The Weekend Guide for December 20th-22nd | Portland Old Port

The Weekend Guide for December 20th-22nd

Portland, Maine is hopping this weekend! Carol in Deering Oaks, attend an ugly sweater dance party, grab tickets to one of the many shows, or give at Boom Santa-Lanta. There’s no shortage of fun events!


The Maine Oyster Company is hosting Boom Santa-Lanta from 2-6pm! Santa will be giving a gift to any child in need. There will also be oyster ornament decorating and hot chocolate! Their goal is to raise $1,000 to buy winter clothes and gifts for kids of the community!

Attend Portland’s Annual Homeless Persons’ Memorial Vigil in Monument Square. A candlelight procession will begin at the Preble Street Resource Center at 4:30pm and end in Monument Square where a ceremony for the deceased members of our community will take place. All are welcome.

The International Open Mic Night will be at Mayo Street Arts from 7-9pm. Advance registration is strongly recommended. Tickets are $10 in advance and $15 day of. However, there is a sliding scale for no and low income. No one is turned away, all are welcome! 

The Holiday GQB (Guerilla Queer Bar) will take place at Three Dollar Dewey’s. Rainbow heart stickers will be available to make the LGBTQ+ community visible.

Grab a ticket to Disney on Ice at the Cross Insurance Arena! Tickets range from $15-$75 and the show starts at 7pm! Costumes encouraged for children 14 and under!

Listen to Gumboots- A Tribute to Paul Simon at the Portland House of Music and Events! Tickets are $10 in advance and $15 day of. The doors open at 7pm and the music starts at 8pm. This is a 21+ event so don’t forget your ID!


Stop by Fork Food Lab for a Holiday Market from 11am-2pm! Admission is free, RSVP on their Facebook! 

The 8th annual Experimental Santa will be at The Apohadion Theater from 8-11pm. It’s bigger and better than ever with lights, sound, video, and special guests!

Check out Jingle Buzz Jingle Buzz Jingle Buzz Rocks at The Tail End from 8pm-1am. There will be drink specials as well as a costume contest with prizes for first, second, and third place!

Throw on your worst holiday garb and attend An Ugly Sweater Party-Let’s Get Nogged at the Whiskey Barrel! There will be a prize for the worst dressed! This event starts at 9pm and admission is free. This is a 21+ event.


Grab tickets to Motown for Kids Holiday Celebration at the Port City Music Hall hosted by The Rock and Roll Playhouse! Tickets are $15 and children under 1 year are free. The doors open at 11am and the show starts at 11:30am. This is an all ages event!

Attend the Live Holiday Card Print Making Party at Rising Tide Brewing Company from 12-7pm! Learn how to make cards from Julia Starr and get a unique holiday card!

Deering Oaks Caroling will be held from 3:30-5pm, so stop by for a song! The community will be gathering at Rwanda Bean at 3:30pm and the caroling will start at 4pm! 

Grab a ticket to Ian Stuart’s Naughty List a One Man Holiday Show at Portland House of Music and Events. Doors open at 6pm and the comedy show starts at 7pm. Tickets are $10 in advance and $15 day of. This is a 21+ event.