Portland Holiday Events

Paul Winter's Winter Solstice Celebration

Cathedral Church of St. Luke 17 Dec 2025

Symphony & Spirits: Magic of Christmas

Arcadia - Portland, Me 19 Dec 2025

Parents Night Out!

333 Clarks Pond Parkway, South Portland, ME, United States, Maine 04106 19 Dec 2025

AURA NYE 2025 at Aura - Portland

Aura - Portland 31 Dec 2025

Portland, ME Ugly Sweater Bar Crawl

Portland 20 Dec 2025

Portland, ME St. Patrick's Day Bar Crawl

Porttown Public House 14 Mar 2026

Flow Sanctuary

Good Medicine Collective 19 Dec 2025

Crafternoons at coworkHERS - Wrappy Hour

coworkHERS LLC 19 Dec 2025

Giftwrapped: Holiday Toy Drive Rave With The Hive

Three Dollar Deweys 20 Dec 2025

14th Annual EXPERIMENTAL SANTA

The Apohadion Theater 20 Dec 2025

Christmas Hangover Party with Hello Newman 🎅

Portland House of Music and Events 26 Dec 2025

A Hometown Holiday with 12/OC and Friends at Cross Insurance Arena

Cross Insurance Arena 20 Dec 2025

Portland Jazz Orchestra Holiday Show - NIGHT 2

181 State Street, Suite 201, Portland, ME, United States, Maine 04101 19 Dec 2025

Rock My Soul

181 State Street, Suite 201, Portland, ME, United States, Maine 04101 21 Dec 2025

Holiday Charm Bracelet Brunch

Blind Tiger Portland – Danforth Street 21 Dec 2025

Adult Story Time with THEM Burlesque | Smutty Holidays

Novel 19 Dec 2025

BlitzN'Spritz - An Old Port Winter Shopping Event

Exchange Street 18 Jan 2026

GRC Holiday Trial

18 Ashmont st, Portland, ME, United States, Maine 04103 21 Dec 2025

Winter Bazaar Food & Gift Markets

95 Darling Ave., South Portland, ME, United States, Maine 04106 18 Dec 2025

Santarchy ~ Portland Maine

Portland Maine 20 Dec 2025

Portland Jazz Orchestra Holiday Show - NIGHT 1

181 State Street, Suite 201, Portland, ME, United States, Maine 04101 18 Dec 2025

Santa is coming to Big Moose Harley-Davidson!

Big Moose Harley-Davidson 20 Dec 2025

Christmas with Kennerley

Merrill Auditorium 23 Dec 2025

2026 New Year Spectacular

Holiday Inn Portland-by the Bay 17 Jan 2026

Mini Makers – Kids’ Winter Workshop!

Halo At The Point - Thompson's Point 5 Dec 2025

UNO Portland Kids Event - Holiday Cookie Decorating

280 Maine Mall Rd Maine Mall, South Portland, ME 04106 16 Dec 2025

Sluts In Sweaters: A Holigay Drag Show

Novel 22 Dec 2025

Portland Symphony Orchestra - Magic of Christmas at Merrill Auditorium

Merrill Auditorium 12 Dec 2025