Portland Holiday Events

Portland Official Thanksgiving Eve Bar Crawl 2026

Mathew's 25 Nov 2026

Portland SantaCon Bar Crawl 2026

Mathew's 12 Dec 2026

Portland Symphony Orchestra - Magic of Christmas at Merrill Auditorium

Merrill Auditorium 11 Dec 2026

STRUT KRAMPUS feat. Miss Ma'am She — Portland's Filthiest Holiday Party

SPACE 12 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

Sea Spray @ Holiday Maker’s Market ‘26

Thompson's Point 6 Dec 2026

The Christmas Bar Crawll - Portland, ME

Fore Play Sports Pub 19 Dec 2026

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

The Hill Arts ME 4 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

Candlelight: Christmas Classics

Stevens Square Theater 20 Dec 2026

Cozy Girl Social

Coffee By Design 7 Nov 2026

2026 IHC Annual Craft Fair & Bake Sale Italian Heritage Center

40 Westland Ave, Portland, ME, United States, Maine 04102 7 Nov 2026

Golden Goddesses: Celebrating 50 Drag Brunches!

Batson River Brewing & Distilling -- Portland 29 Nov 2026

Wreath Decorating

Blind Tiger Portland – Carleton Street 5 Dec 2026

First Day of 2027 Ticket Sales & Hadlock Field Yard Sale

271 Park Ave, Portland, ME, United States, Maine 04102 7 Nov 2026

Annual Celtic Fair 2026

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

Adeline Wellness Spa Open House

Adeline Wellness Spa 19 Nov 2026

Whipped & Frosted

Grump & Sunshine Bookshop 4 Dec 2026

Fused Glass: Layers

The Photo Kitchen 9 Nov 2026

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

Andy's Old Port Pub 19 Dec 2026

Home Free - Coming Home For The Holidays

State Theatre, Portland, Maine 13 Dec 2026

Portland, ME Christmas Bar Crawl 2026

Fore Play Sports Pub 19 Dec 2026

Holiday Fair & Luncheon

159 State Street, PO Box 4037, Portland, ME, United States, Maine 04101 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

Holiday Open House at Cosmetic Enhancement Center of New England

1945 Congress Street, Portland, ME, United States, Maine 04102 18 Nov 2026

Bid Tree Lighting

Broadway/Main Corner 25 Nov 2026

St. Lucia's Day Procession

Mayo Street Arts 12 Dec 2026

Bizarre Bazaar

515 Woodford St, Portland, ME 04103-2439, United States 12 Dec 2026

2026-12-20 Maine Pops Small Ensembles Holiday Concert

Hope Gate Way 20 Dec 2026

ChoralART Holiday Singalong

Portland Conservatory of Music 12 Dec 2026

Home for the Holidays

Portland Conservatory of Music 26 Dec 2026

2026-12-21 Clarinet Chromatics Holiday Performance at Maine Mall

Maine Mall, South Portland, ME 04106, United States 21 Dec 2026

Plush & Holiday Inn By The Bay NYE 2027! Portland's Premiere NYE Party!

88 Spring St 31 Dec 2026

Christmas with Kennerley

Merrill Auditorium 22 Dec 2026

PTA Meeting in the Art Room

180 Wescott Rd, South Portland, ME, United States, Maine 04106 12 Nov 2026

2027 New Year Spectacular

Holiday Inn Portland-by the Bay 16 Jan 2027

Portland Ugly Sweater Bar Crawl: 9th Annual

Registration: Fore Play Bar 12 Dec 2026

2026-12-14 Harbor Brass Quintet Holiday Performance at Portland International Jetport

Portland International Jetport-Maine 14 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

Portland Art Gallery December Opening: Evergreen

Portland Art Gallery 3 Dec 2026

2026 THE Gala to Benefit Toys For Tots

Grace Wedding Venue & Event Center 4 Dec 2026

MARR 10 Year Anniversary Gala Night

Holiday Inn Portland-by the Bay 23 Jan 2027

Sea Spray @ Holiday Specialty Foods Market ‘26

Halo At The Point 13 Dec 2026

Yule Be Groovin' North with The Rockingham Groove and Maine Ballroom Dance

Woodfords Club 5 Dec 2026

2026-12-12 Harbor Brass Quintet Holiday Performance at Portland Jetport

Portland International Jetport-Maine 12 Dec 2026