| Event | Venue | Date/Time |
| Tyrus - Comedian | DoubleTree by Hilton Hotel Annapolis Annapolis, MD | Sunday 01/24/2027 19:30:00 view tickets |
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| The Ultimate Acoustic Rock Show | Rams Head On Stage Annapolis, MD | Sunday 02/07/2027 13:00:00 view tickets |
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| The Secret Garden | Main Stage At Classic Theatre of Maryland Annapolis, MD | Thursday 07/08/2027 19:30:00 view tickets |
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| The Secret Garden | Main Stage At Classic Theatre of Maryland Annapolis, MD | Friday 07/09/2027 20:00:00 view tickets |
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| The Secret Garden | Main Stage At Classic Theatre of Maryland Annapolis, MD | Saturday 07/10/2027 14:00:00 view tickets |
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| The Secret Garden | Main Stage At Classic Theatre of Maryland Annapolis, MD | Saturday 07/10/2027 20:00:00 view tickets |
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| The Secret Garden | Main Stage At Classic Theatre of Maryland Annapolis, MD | Sunday 07/11/2027 14:00:00 view tickets |
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| The Secret Garden | Main Stage At Classic Theatre of Maryland Annapolis, MD | Thursday 07/15/2027 19:30:00 view tickets |
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| The Secret Garden | Main Stage At Classic Theatre of Maryland Annapolis, MD | Friday 07/16/2027 20:00:00 view tickets |
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| The Secret Garden | Main Stage At Classic Theatre of Maryland Annapolis, MD | Saturday 07/17/2027 14:00:00 view tickets |
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| The Secret Garden | Main Stage At Classic Theatre of Maryland Annapolis, MD | Saturday 07/17/2027 20:00:00 view tickets |
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| The Secret Garden | Main Stage At Classic Theatre of Maryland Annapolis, MD | Sunday 07/18/2027 14:00:00 view tickets |
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| The Secret Garden | Main Stage At Classic Theatre of Maryland Annapolis, MD | Thursday 07/22/2027 19:30:00 view tickets |
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| The Secret Garden | Main Stage At Classic Theatre of Maryland Annapolis, MD | Friday 07/23/2027 20:00:00 view tickets |
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| The Secret Garden | Main Stage At Classic Theatre of Maryland Annapolis, MD | Saturday 07/24/2027 14:00:00 view tickets |
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| The Secret Garden | Main Stage At Classic Theatre of Maryland Annapolis, MD | Saturday 07/24/2027 20:00:00 view tickets |
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| The Secret Garden | Main Stage At Classic Theatre of Maryland Annapolis, MD | Sunday 07/25/2027 14:00:00 view tickets |
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| Steven Page | Rams Head On Stage Annapolis, MD | Monday 12/21/2026 20:00:00 view tickets |
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| Sons of Cream: Kofi Baker, Malcolm Bruce & Rob Johnson | Rams Head On Stage Annapolis, MD | Sunday 04/25/2027 20:00:00 view tickets |
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| She Stoops To Conquer | Main Stage At Classic Theatre of Maryland Annapolis, MD | Thursday 03/04/2027 19:30:00 view tickets |
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| She Stoops To Conquer | Main Stage At Classic Theatre of Maryland Annapolis, MD | Friday 03/05/2027 20:00:00 view tickets |
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| She Stoops To Conquer | Main Stage At Classic Theatre of Maryland Annapolis, MD | Saturday 03/06/2027 14:00:00 view tickets |
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| She Stoops To Conquer | Main Stage At Classic Theatre of Maryland Annapolis, MD | Saturday 03/06/2027 20:00:00 view tickets |
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| She Stoops To Conquer | Main Stage At Classic Theatre of Maryland Annapolis, MD | Sunday 03/07/2027 14:00:00 view tickets |
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| She Stoops To Conquer | Main Stage At Classic Theatre of Maryland Annapolis, MD | Thursday 03/11/2027 19:30:00 view tickets |
