Portland Holiday Events

Portland, ME Halloween Bar Crawl

Portland 25 Oct 2025

Annual Fiera Di Natale Christmas Craft Fair & Italian Bake Sale at the Italian Heritage Center

40 Westland Ave, Portland, ME, United States, Maine 04102 1 Nov 2025

Portland, ME Day of The Dead Bar Crawl - Dia De Muertos

Portland 1 Nov 2025

WPOR Jingle Jam 2025

Aura 5 Dec 2025

Bailey's Mistake at the MIHC!

34 Gray St, Portland, ME, United States, Maine 04102 13 Dec 2025

Portland, ME Ugly Sweater Bar Crawl

Portland 20 Dec 2025

Portland Ugly Sweater Bar Crawl: 8th Annual

Registration: Fore Play Bar 13 Dec 2025

Maine Irish Celtic Fair

34 Gray St, Portland, ME, United States, Maine 04102 8 Nov 2025

Portland, ME St. Patrick's Day Bar Crawl

Porttown Public House 14 Mar 2026

2025 Portland, ME Thanksgiving Eve Bar Crawl

Mathew's 26 Nov 2025

Windborne: To Warm the Winter Hearth at OLS

181 State Street, Suite 201, Portland, ME, United States, Maine 04101 14 Nov 2025

Grippy Tannins x Embody — December Holiday Event

Grippy Tannins 1 Dec 2025

Spending Christmas with Alicia Witt

181 State Street, Suite 201, Portland, ME, United States, Maine 04101 10 Dec 2025

Winter Wreath Making with Mare Brook Farm at Blind Tiger Guest House

Blind Tiger 6 Dec 2025

Scheherazade at Merrill Auditorium

Merrill Auditorium 16 Nov 2025

Rosemont Artist Guild Holiday Market

Breakwater School 15 Nov 2025

Raise a Glass: MJM Logo Launch Party!

Maine Jewish Museum 23 Oct 2025

Zlateh’s Hanukkah Party: A Goat, a Garden & Great Fun

Maine Jewish Museum 7 Dec 2025

Portland Jazz Orchestra Holiday Show - NIGHT 2

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

Home Fur The Howlidays | Pittie Posse Holiday Market

The Bark Yard 7 Dec 2025

Winter Wreath Making with Mare Brook Farm at Blind Tiger Guest House

Blind Tiger 5 Dec 2025

Christmas with Kennerley

Merrill Auditorium 23 Dec 2025

Choir! Choir! Choir! Presents Un-Silent Night

State Theatre, Portland, Maine 2 Dec 2025

Maine Public Holiday Paint and Sip Night

Rising Tide Brewing Company 7 Dec 2025

St. Lucia’s Day Procession with Merulae

10 Mayo St, Portland, ME, United States, Maine 04101 6 Dec 2025

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

181 State Street, Suite 201, Portland, ME, United States, Maine 04101 7 Dec 2025

Maine Irish Reads “The Sea” by John Banville

34 Gray St, Portland, ME, United States, Maine 04102 13 Nov 2025

Portland Jazz Orchestra Holiday Show - NIGHT 1

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

Crafternoons at coworkHERS - Wrappy Hour

coworkHERS LLC 19 Dec 2025

Rock My Soul

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

SEASON’S GREETINGS

FLASK LOUNGE 3 Dec 2025

Portland to Hampton Getaway | Last hurrah before the holidays!

Old Port in Portland, ME 14 Nov 2025

Portland Supper Club - Farm to Table Dinner Series

Blind Tiger Portland – Danforth Street 15 Aug 2025

Portland Symphony Orchestra - Magic of Christmas at Merrill Auditorium

Merrill Auditorium 12 Dec 2025

Another Evening at Dave's Sauna - Holiday HiJinXXX

76 Congress St, Portland, ME 04101-3617, United States 6 Dec 2025

Choir! Choir! Choir! - Un-Silent Night: An Epic Holiday Sing Along at State Theatre Portland

State Theatre Portland 2 Dec 2025