Portland Holiday Events

Portland ME Halloween Bar Crawl 2026

Mathew's 31 Oct 2026

Portland, ME Halloween Bar Crawl

Mathew's 24 Oct 2026

Maker's Market at Thompson's Point!

Thompsons Point Rd, Portland, ME 04102, United States 25 Oct 2026

Portland Official Thanksgiving Eve Bar Crawl 2026

Downtown Portland 25 Nov 2026

Whimsy Workshop: Gothic Halloween Wreaths

Terrarium 16 Oct 2026

Portland Symphony Orchestra - Magic of Christmas at Merrill Auditorium

Merrill Auditorium 11 Dec 2026

Portland SantaCon Bar Crawl 2026

Mathew's 12 Dec 2026

Strut Krampus: Miss Ma'am She + Portland's Filfiest Holiday Party

SPACE 12 Dec 2026

Sea Spray @ Holiday Maker’s Market ‘26

Thompson's Point 6 Dec 2026

Cheese Board Building

Sissle & Daughters Cheesemongers and Grocers 14 Nov 2026

Becky Robinson's Holiday Spectacular at State Theatre Portland

State Theatre Portland 6 Dec 2026

Gary Hoey - Ho Ho Hoey's Rockin' Holiday Show at Portland HOME House of Music and Events

Portland HOME House of Music and Events 5 Dec 2026

The Christmas Bar Crawll - Portland, ME

Fore Play Sports Pub 19 Dec 2026

Candlelight: Christmas Classics

Stevens Square Theater 20 Dec 2026

Harvest Craft Show

Stevens Square Community Center 24 Oct 2026

HOLIDAY HI-JINXXX "ANOTHER EVENING AT DAVE'S SAUNA"

The Hill Arts ME 4 Dec 2026

Wreath Decorating

Blind Tiger Portland – Carleton Street 6 Dec 2026

Two Minutes Out - Live at Andy’s - HOLIDAY SPECIAL

Andy's Old Port Pub 19 Dec 2026

Annual Celtic Fair 2026

34 Gray St, Portland, ME, United States, Maine 04102 14 Nov 2026

Benefit Holiday Wreath Workshop! 🎄

The Point Community Center 23 Nov 2026

Downeasters 2026 Holiday Show

Crewe Center for the Arts 17 Dec 2026

Portland Ugly Sweater Bar Crawl: 9th Annual

Registration: Fore Play Bar 12 Dec 2026

AFTER DARK

155 Riverside St Suite D, Portland, ME 26 Dec 2026

The Women Who Raise Us: Stitching Together Stories of Motherhood

Mechanics' Hall 12 Nov 2026