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| She Stoops To Conquer | Main Stage At Classic Theatre of Maryland Annapolis, MD | Friday 03/12/2027 20:00:00 view tickets |
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| She Stoops To Conquer | Main Stage At Classic Theatre of Maryland Annapolis, MD | Saturday 03/13/2027 14:00:00 view tickets |
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| She Stoops To Conquer | Main Stage At Classic Theatre of Maryland Annapolis, MD | Saturday 03/13/2027 20:00:00 view tickets |
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| She Stoops To Conquer | Main Stage At Classic Theatre of Maryland Annapolis, MD | Sunday 03/14/2027 14:00:00 view tickets |
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| She Stoops To Conquer | Main Stage At Classic Theatre of Maryland Annapolis, MD | Thursday 03/18/2027 19:30:00 view tickets |
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| She Stoops To Conquer | Main Stage At Classic Theatre of Maryland Annapolis, MD | Friday 03/19/2027 20:00:00 view tickets |
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| She Stoops To Conquer | Main Stage At Classic Theatre of Maryland Annapolis, MD | Saturday 03/20/2027 14:00:00 view tickets |
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| She Stoops To Conquer | Main Stage At Classic Theatre of Maryland Annapolis, MD | Saturday 03/20/2027 20:00:00 view tickets |
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| She Stoops To Conquer | Main Stage At Classic Theatre of Maryland Annapolis, MD | Sunday 03/21/2027 14:00:00 view tickets |
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| S. Carey | Rams Head On Stage Annapolis, MD | Tuesday 12/08/2026 20:00:00 view tickets |
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| Piff the Magic Dragon | Maryland Hall For The Creative Arts Annapolis, MD | Wednesday 02/03/2027 19:30:00 view tickets |
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| Paul Mecurio | Rams Head On Stage Annapolis, MD | Saturday 11/14/2026 20:00:00 view tickets |
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| PARKING: Navy Midshipmen vs. Memphis Tigers | Navy Marine Corps Memorial Stadium Parking Lots Annapolis, MD | Saturday 11/21/2026 TBA view tickets |
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| Navy Midshipmen vs. Penn State Berks Nittany Lions | Alumni Hall - MD Annapolis, MD | Tuesday 11/24/2026 16:30:00 view tickets |
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| Navy Midshipmen vs. Memphis Tigers | Navy Marine Corps Memorial Stadium Annapolis, MD | Saturday 11/21/2026 12:00:00 view tickets |
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| Navy Midshipmen vs. Hampton Pirates | Alumni Hall - MD Annapolis, MD | Saturday 11/14/2026 16:00:00 view tickets |
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| Military Bowl | Navy Marine Corps Memorial Stadium Annapolis, MD | Monday 12/28/2026 14:00:00 view tickets |
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| Mickey Guyton | Rams Head On Stage Annapolis, MD | Wednesday 12/09/2026 20:00:00 view tickets |
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| Matthew Morrison | Rams Head On Stage Annapolis, MD | Wednesday 03/17/2027 20:00:00 view tickets |
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| Marc Roberge | Rams Head On Stage Annapolis, MD | Wednesday 12/16/2026 20:00:00 view tickets |
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| Lalah Hathaway | Maryland Hall For The Creative Arts Annapolis, MD | Monday 11/16/2026 20:00:00 view tickets |
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| KT Tunstall | Rams Head On Stage Annapolis, MD | Thursday 04/22/2027 20:00:00 view tickets |
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| July Cabaret | Cabaret Room at Classic Theatre of Maryland Annapolis, MD | Monday 07/12/2027 19:30:00 view tickets |
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| July Cabaret | Cabaret Room at Classic Theatre of Maryland Annapolis, MD | Tuesday 07/13/2027 19:30:00 view tickets |
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| Jon McLaughlin | Rams Head On Stage Annapolis, MD | Friday 12/04/2026 20:00:00 view tickets |
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| John Splithoff | Rams Head On Stage Annapolis, MD | Saturday 11/21/2026 14:00:00 view tickets |
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| Jessica Michelle Singleton | Rams Head On Stage Annapolis, MD | Saturday 01/23/2027 20:00:00 view tickets |
