombstones tour is the literal imagining of how people in Salem have succumbed to being scared to death. The city of Salem is full of underground passageways originally built to house vents for heating the buildings above ground. These passageways were also used by smuggler’s throughout Salem’s past (reminds me of the Portland Underground Shanghai Tunnels). More recently, they have been used to transport jewelry and goods nightly from the storefronts safely away from robbers and thieves. As you can imagine, the passageways are also full of ghosts, and other bumps and sounds in the night. Several residents traveling in these tunnels have died from sheer fright!

► For Kids: Many of the stories on the Tales & Tombstones Trolley Ride have to do with dying and death, so beware. Our children, aged 6 ½, were a little spooked by a story of a man being overpowered by a ghost, but nothing a playful answering of questions couldn’t fix.  Dress warm, and/or bring a blanket! 

This was, hands down, the coolest thing we did in Salem! It made us want to come back and experience more of what this historic little town has to offer. From the maritime records, to the layout of the city itself, to the insanely beautiful homes, and of course, the ghost stories, this city definitely has more to offer than the foolishness in Witch Village.

► Nap-Time Version: Tales & Tombstones is one of the best Halloween events in Salem, Massachusetts and elsewhere! A great activity for the whole family, and a fun way to learn about the story of one of America’s oldest cities.

Check out our tour of Harbor Sweets, a handmade confectionery in Old Town, Old Burying Point Cemetery, and Red’s Sandwich Shop (coming soon).