Halloween Weekend Guide: Oct 27–29th, 2017 | Portland Old Port

Halloween Weekend Guide for Oct 27th – 29th, 2017

We wouldn’t dare let you go into this Halloweekend as blind as a headless horseman! We’ve got lots of creepy things for you to crawl throughout this weekend in true Portland Old Port style…


Starting at 5:30, THE GHOUL OF ROCK: MAMM’s Halloween Bash at One Longfellow Square will begin! Tickets are now $12 to this creepy all-ages costume party that’s sure to terrify!

Not only is it Halloweekend, it’s also the Fourth Friday of the month, which means the Dapper Gents will be gracing Rhum with their music from 8 on! Bring your grass skirt and your mustache, you’re good to go!

The Covered in Bees’ Halloween Spooktacular, taking place at 9 pm at Empire Live Music & Events will feature live local bands, costume contests, prizes and more!

If you’re a Fat Knuckle Freddy Fan, you’re in luck! They’ll be releasing 2 CD’s at the Portland House of Music & Events at 9 pm in the company of their local music friends (and their musical talents!)


Take a ride on the Pumpkin Train from 9:30 am until 4 at the Maine Narrow Gauge Railroad Co. & Museum. Bring the kids to explore the museum and paint a pumpkin as a souvenir!

Night of the Living Beer/Zombie Dance Party/Portland Craft Cask Night is back at Oxbow from 5pm-midnight! You don’t want to miss some local favorite casks from Allagash, Austin Street, Banded Horn, Bissell Brothers, Liquid Riot, Rising Tide, and a few of Oxbow’s own!

The Maine Historical Society’s annual Haunted House Tour of the Longfellow House (adults only please!) evoking all of the family members that died in the house. This hour-long tour is followed by drinks and snacks in the house!

Just because the temperatures have dropped, doesn’t mean we’ve got to stop Booze Cruising! The Popsickel Boat Party sets sail at 6:30 and won’t disappoint! Celebrate Halloween in true Portland style- on the water! And don’t you dare forget that costume!

Meander down to Thompson’s Point for some pregaming at Stroudwater Distillery & a bite at Big J’s Chicken Shack before the Otherworld Circus, Halloween Ball at Brick South! Six hours of music from different DJ’s and artists, Circus Maine, live video projections for an immersive mixed media dance party, 3 bars, and one VIP section… We’ll be surprised if you don’t buy a ticket by the end of this sentence.

The Spirit of Halloween Bash begins at 8 pm at the Portland Expo. Expect live music, a fully stocked bar, and a costume contest (you might consider participating… $1,000 in prizes up for grabs!)

Local band The Awesome will be playing at the Portland House of Music and Events at 8 pm, it should make for one of the most awesome Halloween parties of the weekend!

Fans of the artist formerly known as Prince rejoice at Port City Music Hall for Purple Brainz 5: A Halloween Prince Tribute. This event is 18 and over and will be $18 for a ticket at the door!

The Illuminati Ball is back at Empire Live Music & Events with the likes (and music) of Vapors of  Morphine & SeepeopleS. Complete with all things creepy, obscene & mysterious, dress in your best costume for this event as the most stunning costumes will win great prizes!


The Portland Comic Expo begins at 10 am at the Portland Exposition Building. Comic artists, guests, dealers, programming, and cosplayers, oh my! Come dressed as your comic character, and bring the whole family!

What better way to end Halloweekend than with Michael Jackson’s Thriller? Join LQH at Empire Live Music & Events to pay tribute to the King of Pop… Extra points if you’re in costume & know the whole routine! The dancing starts at 8.

Matt Schofield will be playing at One Longfellow Square starting at 8 pm. Tickets are $20 in advance and $25 at the door if you’re in a bluesy mood!

Thrill seekers and history buffs alike, meet up at Bel Buoy Park at 8 pm for a Wicked Walking Tour throughout the Old Port, filled with Abenaki Attacks, Witch Trials, Pirates, and more!

Geno’s Rock Club is hosting the ultimate Halloween Bash! Featuring Hessian Maine, Problem with Dragons, and Drivetrain, the doors open at 9:30, $8 to enter and only $6 if you’re in costume!