Portland Boos & Booze Halloween Bar Crawl: 2nd Annual, by Bar Crawl USA Sat, 24 Oct at 04:00 pm Fore Play Sports Pub USD 18 TO 20 FITNESS
Batson River Drag Brunch: ROCKY HORROR Sun, 25 Oct at 10:30 am Batson River Brewing & Distilling -- Portland USD 23 FITNESS
HALLOWEEN: AFTER DARK | Night Frights LA (Portland, ME) Fri, 23 Oct at 05:00 pm Bissell Brothers USD 0 TO 29 FITNESS
2nd Annual Cookie Fest at The Messy Cookie 🍪 Sat, 17 Oct at 10:00 am 1190 Forest Ave, Portland, ME FESTIVALS
Pumpkinhead Halloween Rave: Featuring The Hive & Bassix Sat, 31 Oct at 07:00 pm Shipyard Brewing Company USD 0 TO 25 FITNESS
Maker's Market at Thompson's Point! Sun, 25 Oct at 10:00 am Thompsons Point Rd, Portland, ME 04102, United States
5k Fun Run at Allagash Brewing | 2026 New England Brewery Running Series Sat, 24 Oct at 11:00 am Allagash Brewing Company USD 42 TO 63 WORKSHOPS
Sister Sparrow & The Dirty Birds w/s/g Savoir Faire live at Bayside Bowl Fri, 16 Oct at 08:00 pm Bayside Bowl USD 29 FITNESS
SOS x Angoor Wine Bar: Single Ladies' Bachelorette Party Sun, 18 Oct at 04:30 pm Angoor Wine Bar USD 34 FITNESS
A Day Retreat: Community Gathering of Ceremony, Culture, Food & Belonging Sun, 18 Oct at 10:00 am Good Medicine Collective USD 173 TO 215 FITNESS
Weird Phishes | Radiohead Through the Lens of Phish live at Bayside Bowl Sat, 24 Oct at 08:00 pm Bayside Bowl USD 18 FITNESS
Funk Jerry: Funking Up The Music Of Jerry Garcia Fri, 06 Nov at 07:00 pm 49 Washington Avenue, Portland, ME, United States, Maine 04101 MUSIC
Ronald McDonald House Maine Gala Presented by Maine Community Bank Fri, 13 Nov at 06:00 pm Thompson's Point MUSIC
Portland Official Thanksgiving Eve Bar Crawl 2026 Wed, 25 Nov at 08:00 pm Downtown Portland USD 0 TO 13 FITNESS
Feud Night at Riverton Station in Portland! Sat, 24 Jan at 06:00 pm Riverton Station Pizza, Bar & Grill FREE FITNESS
Grump & Sunshine Bookshop Halloween Party Fri, 30 Oct at 07:00 pm 40 Free St, Portland, ME, United States, Maine 04101 HEALTH-WELLNESS
Portland, ME Murder Mystery: Solve the case! Sun, 01 Nov at 12:00 am 1 Temple St, Portland, ME 04101, USA USD 10 GHOST-HUNTS
The Red Eye Flight Crew Halloween Bash at PHOME Sat, 31 Oct at 08:00 pm 25 Temple St, Portland, ME, United States, Maine 04101
Portland Symphony Orchestra - The Magic of Christmas at Merrill Auditorium Sat, 12 Dec Merrill Auditorium MUSIC
Milk St. & Alma June & The Persian Cats live at Bayside Bowl | all-ages Sat, 17 Oct at 08:00 pm Bayside Bowl USD 18 FITNESS
Greater Portland Branch Halloween Party Fri, 30 Oct at 05:00 pm 70 Forest Ave, Portland, ME 04101-2813, United States HALLOWEEN-PARTIES
STUFF'D a Thanksgiving Eve Dance Party with Cherry Lemonade & Friends Wed, 25 Nov at 08:00 pm Aura MUSIC
Daikaiju Attacks The Monster’s Ball w/ Greenbriar, Tarots, Nightbirds Sat, 17 Oct at 07:00 pm Veterans of Foreign Wars USD 18 FITNESS
Strut Krampus: Miss Ma'am She + Portland's Filfiest Holiday Party Sat, 12 Dec at 08:00 pm SPACE USD 36 TO 45 HOLIDAY
Crafts & Drafts: Macramé Plant Hangers at Definitive Brewing Tue, 13 Oct at 06:00 pm Definitive Brewing Company USD 34 TO 66 WORKSHOPS
BINGO - Blind Tiger Guest House! Sun, 01 Nov at 12:00 pm Blind Tiger Portland – Danforth Street USD 29 FITNESS
Daily Bread - Vanishing Point Tour w/ Steller & Motifv Thu, 10 Dec at 08:00 pm State Theatre, Portland, Maine ART
Cheese Board Building Sat, 14 Nov at 07:00 pm Sissle & Daughters Cheesemongers and Grocers USD 109 FITNESS
New Year’s Eve at Grace | Portland’s Elegant NYE Celebration Thu, 31 Dec at 08:00 pm 15 Chestnut St USD 55 TO 1,069 FITNESS
The Christmas Bar Crawll - Portland, ME Sat, 19 Dec at 04:00 pm Fore Play Sports Pub USD 13 TO 18 FITNESS
Candlelight: Christmas Classics Sun, 20 Dec at 08:30 pm Stevens Square Theater USD 22 TO 42 CANDLELIGHT-CONCERTS
Reading Royals at Maine Mariners at Cross Insurance Arena Sat, 19 Dec at 06:00 pm Cross Insurance Arena TRIPS-ADVENTURES
Trunk or Treat @ Spare Time Portland Sat, 24 Oct at 11:00 am 867 Riverside St, Portland, ME, United States, Maine 04103 TRUNK-OR-TREAT
Crushville Presents Stevie Wonder vs. Earth, Wind & Fire Thu, 05 Nov at 08:00 pm 25 Temple St, Portland, ME, United States, Maine 04101 MUSIC
The Meadow We Weave: The World's First Seagrass Ceilidh Sat, 21 Nov at 05:30 pm State Street Church USD 0 TO 150 FITNESS
Limited Edition Rivals Replica Game Ball From Spalding® Thu, 11 Feb at 07:00 pm Cross Insurance Arena MISCELLANEOUS
Fifth Annual Great Big Maine Challah Bake Sun, 15 Nov at 01:00 pm 1342 Congress Street, Portland, ME, United States, Maine 04102 NONPROFIT
Walk & Roll! Sun, 11 Oct at 01:00 pm High and Congress Streets, Portland, ME, United States, Maine 04101
Stolen Mojo and Checkered Past New Year's Eve Bash at The Double Tree! Thu, 31 Dec at 07:30 pm DoubleTree by Hilton Hotel Portland, ME USD 61 FITNESS
SALSA NIGHT | with DANZA LATINA | SALSA LESSON & LATIN DANCE PARTY Fri, 06 Nov at 07:00 pm Three of Strong Spirits DANCE