Memorial Day Weekend Guide for May 24th – 27th

Memorial Day Weekend 2019 in Portland, Maine is here! The unofficial start of summer is here and the weather is finally on our side. Enjoy the sunshine and a great line up of events!


Sister Steel is hosting a playshop and performance in Congress Square Park from 6-8 pm! Learn how to play a rhythm on a steel pan drum. Performances by Sister Steel will sandwich the playshop.

The Pete Kilpatrick band will be playing the music of Dave Matthews Band at 9 pm at the Portland House of Music! This is a 21+ event, doors open at 8 pm.

Dance the night away on the Amigo’s patio from 9:30 – 12:30 pm to music from Vinyl Tap!


Have you always wanted to have your own organic garden but didn’t know where to start?! Join fellow beginning gardeners at 409 Cumberland Ave to learn about planning your organic raised bed or in-ground gardens from 10 am – 12 pm.

Head to the Portland Farmers Market in Deering Oaks for a day of fundraising to benefit their Low-Income Access Program! Bid on items in the silent auction, sign up to be a Friend of the Market, purchase Market Goods, and draw at the kid’s table – all for a good cause from 7 am – 12 pm.

Maine’s own King of Comedy, Bob Marley, will be at OLS at 7 pm! Bob Marley has been taking simple woodsy humor and the word “wicked” across the nation and around the world for nearly two decades.

Eat local Maine oysters while sailing around Portland! Freshly shucked oysters from some of Sail Portland’s favorite farms. Shuck, sail and slurp your way to the most fun you’ll have in Portland from 6-8 pm.


Hang out at Bunker for Memorial Day weekend Sundaze! Eaux will be there slinging food and Scott Hajduk spinning funky vibes from 12 – 6 pm.

Gummy Bear Picnic, a big ole deck party for the whole family! There will be sour beer gummies made by Fore River and Deciduous as well as a children’s activity area and face painting – all for free. Starts at noon!

Head to Gritty’s for game night! Play Super Smash Bros & Mario Kart on the Nintendo Switch. Win prizes from Bull Moose starting at 3 pm. 21+ event!

Monday Memorial Day

Portland’s Memorial Day Parade will begin at 10:30 am at Longfellow Square and proceed down Congress Street ending at Monument Square. Join the City of Portland in commemorating the fallen.

Dress up like your favorite witch or wizard and head to Color Me Mine for a fun time painting owls, castles, luminaries, and other fun magical objects! There will be butter beer and light snacks from 4 – 6 pm.


Head to Soakology for a self-care workshop focusing on your head, neck, shoulders, and upper back. Learn how to alleviate discomfort and stiffness from 5 – 6:30 pm!


Gather your friends and head to Bayside Bowl for trivia night starting at 7 pm! There will be Bayside Bowl gift certificates and other prizes for the winners.


Monday’s are for Open Mic Night at Empire! 7 – 9:30 pm is music, poetry and more, and 9:30 – 11 pm is stand up comedy. 21+ event, there will be free pizza for comics!