Entertainment events in Annapolis

• Fri, 19 Dec, 2025 - 07:30 PM

  Holiday Pops at Maryland Hall

  Maryland Hall for the Creative Arts

  16+ Interested
• Sun, 21 Dec, 2025 - 07:30 PM

  Jon McLaughlin & Friends: Home For The Holidays

  Rams Head On Stage

  28+ Interested
• Fri, 28 Nov, 2025 - 05:00 PM

  Siren's Call

  The Westin Annapolis

  Free
• Sat, 06 Dec, 2025 - 01:00 PM

  Laura Tsaggaris (Matinee)

  Rams Head On Stage

  4+ Interested
• Sat, 06 Dec, 2025 - 07:00 PM

  Chris Isaak

  Maryland Hall For The Creative Arts
• Sat, 13 Dec, 2025 - 03:30 PM

  Carbon Leaf: Carbon Leaf: 'I Want To Be Leaf' Tour 2025

  Rams Head On Stage

  48+ Interested
• Tue, 02 Dec, 2025 - 05:00 PM

  Tides & Tunes

  The Westin Annapolis

  Free
• Sat, 13 Dec, 2025 - 07:00 PM

  Shakey Graves

  Rams Head On Stage
• Fri, 26 Dec, 2025 - 08:00 PM

  Jimmie's Chicken Shack Holidaze Show

  Rams Head On Stage

  184+ Interested
• Sat, 13 Dec, 2025 - 08:30 PM

  Carbon Leaf: 'I Want To Be Leaf' Tour 2025

  Rams Head On Stage

  30+ Interested
• Fri, 05 Dec, 2025 - 07:30 PM

  Live Arts Maryland presents Bluegrass Nutcracker

  Annapolis Mall

  USD 34
• Sat, 06 Dec, 2025 - 06:00 PM

  2025 FRA 24 Holiday Party

  Fleet Reserve Club Of Annapolis

  USD 66
• Thu, 11 Dec, 2025 - 08:00 PM

  Peter Mayer: A Stars and Promises Christmas 2025

  Rams Head On Stage

  104+ Interested
• Thu, 22 Jan, 2026 - 08:00 PM

  Cash Unchained – The Ultimate Johnny Cash Tribute

  Rams Head On Stage

  54+ Interested
• Sat, 19 Sep, 2026 - 10:00 AM

  BAYGRASS 2026: Annapolis Baygrass Music Festival 9/19-20

  1100 E College Pkwy, Annapolis, MD, United States, Maryland 21409

  502+ Interested