Get ready for a hauntingly good time this weekend in Portland, as Halloween festivities take center stage!
Join the eerie excitement at the Phantom of the Opera silent film screening at Congress Square Park, or dance the night away at Bissell Brothers’ Fright Night bash. For a family-friendly outing, don your best costume at the East Bayside Halloween Fest, featuring pumpkin carving and live music. If you’re saving your spooky celebrations for later, there are still plenty of autumn activities to enjoy, like the Portland Ghost Walk, which dives into the city’s haunted history. Embrace the Halloween spirit!
Here’s The Weekend Guide for Friday, October 25th – Sunday, October 27th, 2024
Friday the 25th
Harvest on the Harbor – From the Sea: A Culinary Voyage + Oyster Shucking Competition | O’Maine Studios | 6:00 PM Doors
As part of the annual Harvest on the Harbor, this ocean-themed evening is a must for seafood lovers, offering a taste of Maine’s coastal bounty. Kick things off at 6:30 pm with a lively oyster shucking competition, courtesy of Lady Oyster, where you can cheer on your favorite local shuckers. Sip on a wide range of beverages, from Zardetto Prosecco to Austin Street Brewing beer, and enjoy specialty sips from Root Wild Kombucha and Coffee By Design. Treat yourself to savory bites from Browne Trading, SoPo Seafood, and more, with ocean-fresh flavors that capture Maine’s culinary essence. Plus, don’t miss the chance to shop unique, ocean-inspired goods from Cold Current Kelp and Planet Botanicals. Exclusive 21+ event. Tickets.
5 Year Celebration | Congress Bar & Grill | All Weekend
Congress Bar & Grill is marking five fantastic years with a weekend-long celebration! All weekend they’ll be rolling out discounted food, offering some of your favorite dishes at special prices. To make things even more fun, they’re bringing back classic cocktails from their early days, so you can sip on some nostalgia while toasting their success. Whether you’re a longtime regular or a first-time visitor, this anniversary bash is the perfect time to drop by and raise a glass to five years.
Fright Night | Bissell Brothers | 8:00 PM – 12:00 AM
Bissell Brothers’ Fright Night is back, and it’s bigger and spookier than ever! Don your best costume and join the fun, with a lively costume contest and a dance party all night long. DJ Keystone will be spinning the beats from 8 pm until midnight, setting the perfect eerie vibe. Whether you’re in it for the contest, the dancing, or just the brews, this is the place to be for a hauntingly good time!
For more Halloween events check out our Halloween Guide!
Music Bingo | Freedom’s Edge Cider | 6:00 PM – 7:30 PM
Freedom’s Edge Cider is hosting a special Music Bingo night to support the New England Breast Cancer Alliance, their nonprofit partner for Breast Cancer Awareness Month. For just a few dollars per card, you can join the fun—listen for the songs, mark your squares, and shout BINGO for a chance to win prizes! Plus, $1 from every drink special purchased throughout October will be donated to support breast cancer research and survivors. It’s a great way to have fun while contributing to an important cause.
The Hunchback of Notre Dame with The Kotzschmar Organ | Merrill Auditorium | 7:00 PM – 9:30 PM
Celebrate Halloween with a spine-chilling journey into the 1920s as The Hunchback of Notre Dame, starring Lon Chaney, comes to life once more. Paired with the haunting melodies of the Kotzschmar Organ, played live by James Kennerley, the music will mirror the suspense and drama of this silent film classic. Drawing inspiration from composers like Louis Victor Jules Vierne, Kennerley’s performance promises to immerse you in a world of gothic wonder. Costumes are encouraged, so come dressed for the occasion and enjoy an evening of history, horror, and musical mastery. Tickets.
Saturday the 26th
Trick-or-Treat Exchange Street | Exchange Street | 1:00 PM – 3:00 PM
The businesses of Exchange Street are back for their 3rd annual family-friendly trick-or-treating event! On Halloween, bring your little ghosts and goblins (ages 0-10ish) downtown for a fun and free trick-or-treating experience. Dress up the entire family—including your pets—in their best costumes and visit local businesses such as The Maine Souvenir Shop, D. Cole Jewelers, Sherman’s Books, and more for sweet treats. Just look for the orange posters and window signs to spot the participating locations.
East Bayside Halloween Fest | East Bayside | All Day
A full day of spooky fun at the East Bayside Halloween Fest, returning for year 4! Businesses throughout the neighborhood will offer food and drink specials, along with festive activities like pumpkin carving, costume contests, and live music. Be sure to swing by Rising Tide Brewing for the ever-popular Dog Costume Contest and explore the Spooky Fête Market at Austin St. Brewery. It’s a perfect opportunity to come together with the community, enjoy the Halloween spirit, and help raise funds for Maine Needs. Don’t miss out on this neighborhood-wide celebration!
More Women + Surf Fundraising Party | Atlantic Farms | 3:00 PM – 8:00 PM
Celebrate another incredible season with the women of More Women + Surf at this lively fundraising party! Enjoy a complimentary beer from Hi-Fidelity Beer with your ticket, plus a stainless steel cup from Never Better Collective and a raffle ticket for some exciting prizes. The event will feature delicious eats from Quiero Café, Back River Blends, and Maiz Colombian Street Food, and live music from local bands Pretty Everyone and Falkyn. Plus, explore the work of talented local artists like Jordan Kendall Parks, OTECA, Christine Jozitis, and Swell Affair. It’s a perfect evening to connect with the community and support a great cause! Tickets.
