Things to do in Portland

Wednesday, Dec 2

December Open Mic Night hosted by Thomas Clukey 🌱

One Longfellow Square

Join us for an Open Mic Night at One Longfellow Square for an evening of live music and community connection.

Thursday, Dec 3

KÖLSCH SERVICE — Belleflower Brewing

Belleflower Brewing Company

Enjoy a monthly Kölsch service with live music at Belleflower Brewing. Perfect for beer lovers looking for a communal atmosphere.

Thursday, Dec 3

The Year in Review Happy Hour: Producer Highlight

Grippy Tannins

Enjoy a special happy hour featuring standout wines at Grippy Tannins. Great for wine lovers and socializing.

Thursday, Dec 3

The Rainbow Affair

Live at Madrid's

Celebrate diversity at The Rainbow Affair with colorful performances in Portland. A lively evening for all.

Thursday, Dec 3

An Evening with Tom Rush Accompanied by Matt Nakoa and Brendan Cleary

One Longfellow Square

Enjoy an evening with Tom Rush, a pioneer of American music, at One Longfellow Square. A treat for folk music fans.

Friday, Dec 4

Jay Braggs Christmas In New Vaudeville

Live at Madrid's

Enjoy festive performances blending holiday cheer with vaudeville at Live at Madrid's in Portland.

Friday, Dec 4

GoldenOak with special guest Rachel Sumner & Traveling Light

One Longfellow Square

Experience a night of music with GoldenOak and special guest Rachel Sumner at One Longfellow Square.

Saturday, Dec 5

Pink Talking Fish

Live at Madrid's

Experience a unique blend of music by Pink Talking Fish at Live at Madrid's in Portland, ME.

Saturday, Dec 5

GoldenOak with special guest Eliza Edens

One Longfellow Square

Enjoy a night of music with GoldenOak and special guest Eliza Edens. Perfect for folk and acoustic music lovers.

Sunday, Dec 6

Maker's Market at Thompson's Point

Thompson's Point

Support local farms and artisans at the Maker's Market. Great for families and friends looking for unique crafts and treats.

Sunday, Dec 6

F1 WATCH PARTY: ABU DHABI GP

Three of Strong Spirits

Join fellow F1 fans for the Abu Dhabi GP watch party at Three of Strong Spirits. Enjoy food and drinks in a lively atmosphere.

Sunday, Dec 6

A Charlie Brown Christmas with The Heather Pierson Trio – 4PM SHOW

One Longfellow Square

Enjoy a festive performance of A Charlie Brown Christmas by The Heather Pierson Trio at One Longfellow Square.

Sunday, Dec 6

A Charlie Brown Christmas with The Heather Pierson Trio – 7PM SHOW

One Longfellow Square

Catch the 7 PM show of A Charlie Brown Christmas by The Heather Pierson Trio at One Longfellow Square.

Wednesday, Dec 9

Magic Tuber Stringband / Greg Jamie / Aaron Rosenblum

The Apohadion Theater

Enjoy a night of live music with Magic Tuber Stringband and guests at The Apohadion Theater. Great for folk music fans.

Thursday, Dec 10

The Year in Review Happy Hour: Spain and Italy

Grippy Tannins

Revisit favorite wines from Spain and Italy at this special happy hour event. Perfect for wine lovers looking to unwind.

Thursday, Dec 10

Portland Jazz Orchestra Holiday Show – Night 1

One Longfellow Square

Join the Portland Jazz Orchestra for their holiday show at One Longfellow Square. A festive event for jazz lovers.

Friday, Dec 11

Rigometrics - Rigsmas 2026

Live at Madrid's

Celebrate the season with Rigometrics - Rigsmas 2026 at Live at Madrid's, featuring live music and holiday cheer.

Friday, Dec 11

Portland Jazz Orchestra Holiday Show – Night 2

One Longfellow Square

Don't miss the second night of the Portland Jazz Orchestra's holiday show at One Longfellow Square. A treat for jazz fans.

Saturday, Dec 12

Maker's Market at Thompson's Point

Thompson's Point

Visit Thompson's Point for a vibrant Maker's Market featuring local farms and artisans. Perfect for families and friends looking for unique goods.

Saturday, Dec 12

Just Dance! Party

Three of Strong Spirits

Dance the night away at the Just Dance! Party with a lively DJ and drink specials at Three of Strong Spirits.

Saturday, Dec 12

Ugly Sweater Party with Bar Crawl USA

The Porthole Restaurant & Pub

Wear your best holiday sweater and enjoy drinks and laughter at the Ugly Sweater Party with Bar Crawl USA.

Saturday, Dec 12

Sparks the Rescue, Too Late The Hero, Broadwing, & Slim Jim Carrey

Live at Madrid's

Catch Sparks the Rescue and other bands at Live at Madrid's for an exciting night of music. Great for rock fans.

Sunday, Dec 13

S. Carey with special guest Hrishikesh Hirway

One Longfellow Square

Enjoy a live performance by S. Carey and special guest Hrishikesh Hirway at One Longfellow Square.

Monday, Dec 14

Lúnasa – An Irish Solstice Celebration: Night 1

One Longfellow Square

Join Lúnasa for an Irish solstice celebration featuring live music at One Longfellow Square.

Tuesday, Dec 15

Lúnasa – An Irish Solstice Celebration: Night 2

One Longfellow Square

Celebrate the Irish solstice with Lúnasa's live music performance at One Longfellow Square.

Thursday, Dec 17

The Year in Review Happy Hour: Burgundy

Grippy Tannins

Revisit memorable Burgundy wines at Grippy Tannins during this special happy hour event in Portland.

Thursday, Dec 17

The 17th Annual Ciclismo Classico Bike Travel Film Festival

One Longfellow Square

Enjoy inspiring travel films at the 17th Annual Ciclismo Classico Bike Travel Film Festival.

Friday, Dec 18

King Kyote

Live at Madrid's

Catch King Kyote for a vibrant live performance at Live at Madrid's. Ideal for music lovers looking for a lively night.

Friday, Dec 18

Jellyfish Rave

Flask Lounge

Join the Jellyfish Rave at Flask for a night of nautical fun with drink specials and costume encouragement. Ideal for party enthusiasts.

Friday, Dec 18

Springtide

One Longfellow Square

Experience a concert by Springtide featuring fiddle, cello, and guitar at One Longfellow Square.