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| Jessica Kirson | Maryland Hall For The Creative Arts Annapolis, MD | Thursday 01/28/2027 20:00:00 view tickets |
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| Irving Berlin's Holiday Inn | Main Stage At Classic Theatre of Maryland Annapolis, MD | Friday 11/27/2026 20:00:00 view tickets |
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| Irving Berlin's Holiday Inn | Main Stage At Classic Theatre of Maryland Annapolis, MD | Saturday 11/28/2026 14:00:00 view tickets |
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| Irving Berlin's Holiday Inn | Main Stage At Classic Theatre of Maryland Annapolis, MD | Saturday 11/28/2026 20:00:00 view tickets |
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| Irving Berlin's Holiday Inn | Main Stage At Classic Theatre of Maryland Annapolis, MD | Sunday 11/29/2026 14:00:00 view tickets |
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| Irving Berlin's Holiday Inn | Main Stage At Classic Theatre of Maryland Annapolis, MD | Saturday 12/05/2026 14:00:00 view tickets |
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| Irving Berlin's Holiday Inn | Main Stage At Classic Theatre of Maryland Annapolis, MD | Sunday 12/06/2026 14:00:00 view tickets |
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| Irving Berlin's Holiday Inn | Main Stage At Classic Theatre of Maryland Annapolis, MD | Sunday 12/06/2026 19:30:00 view tickets |
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| Irving Berlin's Holiday Inn | Main Stage At Classic Theatre of Maryland Annapolis, MD | Wednesday 12/09/2026 19:30:00 view tickets |
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| Irving Berlin's Holiday Inn | Main Stage At Classic Theatre of Maryland Annapolis, MD | Friday 12/11/2026 20:00:00 view tickets |
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| Irving Berlin's Holiday Inn | Main Stage At Classic Theatre of Maryland Annapolis, MD | Saturday 12/12/2026 20:00:00 view tickets |
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| Irving Berlin's Holiday Inn | Main Stage At Classic Theatre of Maryland Annapolis, MD | Sunday 12/13/2026 14:00:00 view tickets |
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| Irving Berlin's Holiday Inn | Main Stage At Classic Theatre of Maryland Annapolis, MD | Wednesday 12/16/2026 19:30:00 view tickets |
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| Irving Berlin's Holiday Inn | Main Stage At Classic Theatre of Maryland Annapolis, MD | Saturday 12/19/2026 20:00:00 view tickets |
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| Irving Berlin's Holiday Inn | Main Stage At Classic Theatre of Maryland Annapolis, MD | Sunday 12/20/2026 14:00:00 view tickets |
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| Irving Berlin's Holiday Inn | Main Stage At Classic Theatre of Maryland Annapolis, MD | Tuesday 12/22/2026 19:30:00 view tickets |
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| Irving Berlin's Holiday Inn | Main Stage At Classic Theatre of Maryland Annapolis, MD | Wednesday 12/23/2026 14:00:00 view tickets |
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| Irving Berlin's Holiday Inn | Main Stage At Classic Theatre of Maryland Annapolis, MD | Thursday 12/24/2026 18:00:00 view tickets |
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| Irving Berlin's Holiday Inn | Main Stage At Classic Theatre of Maryland Annapolis, MD | Saturday 12/26/2026 14:00:00 view tickets |
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| Irving Berlin's Holiday Inn | Main Stage At Classic Theatre of Maryland Annapolis, MD | Sunday 12/27/2026 19:30:00 view tickets |
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| Herman's Hermits & Peter Noone | Rams Head On Stage Annapolis, MD | Sunday 11/22/2026 16:30:00 view tickets |
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| Herman's Hermits & Peter Noone | Rams Head On Stage Annapolis, MD | Sunday 11/22/2026 19:30:00 view tickets |
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| Gary Gulman: 7th Hour | Rams Head On Stage Annapolis, MD | Saturday 01/30/2027 19:30:00 view tickets |
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| G. Love & Special Sauce | Rams Head On Stage Annapolis, MD | Tuesday 01/26/2027 20:00:00 view tickets |
