Person using a knife to carve a face design into a pumpkin in preparation for Halloween, pumpkin carving workshop
Photograph: Shutterstock | |
Photograph: Shutterstock | |

The 13 best ways to celebrate Halloween in Boston for spooky fun

Spooky season has descended. Here’s how to get your thrills and chills in and around Boston this October.

Jacqueline Cain
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As one of the oldest cities in the country—and one with the prettiest fall foliage—Boston is a prime place to visit in October. The region has historic haunts you can't miss, whether it’s one of our creepy old graveyards or a verifiably spooky site with a story that would put your favorite true-crime podcast to shame. But it's not all about the fear factor around here, with family-friendly fun floating around, too.

If you want to celebrate the season without waiting for all the annual Halloween parties and events to happen, here's how to get your tricks and treats out and celebrate Halloween in Boston all October long.

RECOMMENDED: The best things to do in Boston

Time Out Market Boston

Whether your vibe is fun and family-friendly or suggestive of scary, Time Out Market Boston has a festive event for you. The Fenway food hall is going all out in October with on-theme drag brunch and pop-up markets, a pumpkin carving class, Ciderfest and more! Save the date for the market's annual Halloween Bash on Saturday, Oct. 26, at 9pm; it'll put a spell on you, for sure. All paired with seasonal cocktails, beer and food from the market's many local options, Time Out Market is your cozy-season headquarters.

What to do on Halloween in Boston

  • Things to do

Halloween’s first order of business is to find yourself the perfect pumpkin for your stoop. Skip the puny grocery-store gourds and opt for one from an awesome family-run farm near the city where you can pick your own from a patch surrounded by idyllic farmland—and maybe even catch a hayride. Your options are plentiful—from the dreamy Lookout Farm in South Natick to the Boston Hill Farm in North Andover, where you can make a whole day of your excursion with a petting zoo, live music (on weekends) and a fresh farm stand doling out delectable autumnal treats. Apple cider donuts, anyone?

  • Shopping
  • Thrift stores
  • Kendall Sq
  • price 1 of 4

The next order of business? Where to find a costume in Boston! We’ve always been a fan of the Garment District during Halloween, which has everything you can think of for the perfect season’s getup—witches, ghouls, monsters, all the “sexy versions” of things and masks out the wazoo.L ooking for budget-friendly options? Head to the thrift section for some awesome retro finds, or simply Google other thrift stores near you. There’s nothing more satisfying than pulling together a costume from scratch from a discount bin!

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  • Things to do
  • Walks and tours
  • Waterfront
  • price 2 of 4

Explore the spookiest haunts in Boston on this 90-minute tour that focuses on tales of the Boston Strangler, the murders and executions on the Boston Common, and paranormal activity at the Omni Parker House. Most of the tour is aboard the trolley, but you’ll also walk through two of the oldest burial grounds in the city, and visit the site of a notorious grave-robbing scandal. The tour is available year-round, but Halloween is the best time to go (book tickets early), especially when you and your fellow guests get into the spirit in costume.

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  • Things to do

If you want to really embrace spooky season, Witch City is the place to be. Less than one hour from Boston, Salem is the absolute busiest in October, but if you plan ahead, there's no place like it. Leave your car at home: City officials advise visitors to take the commuter rail or a ferry boat (there's even a new route from Hingham this month!), or use a free satellite parking lot to shuttle into town. Once you're there, check out the Haunted Happenings Marketplace, visit the Salem Witch Trials Memorial, have a pint at Notch Brewery and a meal at a local restaurant and experience the best of Salem in October.

  • Attractions
  • Religious buildings and sites
  • North End
  • price 1 of 4

At the historic Old North Church, visitors can explore the main floor and bell chamber, but there’s something far creepier underfoot. The crypt below the historic church—reopened last year after a nine-month restoration project—offers frightening fun with vaults containing an estimated 1,100 bodies entombed between 1732 and 1860. On this dark and claustrophobic tour, you’ll learn about Anglican and Puritanical burial practices in colonial Boston.

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  • Things to do

We’ll happily put down our PSLs for a good jump scare this time of year. And luckily for us, there are plenty of spots throughout New England where sunlight can’t reach you and hair-raising Halloween thrills and chills await. Brand-new to Boston is a two-plus-acre Wicked Haunt Fest, the city's first full-scale Halloween experience. A little further afield, 10 other venues ramp up the terror with extreme special effects, elaborate costumes, gory makeup, eerie fog and spine-chilling sounds, as well. Most haunted houses run through October, but check the individual sites for schedules. And warning: these haunted houses, estates and terror factories aren’t for the faint of heart.

  • Hotels
  • Downtown
  • price 3 of 4

One of Boston's oldest and most historic hotels is believed to be haunted. Originally built in 1855 and rebuilt in 1927, the Omni Parker House is a stop on many ghost tours—but you can always grab a room to spend a whole night there. There have been reported sightings of a bearded gentleman dressed in colonial garb on the 9th and 10th floors, the elevators have been known to operate independently, and hotel staff have responded to complaints of eerie noises coming from otherwise unoccupied rooms.

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  • Things to do

Massachusetts can lay claim to some of the scariest ghost stories and hauntings ever recorded. From a former Revolutionary War hospital-turned-inn to a grisly family murder and the horrifying Salem Witch Trials, the shadows of our state’s dark past are never too far. Thrillseekers have plenty to explore in search of hair-raising spectral sightings and paranormal encounters. We’ve gathered 10 places rooted in the eeriest local lore for you to visit this fallInvestigate at will, but be warned: These are the homes of the undead; you’re merely a guest.

10. Go trick-or-treating on historic Beacon Hill

Whether you are a kid or a kid at heart, the most Boston of all Boston things to do on Halloween is to go trick-or-treating on Beacon Hill. The elaborate decor from Boston's toniest residents really make strolling their historic streets a treat for everyone. Enjoy the mayhem and the closed streets to enjoy plenty of elaborately decorated brownstones and maybe pick up some candy.

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