Spend a Day Investigating Haunted Places in Boston

Just in time for Halloween, one writer plans her best guide to the creepiest (and fun!) adventures in town

Nothing gets me pumped for Halloween like a good ghost hunt and some macabre sightseeing. In an ancient New World city like Boston that’s not hard to do.

Hangings, privateering, massacres, wars and treachery—it’s all part of our story. Look hard enough, and you’ll find grisly details along The Freedom Trail and at the Waterfront, among the Italian restaurants of the North End and tucked into the collections of our libraries and museums. I eschew costumes and instead dedicate a day to creeping myself out. Haunted hotels and restaurants, centuries-old cemeteries, even a book bound in human skin—all ready to cause delicious danger to your mental constitution.

Start off this macabre journey with a visit to Boston Athenaeum. Boston’s oldest independent library is an absolutely stunning place to visit on any day, with its architecture, fine art and ornate galleries.

But what will stun you on this visit is the 1837 memoir “A Narrative of the Life of James Allen: Alias George Walton, Alias Jonas Pierce, Alias James H. York, Alias Burley Grove, the Highwayman: Being his Death-Bed Confession, to the Warden of the Massachusetts State Prison.” The titular highwayman and thief had his life story recorded and then bound in his own skin post-mortem before gifting the whole package to one of his victims. Today, visitors can make an appointment to see the rare book. (Read it online, here.) 
10 ½ Beacon St., Boston, MA, 617.227.0270

See James Allen's human skin-bound memoir at Boston Athenaeum (©Boston Athenaeum)

You won’t need to go far for your next stop: Granary Burying Ground sits in the Athenaeum’s back yard. Although this hallowed site was founded as early as 1660, it only earns the designation as Boston’s third-oldest cemetery.

Slate headstones lend a creepy feel, etched with haunting Puritan images like the soul effigy, the willow and urn, and Father Time. Famous folks interred here include the victims of the Boston Massacre, Samuel Adams, John Hancock, and perhaps most notably, Paul Revere. Fun fact: Estimates have the total number of bodies buried at Granary at greater than 5,000, even though there are only 2,300 headstones.
Tremont Street at Park Street, Boston, MA, 617.635.4505

Granary Burying Ground (©George Burba/istockphoto)

Across Tremont Street, King’s Chapel plays host to a little-known gem of an experience that becomes particularly relevant during this season.

The Bells and Bones Tour explores the church’s dank 200-year-old cellar crypt where 21 tombs contain the remains of wealthy Revolutionary-era Tories. No particular hauntings to note, but the dim light and creaking of floorboards overhead gives the experience an eerie flourish.
58 Tremont St., Boston, MA, 617.523.1749

Stop for a mid-afternoon coffee break at nearby Ogawa Coffee. The first international location for the legendary Japanese coffee roaster, this place offers a taste of its homeland's coffee culture with specialty beans and a bold level of caffeine. But why has it made this particular list of spooky things to do? During the month of October, ghosts and jack-o'-lanterns haunt the milk foam of all lattes served (by request Oct. 1-28; automatically Oct. 29-31).
10 Milk St., Boston, MA, 617.780.7139

Halloween latte art at Ogawa Coffee (Courtesy Ogawa Coffee)

Here's a quick history lesson: Mary Dyer, an English woman who emigrated to Massachusetts in 1635, was imprisoned, banished and, finally, hanged on Boston Common in 1660 because of her Quaker religious beliefs, considered heretical by Puritans and the Anglican church.

Today, a bronze sculpture of Dyer by artist Sylvia Shaw Judson (Beacon Street at the State House) commemorates the freedom fighter and overlooks the Common. After checking it out, walk through the park, which was once home to the Great Elm tree from which Dyer was hanged—it fell to weather in 1876 and was removed. For centuries, a ghostly apparition appears from time to time—see if you can catch her at it.
24 Beacon St., Boston, MA

You do get to pause for a meal, but it doesn't mean you get a pause in our day of frightful fun. Have a haunting with your dinner at The Brahmin, a Back Bay restaurant with a nightclub-style vibe. Menu features sharing plates including asparagus-parmesan fries, spicy panko-crusted rock shrimp and duck confit sliders.

Supernatural activity spiked when owner Russ deMariano and his team were renovating the space—once a horse stable in the early 1900s—before opening a few years ago. He says, "It happened a lot while we were under construction. We always heard loud crashing noises, like glasses breaking." deMariano's mother was the first to witness a man in an old-style gray suit sitting in the kitchen. Today, deMariano, his partner and many of his staff have also seen it and heard it. "Lights will go out and then go back on. There are weird flickers a lot of the time," he says. "It happens a lot."
33 Stanhope St., Boston, MA, 617.723.3131

Walk off dinner on a Ghosts & Gravestones Boston Frightseeing Tour. This tour by foot and trolley is a delightfully campy, theatrical adventure and perfect buffer to the anticipation of spending the night in a haunted hotel. No, really. But we'll get to that. Fully ghouled-out black trolleys with grave-digger guides take passengers around town after dark to notorious sites (as in where the Boston Strangler attacked one of his victims) and a number of the city's cemeteries, all the while regaling riders with purportedly true ghost tales.
200 Atlantic Ave., Boston, MA, 617.269.3626

Ghosts & Gravestones players and guides (©Michael Blanchard)

To end your day, have a wander around the historic Omni Parker House Hotel, or better yet, book a room and spend the night. This absolute stunner celebrates its 160th anniversary in 2015 and can be tied to dozens of famous characters, from Ho Chi Minh who worked in its kitchen, to Charles Dickens who was a habitual guest of the hotel's third floor.

The Parker House is one of Boston's most magnificent places to stay, and hospitality has always been a priority here, especially for founder Harvey Parker. Speaking of whom... He reportedly still checks in from time to time to make sure things are running smoothly. Guests of the 10th floor have seen his hazy likeness roaming the halls; one even woke up to him standing, smiling at the foot of her bed. But Parker isn't responsible for all ghostly encounters here: The elevator is known to travel back and forth to the third floor without being called, and a rocking chair can sometimes be heard rocking late into the night.
60 School St., Boston, MA, 617.227.8600