Are you ready for the frighteningly fun weekend that’s ahead? Getting us in the “spirit” of one of the most celebrated and beloved holidays, the city has come alive this weekend with spooky events and gatherings such as Halloweenfest, Fright Night, Trick-or-Treat Exchange Street, Halloween Costume Cruise, Scary-oke and more! Check it all out!
For the full Halloween Events Calendar + Guide head to our breakdown here.
Here’s the Weekend Guide for Friday, October 28th- October 30th, 2022
Trick-or-Treat Exchange Street | Portland Old Port | 3:00 PM – 6:00 PM
The businesses of Exchange Street have come together for their first annual family-friendly trick or treating event! Visit downtown Portland for this free event for children ages 0-10ish. Dress the entire family, including pets, in adorably scary costumes and haunt local businesses for a sweet treat. Look for the orange posters and window signs to know which businesses are participating this year!
Friday the 28th
Harvest on the Harbor: Meet Your Maker | O’Maine Studios | 5:30 PM – 7:30 PM
Harvest on the Harbor delivers a series of individual, ticketed events over three days, including Meet Your Maker, featuring locally-made Maine Distillers Guild spirits. On Friday, come and meet the makers, try cocktails made with local gins, vodkas, bourbons, rums, and more, plus a variety of food pairings to complement the huge selection of spirits. This is a 21+ event. Tickets here.
Halloween Costume Cruise | Fogg’s Water Taxi and Charters | 5:30 PM – 8:00 PM
Kick off Halloween weekend with Feel Good Portland’s second annual Halloween Costume Cruise on board the Casco Bay Cat! Will include a live DJ and a couple of costume prizes for best dressed! (BYOB 21+). Tickets here.
Mali Obomsawin 6tet: “Sweet Tooth” Album Release Show | Portland Conservatory of Music | 8:00 PM
Mali Obomsawin’s debut album as composer-bandleader, “Sweet Tooth,” out on October 28th! Those in attendance will be the first to hear the finalized arrangements live and have a chance to buy the record. Featuring original compositions and ancient Wabanaki songs, a little bit Alice Coltrane, a little bit Albert Ayler. The compositions reveal threads that bind together blues, jazz, hymns, folk songs, and Native cultures, and foreground the breadth and continuity of Indigenous contributions to these genres. Tickets here.
The Vista Cruisers | Gritty McDuff’s | 9:30 PM
Scary-oke Night | Stroudwater Distillery | 7:00 PM – 10:00 PM
It’s time to get spooky at Scary-oke Night at Stroudwater! Join them on Halloweekend for a spooky edition of karaoke! Costumes encouraged and first hour singers get a drink on the house! Always a fun time, so make sure to stop by! Drink specials and specialty shots. 21+ to enter. Tickets here.
Saturday the 29th
Spooktacular Songs & Storytime | Merrill Auditorium | 10:00 AM – 1:00 PM
A kid-oriented Halloween event at Merrill Auditorium, co-presented by Friends of the Kotzschmar Organ, City of Portland, and Portland Public Library, the event will feature stories, songs, and a book-mobile from the Portland Public Library Children’s Librarian, a 10 minute “Mickey Mouse and the Haunted House” film with organist James Kennerley, an awesome kid-friendly demonstration of the (very cool) Kotzschmar Organ, and a costume parade across the stage of Merrill Auditorium for all of the kids. Costumes are encouraged, and reservations for this FREE event are required. Register here.
Veg Fest | East End Community School | 11:00 AM – 3:00 PM
The Maine Veg Fest is FREE and will consist of a half day of vegan food, speakers, exhibitors, and a raffle. Speakers include: Avery Yale Kamila for “Three Hundred Years of Hidden Vegan & Vegetarian History in Maine”, Brendan Walsh “For Those Who Can’t – Breaking Stigmas and Records on a Vegan Diet”; Clare Beverage at 2 pm for “The Magnificent Mushroom: An Introduction to the Nutrition, Preparation, and Home Cultivation of Mushroom”, and more. Food trucks on-site will include Totally Awesome Vegan Food Truck, Falafel Mafia, and The Greenhouse. Additional food from Asmara Restaurant.
