Boston Frog Pond Pumpkin Float: Bring the whole family to the fourth annual Pumpkin Float right in the heart of the city. If you bring an 8-inch jack-o-lantern, the Frog Pond staff will illuminate it and set it afloat. Watch as the pond fills up with glowing pumpkins throughout the evening.
Free, Friday, Oct. 20 5 p.m. Boston Common Frog Pond, 38 Beacon St., Boston, bostonfrogpond.com.
Halloween-Themed Toddler Tuesday: Little ghosts and ghouls are invited to Boston’s LEGOLAND Discovery Center for Halloween activities. Spooktacular story time, a Halloween-themed DUPLO build, and mingling for parents are all on deck.
$16, Tuesday, Oct. 24, LEGOLAND Discovery Center Boston, 598 Assembly Row, Somerville, legolanddiscoverycenter.com.
Pumpkin Palooza: For one day, the Lawn on D will transform into a Halloween town. Kids can carve pumpkins, learn circus tricks, and compete in a costume contest during the day. Once night falls, dance shows and live music will take over the space.
Free admission, Saturday, Oct. 28, Lawn on D, 420 D St., Boston, facebook.com.
Magical Halloween Castle and Celebration on Castle Island: Fort Independence will turn into a kid-friendly Halloween castle all Halloweekend long, weather permitting. Organizers say the fort inspired Edgar Allen Poe to write his famous “The Cask of Amontillado”—so beware of any vaults.
Free, noon, Saturday, Oct. 28 and Sunday, Oct. 28, Fort Independence, 2010 Day Blvd., Boston, bostoncentral.com.
Canine Promenade on the Esplanade: Is your dog a secret werewolf? A vampire whose bite is worse than his bark? Join the Esplanade Association for a half-mile Halloween costume parade along the Charles River. Spectators can watch for free, but dogs must be registered before the event.
Free, noon, Sunday, Oct. 22, Charles River Esplanade, Boston, esplanadeassociation.org.
Halloween Pet Parade and Costume Contest: If your dog’s costume was top-notch and you’re feeling a little competitive, you’re in luck. Enter your pup in Faneuil Hall’s annual parade and costume contest. Prizes are awarded for best of show, best owner-pet combo, best local representation, and most creative.
Free, noon, Saturday, Oct. 28, Faneuil Hall Marketplace, 4 South Market St., Boston, faneuilhallmarketplace.com.
WholeTone Opera’s The Werewolf: A cursed loup-garou is terrorizing a quiet village and seducing young brides. Comedy, horror, and sideways romance are all on deck at the Rockwell’s new opera. Every performance will feature a surprise opener to boot.
$18-45, various times,Friday, Oct. 20 and ongoing, the Rockwell, 255 Elm St., Somerville, eventbrite.com.
Cirque of the Dead: Laugh your head off (figuratively) at this circus extravaganza. With demons, witches, and monsters as performers, audiences will get close and personal with the acrobats. Be careful, though—you could end up a victim of some bloodthirsty creature. Don’t stand too close to the “splash zone.”
$30-50, multiple times, Friday, Oct. 20 and ongoing, OBERON, 2 Arrow St., Cambridge, americanrepertorytheater.org.
Bistany’s Mysteries: Novelist Matthew Bistany is writing his latest mystery, and he needs a co-author. Audience members make up plotlines on the spot. Create, then navigate, spooky twists and turns to figure out who the killer is.
$18, 10 p.m., Friday, Oct. 20 and Friday, Oct. 27, ImprovBoston, 40 Prospect St., Cambridge, eventbrite.com.
Improv Asylum Halloween Show: Join Improv Asylum’s Main Stage for performances about the best and worst parts of the year’s spookiest holiday. Every show is different, so prepare yourself for thrills, chills, and plenty of laughter.
$15-33, various times, Wednesday, Oct. 26 and ongoing, Improv Asylum, 216 Hanover St., Boston, improvasylum.com.
Strange Inspirations: Netflix’s Stranger Things will release its second season at midnight on Oct. 27, so binge before this series begins 16 hours later. The Brattle Theatre will show films that have influenced the streaming series, including Close Encounters of the Third Kind, Ghostbusters, and A Nightmare on Elm Street.
$9+, various times, Thursday, Oct. 27 and ongoing, Brattle Theatre, 40 Brattle St., Cambridge, brattlefilm.org.
Halloween Horror Marathon 2017: Twelve nonstop hours of ghouls and gore will take over the big screen at Coolidge Corner Theatre. Starting at exactly midnight, hunker down in your seat for bloodcurdling classics like Zombie and Night of the Living Dead on 35mm film. You can also watch a double feature, then head home to get some sleep (if you can).
$25-30, midnight, Saturday, Oct. 29, Coolidge Corner Theatre, 290 Harvard St., Brookline, coolidge.org.
The Boston Pops: The Nightmare Before Christmas: Start your Halloweek off right with two performances by the Boston Pops under the direction of Keith Lockhart. The orchestra will play the entire score to Tim Burton’s classic 1993 film alongside a screening. Before the performance, hit Symphony Hall’s spooky spots for trick-or-treating.
$45-95, 8 p.m., Monday, Oct. 30 and Tuesday, Oct. 31, Symphony Hall, 301 Massachusetts Ave., Boston, bso.org.
Halloween Masquerade: It’s a Cinderella story. Don your best formalwear for an elegant evening to benefit Tenacity, a nonprofit that integrates youth academic and fitness programs. Masks are optional, but strongly encouraged.
$100, 7:30 p.m., Saturday, Oct. 21, Algonquin Club, 217 Commonwealth Ave., Boston, tenacity.org.
