Portland Holiday Events

Lowry’s Lodge Presents: Holiday Open Reading

Maine Jewish Museum 14 Dec 2025

Portland, ME Ugly Sweater Bar Crawl

Portland 20 Dec 2025

Monument Square Tree Lighting

Monument Square 28 Nov 2025

Adeline Spa Open House

Adeline Wellness Spa 13 Nov 2025

Holly Jolly Follies - presented by Vivid Motion Dance

The Hill Arts ME 12 Dec 2025

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

Blind Tiger 6 Dec 2025

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

Blind Tiger 5 Dec 2025

Home Fur The Howlidays | Pittie Posse Holiday Market

The Bark Yard 7 Dec 2025

2025 Portland, ME Thanksgiving Eve Bar Crawl

Mathew's 26 Nov 2025

International Artisan Fair

40 Walch Drive, Portland, ME, United States, Maine 04103 5 Dec 2025

Cobblestone Quilters Holiday Market

Woodfords Club 15 Nov 2025

Windborne: To Warm the Winter Hearth at OLS

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

Spending Christmas with Alicia Witt

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

Portland, ME St. Patrick's Day Bar Crawl

Porttown Public House 14 Mar 2026

Comfort and Joy: Christmas in Olde New England Tours of the Wadsworth-Longfellow House

489 Congress St, Portland, ME, United States, Maine 04101 29 Nov 2025

DIY Holiday Cork Ornaments & Mod Podge Votives - Portland Crafting Girlies

Hardshore Distilling Company 9 Dec 2025

Grippy Tannins x Embody — December Holiday Event

Grippy Tannins 1 Dec 2025

Rosemont Artist Guild Holiday Market

Breakwater School 15 Nov 2025

Portland Ugly Sweater Bar Crawl: 8th Annual

Registration: Fore Play Bar 13 Dec 2025

Christmas Hangover Party with Hello Newman 🎅

Portland House of Music and Events 26 Dec 2025

Choir! Choir! Choir! Presents Un-Silent Night

State Theatre, Portland, Maine 2 Dec 2025

Portland Jazz Orchestra Holiday Show - NIGHT 2

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

Christmas with Kennerley

Merrill Auditorium 23 Dec 2025

Wayside Thanksgiving Volunteer Shifts 2025

Wayside Food Programs 24 Nov 2025

A Colonial Christmas at Tate House Museum

Tate House Museum 13 Dec 2025

Scheherazade at Merrill Auditorium

Merrill Auditorium 16 Nov 2025

Maine Public Holiday Paint and Sip Night

Rising Tide Brewing Company 7 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

RWS Holiday Sale

Running With Scissors Artist Studios & Community 12 Dec 2025

St. Lucia’s Day Procession with Merulae

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

Maine Irish Reads “The Sea” by John Banville

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

2025 Dec’ the Walls - Gingerbread House Decorating

Hilton Garden Inn Portland Downtown Waterfront 14 Dec 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

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

Maine Jewish Museum 7 Dec 2025

Rock My Soul

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

Portland to Hampton Getaway | Last hurrah before the holidays!

Old Port in Portland, ME 14 Nov 2025

Georgia Peach Truck - South Portland, ME @ Broadway Gardens

1640 Broadway, South Portland, ME 04106-3424, United States 4 Dec 2025

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

Cross Insurance Arena 20 Dec 2025

SEASON’S GREETINGS

FLASK LOUNGE 3 Dec 2025

Mini Makers – Kids’ Winter Workshop!

Halo At The Point - Thompson's Point 5 Dec 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