Hoot & Howl: Family Halloween | Children’s Museum & Theatre of Maine | 9:00 AM – 1:00 PM (Repeats Sunday)
Get ready for a HOOTING good time at the Children’s Museum and Theatre this Halloween season! Children and their caregivers are invited to a series of not-so-scary Halloween celebration events for children and their families. Expect a range of activities that will invite you to hoot & howl your way through museum exhibits, including indoor trick-or-treating, exploring spine-tingling animal artifacts and specimens, meeting misunderstood characters in a special interactive performance at Maddy’s Theatre, and creating creepy crafts in the MakerSpace. Tickets.
Annual Halloween Jam | Portland Skate Park | 4:00 PM – 7:00 PM
Sal’s Skate is hosting its Annual Halloween Jam, and this year’s event is raising funds to light up Dougherty Park! The event will feature gear giveaways from WKND Skateboards and shoes from NB Numeric, a costume contest, food, and music, so you won’t want to miss out! Half the park will be lit up after sunset for a killer skate session, and every dollar raised goes directly towards adding lights to Portland Skatepark. Join the fun and support the future of your local skate scene! GoFundMe.
DeadBeat | Gritty McDuff’s Brew Pub | 8:00 PM – 11:00 PM
DeadBeat is bringing their Grateful Dead tribute show to Gritty McDuff’s in Portland for the very first time! From 8-11 PM, enjoy an evening filled with your favorite Dead tunes as the band rocks the house with their signature jam band vibe. This show is free—no cover charge! Grab a drink, gather with fellow Deadheads, and experience a night of live music. 21+ event.
Halloween Bash | Definitive Brewing Co. | 4:00 PM – 11:00 PM
Definitive Brewing Co. is pulling out all the stops for their Halloween Bash, offering something for everyone! The evening kicks off with all-ages fun from 4-8 PM, including trick-or-treating for the kids, a costume contest at 4:30 PM with categories for ages 0-12 and 13-18, and a 5 PM screening of Hocus Pocus. Later, the event shifts to a 21+ “Definitive After Dark” bash from 8-11 PM, featuring a horror DJ set by DJ Diego, dancing, and an adult costume contest at 9 PM with a $100 gift certificate for the winner. Psychic readings, courtesy of Mystical & Whimsical Events, will be available from 6-10 PM, and Fat Kid Culinary Productions will be on hand serving up delicious eats. It’s a spooktacular night you won’t want to miss!
Sunday the 27th
Tarot Card Readings | Botanically Curious | 12:00 PM – 2:00 PMStep into the mystical world of tarot every Sunday at Botanically Curious with Lunalux Botanicals! Whether you’re seeking guidance, clarity, or just a fun, introspective experience, their tarot card readings offer a chance to explore your inner thoughts and future possibilities. With an inviting atmosphere and expert readers, it’s the perfect way to spend a Sunday afternoon. Come by, relax, and let the cards reveal what the universe has in store for you!
MAMM Presents: Ghoul of Rock | One Longfellow Square | 12:30 PM
Forget “School of Rock”…get ready for “Ghoul of Rock”, a spine-tingling night of music as Maine Academy of Modern Music’s (MAMM) presents “Ghoul of Rock”! This all-ages Halloween bash at One Longfellow Square is the ultimate costume party, featuring MAMM’s student rock bands delivering electrifying performances that will melt faces. Costumes are highly encouraged, so don your spookiest attire and get ready to rock out with some of Maine’s most talented young musicians. It’s a frightfully fun way to kick off the Halloween season! Tickets.
Maine Down Syndrome Buddy Walk | Payson Park | 12:30 PM
Join Maine Down Syndrome Network in the celebration of Down Syndrome Awareness Month at the Maine Down Syndrome Buddy Walk and Festival! This heartwarming event brings together Mainers with Down syndrome, their families, and friends for a day of fun and support. In addition to the walk, enjoy games, music, and a special October twist—costume contests and trunk-or-treating! It’s a great opportunity to come together as a community, make lasting memories, and support a meaningful cause. Be sure to register or fundraise in advance to be part of this joyful event! Donate + Register.
Portland Ghost Walk | State Theatre | 8:00 PM – 9:30 PM
Step into the eerie side of Portland’s Old Port with a guided 90-minute ghost walk that delves into the city’s spookiest tales. Starting at DiMillo’s Marina, this tour reveals chilling accounts of apparitions, psychic detectives, and even a haunted pool table. Explore the historic waterfront, where stories of supernatural encounters abound—like the unsettling sight Midshipman Edward Preble witnessed in Casco Bay in 1779. From sea serpents to ghostly figures, this haunted stroll through Portland’s iconic neighborhood will leave you with goosebumps as you uncover its darker history. Tickets.
Silent Movie: Phantom of the Opera | Congress Square Park | 6:00 PM – 7:30 PM
Wrap up the Halloween season with a screening of the classic silent film Phantom of the Opera in Congress Square Park, presented by Friends of Congress Square Park. This final movie of the season promises a night of eerie entertainment under the stars. Arrive early to hear from local horror movie podcasters Speak All Evil as they dive into the film’s impact on the horror genre. Costumes are encouraged, so dress up and enjoy this unique, spooky outdoor movie experience!
For more events head to our Events Calendar here.