A Stranger Evening: An Original ’80s Halloween Party: Like, totally spooky. Throw it back to the 1980s with Kimpton Marlowe Hotel and Bambara Kitchen & Bar. Nods to Netflix’s Stranger Things will include Eleven’s Eggo waffles and a Demogorgon cocktail. Are you in Cambridge or the Upside Down?
$65.11, 7:11 p.m., Friday, Oct. 27, Kimpton Marlowe Hotel, 25 Edwin H. Land Blvd., eventbrite.com.
Halloween pARTy: Paint the town black and orange—or at least take a gander at original works by local artists. This art-themed Halloween party will feature unique creations, a signature cocktail, a costume contest, and more. All artwork will be available for purchase.
$25, 7 p.m., Saturday, Oct. 28, Brookline Arts Center, 86 Monmouth St., Brookline, brooklineartscenter.com.
Carrie Halloween Party: Would you survive Carrie’s senior prom? At the Liberty Hotel, you can find out. Come in costume, dine from an a la carte Carrie-themed menu, and watch out for anything suspicious—you never know who might have rigged buckets of pigs’ blood over your head.
$62+, 8 p.m., Saturday, Oct. 28, Liberty Hotel, 215 Charles St., Boston, showclix.com.
Boston’s Annual Halloween Gala: A Benefit for Hurricane Relief: Halloween is set to take over the Seaport with an “experiential production” from designer Samuel Vartan. Equal parts elegant and terrifying, this year’s gala will benefit the work of American Red Cross in Texas, Florida, and Puerto Rico. Partying for hurricane relief? That’s scary good.
$95, 8 p.m., Saturday, Oct. 28, Boston Convention and Exhibition Center, 415 Summer St., Boston, bostonsannualhalloweengala.com.
“Titanic Masquerade” Halloween Party Cruise: It’s Boston’s most luxurious yacht—just hope there are no icebergs in the harbor. For one night, the Spirit of Boston will transform into a resurrected Titanic. Be sure to accept if a ghostly guest asks you for a dance.
$45+, boarding 11 p.m., Saturday, Oct. 28, Seaport World Trade Center, 200 Seaport Blvd., Boston, halloweencruises.com.
“The Black Pearl” Halloween Party Cruise: Pirates and wenches, climb aboard the Boston Harbor’s most infamous ship. With plenty of DJs, dancing, and bottles o’ rum, you’ll be sure to have an exciting evening. Costumes are strongly encouraged.
$20+, boarding 8:30 p.m., Tuesday, Oct. 31, Seaport World Trade Center, 200 Seaport Blvd., Boston, halloweencruises.com.
Beer Mansion by Brooklyn Brewery: Get boo-zy and peruse five themed tasting rooms in a bona fide beer mansion. “The Forest,” “The Darkness,” and “The Anatomy of a Beer” are just three of the flavors on tap during the two-day event (although tickets to Saturday’s sessions are already sold out). Partygoers will also get access to food, live music, art, games, and other surprise activities.
$50-60, 6 p.m., Friday, Oct. 27, Boston Center for the Arts, 539 Tremont St., Boston, brooklynbrewerymash.com.
Pre-Halloween Bash with Dingonek and Cocek: Even though Halloween is really a month-long holiday, Aeronaut Brewery is pulling out all the stops for this party. Get competitive with a costume contest, drink beer on tap, and dance to Dingonek Street Band and Cocek Brass Band.
Free admission, doors at 5 p.m., Friday, Oct. 27, Aeronaut Brewery, 14 Tyler St., Somerville, thebostoncalendar.com.
Great Pumpkin Festival: It’s the Great Pumpkin Festival, Beantown! The Cambridge Brewing Company will have pumpkin-flavored beers from across the country, curated by Brewmaster Will Meyers. If the beer garden is sincere enough, the Great Pumpkin may even stop by one of the three sessions.
$30+, 12 p.m., 4 p.m., and 8 p.m., Saturday, Oct. 28, Cambridge Brewing Company, 1 Kendall Square, Cambridge, thebostoncalendar.com.
Grown-up Trick or Treat: It’s not just for kids. Adults can join Cocoa Beantown for costumed chocolate tours in Back Bay and the South End. Taste some spooky treats from curated chocolatiers, and win extra chocolate—plus a mysterious grand prize—if your costume is sweet enough.
Back Bay: $50, 10 a.m., Saturday, Oct. 28, Gourmet Bouquet, 10 Huntington Ave. Boston, South End: $50, 2 p.m., Code 10, 1638 Washington St., Boston, cocoabeantown.com.
Boston Costume Dash 5K: Who can run faster, Frankenstein or Pikachu? Find out by racing through Back Bay in full costume. After the run, keep the party going with a costume contest and swag in Boston Common, followed by a pub crawl.
$45+, 9 a.m., Saturday, Oct. 28, Copley Square, Boston, costumedash.com.
Costumes for Cancer 5K Run and 2.5K Walk: Bring the whole family for a race around the Chestnut Hill Reservoir. Stick around for trick-or-treating, a costume contest, and finish line treats. Proceeds will benefit the John Estrella Foundation for Cancer Research, which provides research grants to Mass General Hospital.
$28, 10:30 a.m., Sunday, Oct. 29, Chestnut Hill Reservoir, 400 Chestnut Hill Ave., Brighton, racewire.com.
Horror Yoga Flow and Ghostly Cocktails: Specialty yoga classes are taking over Boston, and Halloween is no exception. Join Bully Boy Distillers for costumed yoga to classic horror hits, then sample some handcrafted cocktails. Who said the monster mash wasn’t a yoga pose?
$21, 2 p.m., Sunday, Oct. 29, Bully Boy Distillers, 44 Cedric St., Boston, eventbrite.com.
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