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| G. Love & Special Sauce | Rams Head On Stage Annapolis, MD | Wednesday 01/27/2027 20:00:00 view tickets |
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| Fallin' Free - Tribute to Tom Petty and The Heartbreakers | Rams Head On Stage Annapolis, MD | Friday 01/22/2027 20:00:00 view tickets |
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| David Phelps | Kannapolis Church of God Kannapolis, NC | Sunday 03/21/2027 19:00:00 view tickets |
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| Dave Attell | Rams Head On Stage Annapolis, MD | Saturday 03/13/2027 18:30:00 view tickets |
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| Dave Attell | Rams Head On Stage Annapolis, MD | Saturday 03/13/2027 21:30:00 view tickets |
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| Dames At Sea | Main Stage At Classic Theatre of Maryland Annapolis, MD | Thursday 04/29/2027 19:30:00 view tickets |
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| Dames At Sea | Main Stage At Classic Theatre of Maryland Annapolis, MD | Friday 04/30/2027 20:00:00 view tickets |
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| Dames At Sea | Main Stage At Classic Theatre of Maryland Annapolis, MD | Saturday 05/01/2027 14:00:00 view tickets |
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| Dames At Sea | Main Stage At Classic Theatre of Maryland Annapolis, MD | Saturday 05/01/2027 20:00:00 view tickets |
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| Dames At Sea | Main Stage At Classic Theatre of Maryland Annapolis, MD | Sunday 05/02/2027 14:00:00 view tickets |
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| Dames At Sea | Main Stage At Classic Theatre of Maryland Annapolis, MD | Thursday 05/06/2027 19:30:00 view tickets |
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| Dames At Sea | Main Stage At Classic Theatre of Maryland Annapolis, MD | Friday 05/07/2027 20:00:00 view tickets |
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| Dames At Sea | Main Stage At Classic Theatre of Maryland Annapolis, MD | Saturday 05/08/2027 14:00:00 view tickets |
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| Dames At Sea | Main Stage At Classic Theatre of Maryland Annapolis, MD | Saturday 05/08/2027 20:00:00 view tickets |
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| Dames At Sea | Main Stage At Classic Theatre of Maryland Annapolis, MD | Sunday 05/09/2027 14:00:00 view tickets |
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| Dames At Sea | Main Stage At Classic Theatre of Maryland Annapolis, MD | Thursday 05/13/2027 19:30:00 view tickets |
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| Dames At Sea | Main Stage At Classic Theatre of Maryland Annapolis, MD | Friday 05/14/2027 20:00:00 view tickets |
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| Dames At Sea | Main Stage At Classic Theatre of Maryland Annapolis, MD | Saturday 05/15/2027 14:00:00 view tickets |
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| Dames At Sea | Main Stage At Classic Theatre of Maryland Annapolis, MD | Saturday 05/15/2027 20:00:00 view tickets |
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| Dames At Sea | Main Stage At Classic Theatre of Maryland Annapolis, MD | Sunday 05/16/2027 14:00:00 view tickets |
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| Cris Jacobs | Rams Head On Stage Annapolis, MD | Saturday 01/16/2027 20:00:00 view tickets |
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| Carbon Leaf | Rams Head On Stage Annapolis, MD | Saturday 12/12/2026 15:30:00 view tickets |
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| Candlelight: Tribute to Coldplay & Imagine Dragons | Maryland Hall For The Creative Arts Annapolis, MD | Saturday 11/21/2026 18:45:00 view tickets |
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| Ballet Theatre of Maryland: The Nutcracker | Maryland Hall For The Creative Arts Annapolis, MD | Saturday 12/12/2026 13:00:00 view tickets |
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| Ballet Theatre of Maryland: The Nutcracker | Maryland Hall For The Creative Arts Annapolis, MD | Saturday 12/12/2026 19:00:00 view tickets |
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| Ballet Theatre of Maryland: The Nutcracker | Maryland Hall For The Creative Arts Annapolis, MD | Sunday 12/13/2026 13:00:00 view tickets |
