Holiday events in Portland

• Sat, 20 Dec, 2025 - 04:00 PM

  Portland, ME Ugly Sweater Bar Crawl

  Portland

  Free
• Fri, 05 Dec, 2025 - 06:00 PM

  Sip & Paint: Holiday Wine Glass Edition

  219 Anderson Street, Suite 2, Portland, ME, United States, Maine 04101

  25+ Interested
• Sat, 13 Dec, 2025 - 04:00 PM

  Portland Ugly Sweater Bar Crawl: 8th Annual

  Registration: Fore Play Bar

  USD 24
• Fri, 19 Dec, 2025 - 08:00 PM

  Adult Story Time with THEM Burlesque | Smutty Holidays

  Novel

  USD 18
• Sun, 07 Dec, 2025 - 06:00 PM

  Maine Public Holiday Paint and Sip Night

  Rising Tide Brewing Company

  USD 50
• Sun, 07 Dec, 2025 - 10:00 AM

  Home Fur The Howlidays | Pittie Posse Holiday Market

  The Bark Yard

  244+ Interested
• Thu, 04 Dec, 2025 - 06:00 PM

  The Portland Girls Club Holiday Party

  Ballast

  USD 40
• Fri, 12 Dec, 2025 - 04:30 PM

  MHS Members' Holiday Party!

  489 Congress St, Portland, ME, United States, Maine 04101

  12+ Interested
• Sat, 06 Dec, 2025 - 02:00 PM

  QMM Holiday Market

  519 Congress St, Portland, ME, United States, Maine 04101

  4+ Interested
• Sat, 06 Dec, 2025 - 02:00 PM

  Oyster Ornament Decoupage with Lady Shuckers at Angoor Wine Bar!

  Angoor Wine Bar

  USD 45
• Sat, 06 Dec, 2025 - 02:00 PM

  St. Lucia’s Day Procession with Merulae

  10 Mayo St, Portland, ME, United States, Maine 04101

  9+ Interested
• Fri, 19 Dec, 2025 - 03:00 PM

  Crafternoons at coworkHERS - Wrappy Hour

  coworkHERS LLC

  USD 13
• Sat, 13 Dec, 2025 - 08:00 PM

  STRUT Krampus!

  SPACE

  USD 34
• Sat, 13 Dec, 2025 - 12:00 PM

  Fete Holiday Day Market at Toad & Co Portland (2 day market)

  Toad&Co Portland
• Tue, 02 Dec, 2025 - 07:30 PM

  Choir! Choir! Choir! Presents Un-Silent Night

  State Theatre, Portland, Maine

  130+ Interested