Halloween in Boston: When the City Gets a Little Spooky

There are cities that celebrate Halloween. And then there’s Boston. Maybe it’s the centuries-old graveyards. Maybe it’s the narrow streets that seem made for wandering after dark. Maybe it’s the brick townhouses glowing behind carved pumpkins, the fallen leaves collecting along the sidewalks, or the fact that in a city this old, almost every neighborhood seems to have a ghost story.

Whatever the reason, Halloween feels perfectly at home in Boston.

By October, the summer crowds have thinned, New England foliage has turned shades of crimson, orange and gold, and there’s a chill in the evening air that makes you reach for a sweater. Then the pumpkins appear. Brownstone stoops are transformed with jack-o’-lanterns, skeletons, cobwebs and the occasional resident ghost. Beacon Hill becomes particularly photogenic after sunset, while Back Bay’s Victorian architecture provides a suitably dramatic backdrop for the season.

And Boston being Boston, some of the spooky stuff is actually true.

Start With Boston’s Darker Side

You don’t have to look very far for a little macabre history. Boston has 16 historic burying grounds, several dating back to the 1600s. Three, Granary, King’s Chapel and Copp’s Hill, sit along the Freedom Trail.

Granary Burying Ground was established in 1660 and is believed to contain the remains of more than 5,000 Bostonians, despite having only about 2,300 grave markers. Paul Revere, Samuel Adams, John Hancock and victims of the Boston Massacre are among those buried here. Look closely at some of the old slate gravestones and you’ll see winged skulls; representations of the Grim Reaper and other imagery associated with death and the afterlife. Suddenly those plastic skeletons decorating the neighborhood don’t seem quite so scary.

See the Freedom Trail by Lantern Light

You can walk Boston’s famous red line during the day. But around Halloween, we prefer it after dark. The Freedom Trail Foundation’s seasonal Lantern Tours explore the more sinister side of Boston history, with tales involving murders, pirates, accused witches, executions and other events that rarely make it onto the standard sightseeing itinerary.

Costumed guides lead visitors through historic Boston by lantern light, including stories connected to Boston Common, Granary Burying Ground, King’s Chapel Burying Ground, the Boston Massacre site and the location of the old jail. No haunted-house special effects required. Boston has had nearly four centuries to come up with its own material.

Go Looking for Boston’s Best Halloween Stoops

One of our favorite Halloween activities doesn't require a ticket at all. Just go for a walk. Boston's historic neighborhoods seem almost designed for Halloween decorating. Pumpkins line front steps. Skeletons appear in windows. Spiderwebs stretch across iron railings. Wreaths turn black and orange, and otherwise dignified old townhouses suddenly acquire witches, ghosts and creatures climbing their façades.

Beacon Hill is especially wonderful for an early-evening Halloween stroll. Wander some of the smaller streets off Charles Street and see what you discover. Then head back toward Back Bay, where the grand brownstones take on a completely different personality after dark.

Halloween sightseeing rule: look at the stoops, but don't forget to look up. Some of Boston's best architectural details are above eye level.

Visit a Cemetery—While the Sun Is Still Up

For a quieter encounter with Boston's past, visit one of its historic burying grounds during the daytime. Copp's Hill Burying Ground in the North End dates to 1659 and contains the graves of generations of Bostonians, including Puritan ministers Cotton and Increase Mather, who were closely associated with the era of the Salem witch trials.

Or explore Granary Burying Ground downtown before continuing along the Freedom Trail. These aren't Halloween attractions created for October. They're pieces of the actual city, which is exactly what makes them so fascinating. Please remember that they are historic burial grounds, so explore respectfully.

Make Halloween an Excuse to Wander

Not everything about Halloween weekend needs to involve ghosts. October is simply a wonderful time to explore Boston.

Walk through the Public Garden with leaves crunching beneath your feet. Continue across Boston Common. Duck into a café when the temperature drops. Wander through Beacon Hill, cross over to the North End, or follow part of the 2.5-mile Freedom Trail connecting 16 historic sites.

October also brings a full calendar of seasonal events throughout Greater Boston, making it worth checking what's happening while you're here. And when darkness arrives early? That's when Boston starts looking particularly good.

Want More Halloween? Salem Is Waiting.

Of course, there is a certain Massachusetts town approximately 16 miles north of Boston that becomes rather famous this time of year.

Salem.

If Halloween is the reason for your trip, consider making it a day excursion while keeping Boston as your home base. Explore Salem's witch-trial history and October festivities, then return to Boston for dinner, drinks and considerably fewer witches per square mile. October is one of Salem's busiest periods, so transportation and attractions should be planned well in advance.

Or Simply Have a Halloween Night on Newbury Street

You don't actually have to go anywhere. Spend the afternoon shopping Newbury Street. Take a walk through the neighborhood as the pumpkins begin to glow. Find somewhere cozy for dinner or a glass of wine. Then come home to Newbury Guest House.

Our three connected Victorian residences have been part of Newbury Street since the late 1800s, and we've kept many of the details that give them their character—from bay windows and decorative fireplaces to original architectural touches. Yes, even a few squeaky stairs. Are they simply old stairs?

We're sticking with that explanation.

Stay in the Middle of Boston’s Halloween Magic

Halloween in Boston isn't really about one attraction or one night. It's the atmosphere.

It's a jack-o'-lantern flickering on the steps of a brownstone. A centuries-old gravestone beneath autumn leaves. A lantern disappearing around a corner. The smell of coffee on a cold morning. Brick sidewalks covered in gold and red. And that wonderful feeling that Boston's past is never very far away.

At Newbury Guest House, you're right in the heart of Back Bay, with Boston Common, the Public Garden, Beacon Hill and many of the city's historic neighborhoods ready to explore. So pack a sweater. Bring comfortable shoes. And perhaps leave a little room in your suitcase for a costume.

Boston is waiting.

And this October, it might just be waiting after dark.