Holiday events in Portland, ME

Friday, Oct 30

Orange Bike Brewing Co. — Orange Bike Night Before Halloween Party

Orange Bike Brewing Company

Friday, Oct 30

All Hallows-Eve Costume Dance Party

Blue Portland Maine

Dress up and dance at the All Hallows-Eve Costume Dance Party at Blue Portland Maine. A fun night for costume lovers and dance enthusiasts.

Saturday, Oct 31

the Casket's 2026 Hallow's Eve Monster Mash

Aura

Rise from the grave and start your halloween weekend right with the Casket's Hallow's Eve Monster Mash! KILLER ENTERTAINMENT & HUGE PRIZES!

Saturday, Oct 31

Halloween

Pizzaiolo

Bring your best costume and join us on Halloween!

Saturday, Oct 31

After Dark Halloween Party

The Porthole Restaurant & Pub

Saturday, Oct 31

After Dark Halloween Party

The Porthole Restaurant & Pub

Saturday, Oct 31

Pumpkinhead Halloween Rave: Featuring The Hive & Bassix

Shipyard Brewing Company

Halloween night rave, haunted house decor, costume contest, and Pumpkinhead celebration at the Shipyard Tasting Room.

Sunday, Nov 1

HELLEFLOWER!!! Halloween Burly & Drag @ Belleflower Brewing

Belleflower Brewing Company

Port City Peep Show returns to Belleflower Brewing on Halloween night--after a day of spicy treats from Iron Clad Eats!

Sunday, Nov 1

Halloween with Jelly Sauce band

Flask Lounge

Enjoy a night of live music with Jelly Sauce and DJ Joseph Ghost at Flask Lounge. Perfect for Halloween fun.

Sunday, Nov 1

HALLOWEEN with Future Mailmen and Spooky Karaoke

Blue Portland Maine

Celebrate Halloween at BPM with live music from Future Mailmen and a spooky karaoke session.

Sunday, Nov 1

All Hallows’ Eve: Spooky Tunes, Songs and Tales from Scotland

One Longfellow Square

<p>.stk-vpew5v7 {height:25px !important;} Doors open an hour before showtime. .stk-j1gcadx {height:25px !important;} Joined by guitarist Conor Hearn, mandolinist Ethan Setiawan and cellist Brendan Hearn, and special guests, Louise Bichan presents […]</p>\n

Sunday, Nov 1

A Very Jerry Halloween with Rose Alley (Jerry Garcia Band Tribute)

Bayside Bowl

A Very Jerry Halloween with Rose Alley (Jerry Garcia Band Tribute) at Bayside Bowl | all-ages

Saturday, Dec 5

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.

Sunday, Dec 6

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

One Longfellow Square

<p>.stk-en80zyx {height:25px !important;} Doors open an hour before showtime. THIS IS FOR THE 4PM SHOW .stk-jshi31c {height:25px !important;} Heather Pierson is a nationally touring singer/songwriter, pianist, community song leader, educator, and poet […]</p>\n

Monday, Dec 7

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

One Longfellow Square

<p>.stk-fdicvnr {height:25px !important;} Doors open an hour before showtime. THIS IS FOR THE 7PM SHOW .stk-fr96wmn {height:25px !important;} Heather Pierson is a nationally touring singer/songwriter, pianist, community song leader, educator, and poet […]</p>\n

Friday, Dec 11

Portland Jazz Orchestra Holiday Show – Night 1

One Longfellow Square

<p>THIS IS FOR NIGHT 1 .stk-t9e9cy0 {height:25px !important;} Doors open an hour before showtime. .stk-rg3elb2 {height:25px !important;} Portland’s own 17-piece Portland Jazz Orchestra brings their annual holiday tradition back to One Longfellow […]</p>\n

Saturday, Dec 12

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.

Saturday, Dec 12

Portland Jazz Orchestra Holiday Show – Night 2

One Longfellow Square

<p>THIS IS FOR NIGHT 2 .stk-nu7igc6 {height:25px !important;} Doors open an hour before showtime. .stk-qnvmb7c {height:25px !important;} Portland’s own 17-piece Portland Jazz Orchestra brings their annual holiday tradition back to One Longfellow […]</p>\n

Saturday, Dec 12

Ugly Sweater Party with Bar Crawl USA

The Porthole Restaurant & Pub

Sunday, Dec 13

Ugly Sweater Party with Bar Crawl USA

The Porthole Restaurant & Pub

Tuesday, Dec 15

Lúnasa – An Irish Solstice Celebration: Night 1

One Longfellow Square

<p>THIS IS FOR NIGHT 1 .stk-rbxu1o7 {height:25px !important;} Doors open an hour before showtime. .stk-qz3rwro {height:25px !important;} Named for an ancient Celtic harvest festival in honour of the Irish god […]</p>\n

Wednesday, Dec 16

Lúnasa – An Irish Solstice Celebration: Night 2

One Longfellow Square

<p>THIS IS FOR NIGHT 2 .stk-blvcj7d {height:25px !important;} Doors open an hour before showtime. .stk-5qi7kah {height:25px !important;} Named for an ancient Celtic harvest festival in honour of the Irish god […]</p>\n

Sunday, Dec 20

Julia Haven Holiday Concert

One Longfellow Square

<p>.stk-j4fcjpg {height:25px !important;} Doors open an hour before showtime. .stk-ufbamdp {height:25px !important;} Julia Haven (formerly Julia Gagnon), an American Idol Season 22 Top 7 finalist, brings her powerful voice and […]</p>\n

Sunday, Dec 20

Windborne: Music of Midwinter

One Longfellow Square

<p>.stk-8dayxsq {height:25px !important;} Doors open an hour before showtime. .stk-93xp04w {height:25px !important;} A joyful and heartfelt celebration of song, Windborne’s lush vocals and unique arrangements bring light to a dark […]</p>\n

Thursday, Dec 31

New Year’s Eve with Hello Newman & After Dark

The Porthole Restaurant & Pub

Thursday, Dec 31

New Year's Eve

Pizzaiolo

Celebrate the New Year with us and join us on New Year's Eve!

Thursday, Dec 31

New Year’s Eve with Hello Newman & After Dark

The Porthole Restaurant & Pub

Friday, Jan 1

NYE | THE AWESOME (21+)

Bayside Bowl

Maine's beloved 80s band, The AWESOME, comprised of members from some of Maine's most prolific acts, play NYE at Bayside Bowl

Friday, Jan 1

A Havana New Year’s Eve Bash with Primo Cubano!

One Longfellow Square

<p>.stk-zjdvreh {height:25px !important;} Doors open an hour before showtime. .stk-t1e6eyt {height:25px !important;} Where Primo Cubano goes, people dance. For the better of two decades, they have been bringing the infectious […]</p>\n