11 Fun Halloween Events to Check Out This Year

These festivities are sure to put a smile on your face.

sowa halloween boston south end event

If you’re one of those folks who’s “too old” for Halloween, you can stop right here. Everyone else, get those costumes ready. A lot of fun Halloween events will take place the weekend prior to October 31 this year, so there’s no time to waste—get ready for some frightfully good fun.

Below is just a sampling of the many events happening in the Boston area. Feel free to share your own recommendations in the comments. Happy Halloween!


Outdoor Halloween Events

Halloween at SoWa: “Carnival of Curiosities”

The South End open market’s annual Halloween event—the last outdoor market of the season—is a sight for sore eyes—or gore eyes, depending on the artists’ moods. Not only do the artists dream up and execute elaborate and intricate costumes, but the food trucks get in on the fun too, tricking out their trucks with disgusting and icky decor, but still delicious and yummy dishes.

Free to attend, Sunday, October 26, 10 a.m.-4 p.m., costume contest at 2 p.m. (register before 1 p.m.), 460 Harrison Ave., South End.

4th Annual Canine Promenade

Puppies in costume, what more do you need to know? Activities and giveaways include the half-mile parade, treats, gift bags, and on-site demos. Local pet portrait artist Pawblo Picasso will offer on-the-spot illustrations of your dog. And be creative with those costumes—the competition is stiff. Previous winners in the individual and group categories include a bundle of grapes, the cast of the Wizard of Oz, and his holiness the Pope (and yes, we have photos from last year.)

Free to attend, $15 registration per dog, Sunday, October 26, 12-2 p.m., Fiedler Field on the Esplanade, Boston.

“Punkin’ Fest” at Lawn on D

Southie’s temporary experimental recreation space Lawn on D is hosting a pumpkin-centric, family-friendly Halloween event. Pick a pumpkin from the D Street pumpkin patch to make your own jack-o’-lantern, which you can take home or add to a giant illuminated “Punkin’ Sculpture” that changes its lighting in response to music. Also look forward to punkin’ bowling, music from Poydras Punkins, and pumpkin ale and cider.

Free, Friday, October 24, 4-11 p.m., 420 D St., South Boston.

Pumpkin Drops at MIT and BU

Yeah, so there’s physics and educational value and blah blah blah, anyway… As is tradition, MIT and BU students will drop pumpkins from the tops of buildings. For a preview, check out what happened at Northeastern’s pumpkin drop earlier this month.

MIT Pumpkin Drop: Free, Saturday, October 25, midnight, Green Building at MIT, Cambridge.
BU Pumpkin Drop: Fre, Friday, October 31, 12:30 p.m., Metcalf Science Center at BU, Boston.


Trick-or-Treating Events

Trick-or-Treating and Ghostbusters at Fenway Park

What better place to let your little monsters run wild than at Fenway Park with another Green Monster named Wally? Fenway will host free trick-or-treating on October 30 and follow it up with what will probably be a very hyper screening of Ghostbusters.

Free, Thursday, October 30, trick-or-treating 3-6 p.m., movie at 7:15 p.m., Fenway Park, 4 Yawkey Way, Boston.

Pru Boo

The 20th annual charity trick-or-treat event will raise money for Catching Joy, a nonprofit organization that promotes volunteerism with children and families. Your $4 donation comes with a trick-or-treat bag that kids can take to more than 50 stores and restaurants around the Prudential Center for sweets.

$4 donation, Sunday, October 26, 11 a.m.-1 p.m., Prudential Center, 800 Boylston St., 617-236-3100.

Trick-or-Treat at The Street

One candy apple for you, two sips of wine for me. The Street’s trick-or-treat event will satisfy the kids and the adults as children get complimentary trick-or-treat maps, tote bags, snacks, and free activities, while adults can enjoy discounts and demos at various retailers, plus wine tasting at the Urban Grape. Drink extra responsibly, of course.

Free, Saturday, October 25, 1-4 p.m., The Street, 55 Boylston St., Chestnut Hill.


The Best Neighborhoods and Streets for Trick-or-Treating in Boston


Horror Movies

Halloween Horror Marathon at Coolidge Corner Theatre

The Coolidge’s 14th annual midnight movie marathon will—as always—be a horrific, terrific event. This year, audiences can look forward to Frankenstein, The Lost Boys, and more, with the “more” flicks to be revealed the day of. Strap yourselves in and keep your pulse in check—the full marathon lasts 12 whopping hours.

$20 for double feature, $25 for marathon, Saturday, October 25, 11:59 p.m., Coolidge Corner Theatre, 290 Harvard St., Brookline, 617–734–2500.

Halloween Special Engagements at Brattle Theatre

If 12 straight hours isn’t your thing, consider pacing the horror flick intake with a week of Halloween movies at the Brattle. Starting this Friday, the theater will show films including Rosemary’s Baby, The Whistler, The Tingler, and more. On October 31, catch a 10 p.m. showing of Donnie Darko or the area premiere of Horns.

Prices vary by showing, Brattle Theatre, 40 Brattle St., Cambridge, 617-876-6837.

Nevermore (Live) and Masque of the Red Death (Screen) at Somerville Theatre

Odds are good that the new Edgar Allan Poe statue downtown will see far more visitors as Halloween approaches. Somerville Theatre knows people love Poe’s spooky work, so for Halloween, they’re hosting a live performance, Nevermore, followed by Masque of the Red Death on screen. Thump… Thump… Hear that? It’s your tell-tale heart, saying, “Let’s go! This sounds fun!”

$35 for Nevermore and Masque of the Red Death, or $10 for Masque of the Red Death only, October 31, 8 p.m., Somerville Theatre, 55 Davis Square, Somerville, 617-625-5700.


Six Great Haunted Attractions in Massachusetts