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| Ballet Theatre of Maryland: The Nutcracker | Maryland Hall For The Creative Arts Annapolis, MD | Sunday 12/13/2026 16:30:00 view tickets |
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| Ballet Theatre of Maryland: The Nutcracker | Maryland Hall For The Creative Arts Annapolis, MD | Saturday 12/19/2026 13:00:00 view tickets |
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| Ballet Theatre of Maryland: The Nutcracker | Maryland Hall For The Creative Arts Annapolis, MD | Saturday 12/19/2026 19:00:00 view tickets |
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| Ballet Theatre of Maryland: The Nutcracker | Maryland Hall For The Creative Arts Annapolis, MD | Sunday 12/20/2026 13:00:00 view tickets |
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| Ballet Theatre of Maryland: The Nutcracker | Maryland Hall For The Creative Arts Annapolis, MD | Sunday 12/20/2026 16:30:00 view tickets |
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| August Cabaret | Cabaret Room at Classic Theatre of Maryland Annapolis, MD | Monday 08/16/2027 19:30:00 view tickets |
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| August Cabaret | Cabaret Room at Classic Theatre of Maryland Annapolis, MD | Tuesday 08/17/2027 19:30:00 view tickets |
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| Annapolis Spring Sailboat Show | Annapolis City Dock Annapolis, MD | Friday 04/23/2027 10:00:00 view tickets |
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| Annapolis Spring Sailboat Show | Annapolis City Dock Annapolis, MD | Saturday 04/24/2027 10:00:00 view tickets |
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| Annapolis Spring Sailboat Show | Annapolis City Dock Annapolis, MD | Sunday 04/25/2027 10:00:00 view tickets |
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| A SQRRL! Holiday Matinee | Rams Head On Stage Annapolis, MD | Saturday 12/19/2026 12:00:00 view tickets |
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| A Christmas Carol | Main Stage At Classic Theatre of Maryland Annapolis, MD | Thursday 12/03/2026 19:30:00 view tickets |
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| A Christmas Carol | Main Stage At Classic Theatre of Maryland Annapolis, MD | Friday 12/04/2026 20:00:00 view tickets |
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| A Christmas Carol | Main Stage At Classic Theatre of Maryland Annapolis, MD | Saturday 12/05/2026 20:00:00 view tickets |
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| A Christmas Carol | Main Stage At Classic Theatre of Maryland Annapolis, MD | Thursday 12/10/2026 19:30:00 view tickets |
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| A Christmas Carol | Main Stage At Classic Theatre of Maryland Annapolis, MD | Saturday 12/12/2026 14:00:00 view tickets |
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| A Christmas Carol | Main Stage At Classic Theatre of Maryland Annapolis, MD | Sunday 12/13/2026 19:30:00 view tickets |
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| A Christmas Carol | Main Stage At Classic Theatre of Maryland Annapolis, MD | Thursday 12/17/2026 19:30:00 view tickets |
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| A Christmas Carol | Main Stage At Classic Theatre of Maryland Annapolis, MD | Saturday 12/19/2026 14:00:00 view tickets |
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| A Christmas Carol | Main Stage At Classic Theatre of Maryland Annapolis, MD | Sunday 12/20/2026 19:30:00 view tickets |
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| A Christmas Carol | Main Stage At Classic Theatre of Maryland Annapolis, MD | Monday 12/21/2026 19:30:00 view tickets |
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| A Christmas Carol | Main Stage At Classic Theatre of Maryland Annapolis, MD | Wednesday 12/23/2026 19:30:00 view tickets |
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| A Christmas Carol | Main Stage At Classic Theatre of Maryland Annapolis, MD | Thursday 12/24/2026 14:00:00 view tickets |
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| A Christmas Carol | Main Stage At Classic Theatre of Maryland Annapolis, MD | Saturday 12/26/2026 20:00:00 view tickets |
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| A Christmas Carol | Main Stage At Classic Theatre of Maryland Annapolis, MD | Sunday 12/27/2026 14:00:00 view tickets |
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