Skip to content

Home Boston Real Estate Insights Boston Activities

Top 5 Halloween Activities in Boston

5 minute read
Halloween events in Boston

‘Tis the season to be spooky. While Greater Boston’s heavy-duty, intensely terrifying haunted houses are located a fair bit out of town, there’s plenty of good, spooky fun to be had in and around Boston. If you’re in the mood for some seasonal festivities, read on… if you dare.

Get in the Halloween Spirit at Boston Bars & Nightclubs

Boston’s bar scene is second to none, and there’s plenty of spooky specials going around. From Halloween night costume parties to a variety of creepily-themed cocktails, there’s no shortage of seasonal fun to be had. Here’s a few of our favorites.

Official Boston Halloweekend Pub Crawl

Where: Faneuil Hall, 22-24 Clinton St. Boston, MA 02109
When: Saturday, October 26 at 5:00 PM to Friday, November 1 at 1:00 PM
What’s it going to cost? Between $10 and $16.66 for one day, $30 for a 3 day all-access pas, plus additional ticket service fees (between $2 and $3). And, of course, your drinks.
Anything else? 21+ only

While there’s nothing wrong with dressing up in costume and gorging on candy by yourself, let’s be real: Halloween is much more entertaining with a lively crowd. Far from an ordinary pub crawl, this Boston and event promises a roaring good time, making the term “favorite haunts” a bit more literal. Including Finn McCool’s, the Hard Rock, Mija Cantina, Howl at the Moon, and plenty more, if you’re looking to tear it up this season, Halloweekend has you covered.

Patio Pumpkin Carving @ Casa Caña

Where: Casa Caña, 1234 Soldiers Field Road Boston, MA 02135
When: 7:00 PM to 10:00 PM, Wednesday October 23
What’s it going to cost? $17
Anything else? 21+ only

It’s never a bad idea to head to the Nuevo Latino restaurant for Taco Tuesday, but Casa Caña has some spooky events in store this October. Pumpkin carving is a classic October tradition, and Casa Caña adds some Latin spice to the mix. For seventeen bucks, you get a pumpkin, a carving kit, one beer, and some toasted pumpkin seeds. Costumes are encouraged, and with games and their special autumn menu, it promises to be a fun way to spend a Wednesday night. Plus, they’re giving out a $50 gift card for the best pumpkin when all is said and done.

Catch a Show for Halloween in Boston

From guided tours to spooky illusions, Boston lights up the darkest of nights with world-class Halloween activities. While some of these mainstays entertain Boston year-round, Halloween brings out the spooky best in Boston’s tours, shows, and concerts for sure.

Halloween Night Cover Show @ O’Brien’s Pub

Where: O’Brien’s Pub, 3 Harvard Avenue, Allston, MA 02134
When: Doors at 8:00 PM, Show Starts at 9:00 PM, Thursday October 31
What’s it going to cost? $8
Anything else? 21+ only. O’Brien’s is a cash-only venue, though they do have an ATM.

Costumes are fun. Live music is fun. Combine them both, and you’ve got O’Brien’s Halloween Night Cover Show. Check out members of local bands, costuming – and performing – as other, less local bands, to create one of the best things to do in Allston Halloween night.

Nice Guys and Jim Leonard combine to form Devo, while members of Horse Girl and Halfsour become Polaris (from the Pete and Pete soundtrack) before your eyes. Croon the night away, as members of Black Beach and Puppy Problems join forces to become Bright Eyes. It’s a great time at a fun location: so if you’re looking for a Halloween party that literally rocks, you don’t have to go far.

Ghost Tours by Ghosts & Gravestones

Where: Ghosts & Gravestones, 200 Atlantic Ave, Boston, MA 02110
When: Heads out daily through to the end of October. Reservations required: call for times.
What’s it going to cost? Around $40 for adults, $35 for children 6-12
Anything else? Children must be at least 6 years old to board the “Trolley of the Doomed.”

Been meaning to take a guided tour of Boston’s history, but find the standard historical approach too subdued for your taste? Climb aboard the Ghosts & Gravestones nighttime trolley, and experience some of Boston’s most haunted sites, and hear the blood-curdling tales that most tours omit from the record. With tours running every day through the end of October, you can throw together a spooky night out whenever your schedule permits.

You’ll be heading out to the waterfront for this “fright-seeing” tour, which is about 30-40 minutes from Allston via the 501. And you’ll be right at Boston Harbor before and after the tour, so if you fancy a seafood dinner before your tour, you’ve got the makings of a memorable, spooky night out in Boston.

Miracles & Other Deceptions

Where: Omni Parker House, 60 School St. Boston, MA 02108
When: Fridays at 7:00 PM & 9:00 PM
What’s it going to cost? $60 general admission, $75 VIP “At The Table” front row seat
Anything else? Recommended age limit is 13 and older

While it isn’t exclusive to the haunted season, there are few better times to see this Vegas-quality magic act than in the heart of October. Award-winning stage magician Paul Gertner crafts bespoke illusions Friday nights in Boston, famously bringing the illusions that have fooled Penn & Teller…twice. Shows of this caliber are a rare sight this far from Sin City, but Gertner always delivers in spades. Literally.

About a half an hour via the 501 or 45 minutes on the Green Line, Miracles & Other Deceptions makes a fantastic centerpiece to an October night on the town

Bringing Spooky Back

Everybody loves Boston in the fall, but this is a special time of year. We think that these are among the best things to do for Halloween in Boston, but what do you think? Did we miss something? Should we look at a wider variety of Boston Halloween activities? There’s no need to bare your fangs at us if we missed your favorite: let us know in the comments below.

Happy Halloween, Boston!

Demetrios Salpoglou

Demetrios Salpoglou

Published October 22, 2019

Demetrios Salpoglou is the CEO of which is an information and technology based services company that provides cutting edge resources to real estate companies. Demetrios has developed over 90 real estate related websites and owns hundreds of domain names. Demetrios also owns and operates six leading real estate offices with over 120 agents.

Demetrios has pulled together the largest apartment leasing team in the Greater Boston Area and is responsible for procuring more apartment rentals than anyone in New England – with over 130k people finding their housing through his services. Demetrios is an avid real estate developer, peak performance trainer, educator, guest lecturer and motivational speaker.