Ghosts and Gravestones Tour
WHAT: These spooky trolleys drive around Downtown Boston throughout the year, but Halloween is prime time to hop on board. The hour-and-a-half-long ride takes visitors to some of the most haunted sights in the city, including the Omni Parker house and King’s Chapel. Just don’t literally jump out of your seat—this thing drives in the actual street.
WHERE: Downtown Boston
WHEN: Tours can be scheduled seven nights a week at 7 pm, 8 pm or 9 pm
Pinball Witch Hunt Halloween Extravaganza
WHAT: In which your friends from DigBoston (read: us) present you with a night of comedy, horror, and trivia with a costume contest and prizes. Featuring Lamont Price (Hulu, 2 Dope Queens, Boston’s Best Comedian 2018) and other comics seen on MTV and Comedy Central.
WHERE: Down the Road Brewery, Everett
WHEN: Oct 24
Pumpkin Palooza at the Lawn on D
WHAT: As the Lawn on D wraps up another season, it’s time to celebrate with two days full of Halloween festivities. Past such events have brought us live music, LED dancers, pumpkin carving, and face painting. More spooky details about this year’s event will be released soon.
WHERE: South Boston
WHEN: Oct 27-28, all day
Fenway Friday Night Halloween Pub Crawl
WHAT: Pub crawls are everywhere in Boston, and Halloween is no exception. There are a lot to choose from, but this one appears to involve goblins, werewolves, and goons lurking nearby, and they’re all a ton of fun to drink with.
WHEN: Oct 27
WHAT: If you’re not a dog person, you are the real monster. For those who love animals, this event features the cutest pups around strutting their stuff in tiny costumes, all while they parade for half a mile alongside the Charles River. It may not be the scariest, but it’s definitely the cutest.
WHEN: Oct 28, noon-2 pm
WHAT: These badass ladies are ditching the blood and gore to dress up with glitter and glitz. Celebrate Halloween with these former RuPaul’s Drag Race contestants offering a smorgasbord of stand-up, music, drinks, and of course, killer looks.
WHERE: Royale, Boston
WHEN: Oct 31, 8 pm
WHAT: Anyone can sit down and read The Crucible, but seeing the events unfold in front of you is a whole other experience. Cry Innocent brings the infamous 1692 witch trials to life live on stage, in the spot where they took place more than 300 years ago. It’s a unique horror guaranteed to bring more chills than your upcoming heating bills.
WHERE: Old Town Hall, Salem
WHEN: Shows run seven days a week
Pumpkins and Pints
WHAT: Forget a pumpkin spiced latte, we’re skipping right to beer. This celebration features seasonal food and drinks, and you know what that means—Oktoberfest brews from local and international distributors.
WHERE: Glasshouse, Cambridge
WHEN: Oct 13, 3-7 pm
Festival of the Dead
WHAT: This annual fest runs through the whole month of October, earning Salem its reputation as one of the best places to celebrate Halloween anywhere, if not the best. You can really do it all—have a psychic tell your future, or just go and experience the local rituals while dancing all night at the Official Salem Witches Halloween Ball.
WHEN: Month of October, different events
Boston Costume Dash
WHAT: Trick-or-treating is fun, but a bit childish, right? Well, you can still put on a silly costume, but instead of feasting on candy, you can burn off calories by running. This 5K is different from most, of course, since participants will be running in costumes. Including some who will presumably be dressed as runners, which could be somewhat confusing.
WHERE: Copley Square
WHEN: Oct 27, 9 am
Nightmare on Boston Harbor
WHAT: Sail along the Boston Harbor on a party ship, because why the heck not? The Providence II will be stocked with DJs, beats, booze, and hundreds of people who are more decked out than you. Get it, decked out!?
WHERE: Seaport, Boston
WHEN: Oct 27, 7-10 pm
Tales from the Crypt
WHAT: King’s Chapel is one of the rare churches in the northeast that contains crypts, aka the remains of dead people. Candlelit tours are led in the cellar where relics are stored, making it so history buffs and necromaniacs can gawk at the opportunity to explore the historic landmark.
WHERE: King’s Chapel, Downtown Boston
WHEN: Oct 19-23, 25-27, 29-31. Tours offered at 5:30 pm and 6:15 pm
WHAT: Want to scream and laugh at the same time? ImprovBoston’s annual musical is about a fake reality TV show where the characters compete in dangerous games, indulge in romance, and much more. In the meantime, audience members are splattered with fake blood as actors make them a part of the show. The performance is not for the squeamish, but if blood and guts are your thing, this is your scene.
WHERE: ImprovBoston, Central Square, Cambridge
WHEN: Performances Oct 19-31, times vary