Fright Night | Bissell Brother | 7:00 PM – 11:00 PM
FRIGHT NIGHT is here! Bissell Brothers will be closing the taproom early and transforming it into something wicked: a decked out, 21+ ONLY, after hours Halloween bash. No cover, $5 drafts, DJ sets by Tylord and their very own Desert Wax, a costume contest with prizes for the winners, and special edition spOoOoky party cups. Plus, the first 50 cursed souls in the door get a drink ticket on BB.
Come and visit the many businesses of Portland’s East Bayside as they partake in the 2nd Annual East Bayside Halloween Fest. At Austin Street Brewery there will be face painting and eats and treats from George’s North Shore and Portland Cake Company, while Goodfire Brewing will be hosting a Pumpkin Carving Contest! Breweries and business all across the neighborhood will be donating a portion of their sales to Maine Needs. All day festivities include food trucks, costume contests, dance parties, music, and more!
Halloween Party | The Porthole | 8:00 PM – 11:30 PM
Join The Porthole for a scary good time! They will be giving away a ton of great prizes for their costume contest, so bring your spookiest, funniest, all-out costumes! Boogey down to live music from Spy Glass from 8pm – 11pm. Call up your boo and some friends and tell them to meet you at the Porthole for a ghoul time!
Fall Market & Meet the Makers | Fork Food Lab | 12:00 PM – 4:00 PM
This year Fork Food Lab is participating in the East Bayside Halloween Fest by hosting a Fall Market! Sample goods from participating members and friends, enjoy a complimentary beverage with ticket purchase, and meet the makers! Tickets are $10, with 50% of ticket sales and all bar tips to support Maine Needs. Who you will find at the market: Little Brother Chinese Food, Seamade, The Milk Bottle, Sunnyfield Baking, Maine Coast Fishermen’s Association and more. Don’t forget to bring a bag! Tickets here.
Prohibition Party | Three Dollary Dewey’s | 9:00 PM – 1:00 AM
Three Dollar Dewey’s is partying like it’s the 1920’s! You’ll find yourself dancing along side mobsters, flappers, bootleggers, ghosts, and ghouls to tunes brought to you by DJ David Skye. Get your Mug Shot style photos taken at the photo-booth in the back alley, in your best prohibition themed costumes. Gift Card prizes will be awarded to those with the best costumes! Get ready to step back in time!
Sunday the 30th
The Rock & Roll Playhouse Plays Music of Phish for Kids & More | Portland House of Music and Events | 11:00 AM – 1:00 PM
The Rock and Roll Playhouse, a family concert series hosted at historic music venues across the country, performs songs created by the most iconic musicians in rock history. The Rock and Roll Playhouse band offers its core audience of families with children age ten and under games, movement, stories and an opportunity to rock out in an effort to educate children and explore their creativity. The Rock and Roll Playhouse is an early and often first introduction to a child’s lifelong journey with live music and rock and roll. See you at the show! Tickets here.
Dogoween | The Thirsty Pig | 1:00 PM – 3:00 PM
Tell your dogs! The red carpet costume walk-off is returning to The Thirsty Pig. Kidd-o judges and lots of laughs. $5 entry fee that is donated entirely to the Animal Refuge League of Greater Portland.
Walk Among the Shadows: Untimely Ends | Eastern Cemetery | 5:30 PM – 6:15 PM
“Untimely Ends” includes accounts of 18th century medical treatments, pauper’s graves, and burial of visitors from away. This year eight spirits will rise from their graves to recount the tales of their untimely ends at different locations throughout the graveyard. Audience groups will enter from the 224 Congress Street gate every 20 minutes during the event, on a first-come, first-served basis. Each performance lasts about 40 minutes.Tickets here.
Halloween Trivia | Andy’s Old Port Pub | 6:00 PM – 8:00 PM
Join Andy’s Old Port for a night of spooky Halloween-themed trivia. 3 Rounds to beat the crowd, and prizes awarded to top three.
Silent (Movie) Sunday: Nosferatu | Congress Square Park | 5:30 PM – 7:00 PM
Kinonik and Friends of Congress Square Park present the classic German vampire silent film “Nosferatu” on 16mm! Live accompaniment included. They will also be hosting Abraxas for a little pop-up shop of horrors, and will have themed baked goods available for purchase from GrungyTree Treats!
For more events, head to our full Events Calendar here.