Entertainment events in Annapolis in December

• Fri, 26 Dec, 2025 - 05:00 PM

  Siren's Call

  The Westin Annapolis

  Free
• Fri, 26 Dec, 2025 - 08:00 PM

  Jimmie's Chicken Shack Holidaze Show

  Rams Head On Stage

  192+ Interested
• Sun, 28 Dec, 2025 - 08:00 PM

  Pressing Strings

  Rams Head On Stage

  76+ Interested
• Fri, 26 Dec, 2025 - 08:00 PM

  2nd Generation @ Dark Horse!

  985 Bay Ridge Rd, Annapolis, MD 21403-3934, United States

  25+ Interested
• Wed, 24 Dec, 2025 - 06:30 PM

  🎷 Jazz Night at Reynolds Tavern — Every Wednesday! 🎷

  7 Church Cir, Annapolis, MD, United States, Maryland 21401
• Mon, 29 Dec Onwards

  The Seldom Scene

  Rams Head On Stage
• Sat, 27 Dec, 2025 - 04:00 PM

  Military Bowl: Pittsburgh vs East Carolina

  Navy-Marine Corps Memorial Stadium
• Fri, 26 Dec, 2025 - 07:00 PM

  Military Bowl

  Navy-Marine Corps Memorial Stadium
• Tue, 30 Dec, 2025 - 01:00 AM

  Parking Stephen Kellogg

  Rams Head On Stage - Annapolis
• Sat, 27 Dec, 2025 - 04:00 PM

  Parking Military Bowl: Pittsburgh vs East Carolina

  Navy-Marine Corps Memorial Stadium
• Sat, 27 Dec, 2025 - 09:00 PM

  12/27 - ilyAIMY @ Dark Horse Annapolis (full band!)

  Dark Horse Annapolis

  26+ Interested
• Sat, 27 Dec, 2025 - 07:00 PM

  Sinners at 49 West

  49 West Coffeehouse, Winebar & Gallery

  6+ Interested
• Fri, 26 Dec, 2025 - 09:00 PM

  Blackwall Hitch Annapolis

  Blackwall Hitch Annapolis