Holiday events in Annapolis

• Sun, 07 Dec, 2025 - 10:00 AM

  Nutcracker Tea 2025

  DoubleTree by Hilton Hotel Annapolis

  26+ Interested
• Sat, 13 Dec, 2025 - 05:00 PM

  Annapolis Holiday of Lights Boat Parade

  680 Americana Dr

  USD 107
• Thu, 04 Dec, 2025 - 06:30 PM

  Peter White, Mindi Abair, Vincent Ingala in Annapolis

  Rams Head On Stage
• Thu, 11 Dec, 2025 - 06:00 PM

  Midnight Madness West Street Artisan Holiday Market

  60 West St, Annapolis, MD 21401-2434, United States

  1509+ Interested
• Sat, 20 Dec, 2025 - 07:00 PM

  Jon McLaughlin and Friends: Home For The Holidays

  Rams Head On Stage
• Sat, 20 Dec, 2025 - 07:00 PM

  Happy Holidays Drag Brunch

  Rams Head On Stage
• Sat, 06 Dec, 2025 - 06:00 PM

  SOD-O Holiday Party

  Acqua al 2 - Annapolis

  Free
• Sun, 07 Dec, 2025 - 06:00 PM

  2025 Bike Doctor Holiday Lights Ride

  Safe Harbor Podickory Point

  11+ Interested
• Sat, 20 Dec, 2025 - 12:00 PM

  A SQRRL! Holiday (Matinee)

  Rams Head On Stage
• Sat, 13 Dec, 2025 - 11:00 AM

  Annapolis Holiday Market 2025

  St. John's College

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

  2025 FRA 24 Holiday Party

  Fleet Reserve Club Of Annapolis

  USD 66
• Sat, 06 Dec, 2025 - 02:00 PM

  A Colonial Yuletide

  186 Prince George St, Annapolis, MD 21401-1724, United States

  91+ Interested
• Fri, 19 Dec, 2025 - 07:30 PM

  Holiday Pops at Maryland Hall

  Maryland Hall for the Creative Arts

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

  Midnight Madness in Downtown Annapolis 2025

  Downtown Annapolis

  907+ Interested
• Wed, 03 Dec, 2025 - 06:00 PM

  An Evening of Holiday Radiance

  127 Lubrano Dr

  Free