| Date | Time | Event Name | Type | Genre | Venue | Address | Age | Price | |
|---|---|---|---|---|---|---|---|---|---|
 | SunDec 21 | 12:00 PM | Navy Midshipmen Mens Basketball vs. Rose... | Sports | Basketball | Alumni Hall - MD | United States Naval Academy | All Ages | Free |
 | SunDec 21 | 12:30 PM | Happy Holidays Drag Brunch (16 and Over) | Art & Theatre | Miscellaneous | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | Free |
 | SunDec 21 | 7:30 PM | Jon McLaughlin | Music | Blues | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | Free |
 | TueDec 23 | 8:00 PM | The Dirty Grass Players with The Black-E... | Music | Other | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | Free |
 | FriDec 26 | 8:00 PM | Jimmie's Chicken Shack Holidaze Show | Music | Other | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | Free |
 | SatDec 27 | 11:00 AM | Military Bowl: Pitt vs East Carolina | Sports | Football | Navy Marine Corps Memorial Stadium | Rowe Blvd & Taylor Ave, Annapolis, MD | All Ages | Free |
 | SatDec 27 | 8:00 PM | Pressing Strings | Music | Other | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | Free |
 | SunDec 28 | 8:00 PM | Pressing Strings | Music | Other | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | Free |
 | MonDec 29 | 8:00 PM | Stephen Kellogg's Old Friends Tour feat.... | Music | Pop | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | Free |
 | TueDec 30 | 8:00 PM | The Seldom Scene | Music | Other | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | Free |
| WedDec 31 | 1:00 PM | Navy Midshipmen Mens Basketball vs. Bost... | Sports | Basketball | Alumni Hall - MD | United States Naval Academy | All Ages | Free |
| FriJan 2 | 8:00 PM | Last Train Home | Music | Other | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | Free |
 | SatJan 3 | 8:00 PM | Fan Halen: The World???s Most Authentic ... | Music | Other | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | Free |
| WedJan 7 | 7:00 PM | Navy Midshipmen Mens Basketball vs. Buck... | Sports | Basketball | Alumni Hall - MD | United States Naval Academy | All Ages | Free |
 | FriJan 9 | 8:00 PM | Alison Brown Quintet | Music | Other | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | Free |
| SatJan 10 | 2:00 PM | Navy Midshipmen Mens Basketball vs. Lafa... | Sports | Basketball | Alumni Hall - MD | United States Naval Academy | All Ages | Free |
 | SunJan 11 | 1:00 PM | Ana Popovic (Matinee) | Music | Blues | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | Free |
| SunJan 11 | 8:00 PM | Dead Letter Office - REM Tribute | Music | Other | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | Free |
 | WedJan 14 | 8:00 PM | Don Jovi: The Ultimate Tribute to the Mu... | Music | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | Free | |
 | ThuJan 15 | 8:00 PM | Good Stuff: The Music of Sting, Stevie W... | Music | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | Free | |
| FriJan 16 | 8:00 PM | Danah Denice | Music | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | Free | |
 | SatJan 17 | 8:00 PM | Jarrod Lawson | Music | Other | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | Free |
SunJan 18 | 8:00 PM | Avery Sunshine | Music | Other | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | Free | |
| WedJan 21 | 7:00 PM | Navy Midshipmen Mens Basketball vs. Holy... | Sports | Basketball | Alumni Hall - MD | United States Naval Academy | All Ages | Free |
 | ThuJan 22 | 8:00 PM | Cash Unchained | Music | Other | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | Free |
 | FriJan 23 | 8:00 PM | Bruce In The USA-Tribute | Music | Rock | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | Free |
| SatJan 24 | 1:30 PM | Navy Midshipmen Mens Basketball vs. Army... | Sports | Basketball | Alumni Hall - MD | United States Naval Academy | All Ages | Free |
| SatJan 24 | 8:00 PM | Bruce In The USA-Tribute | Music | Rock | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | Free |
 | SunJan 25 | 8:00 PM | Dave Matthews Tribute Band | Music | Other | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | Free |
| FriJan 30 | 8:00 PM | Sweet Leda and Lower Case Blues (Dance A... | Music | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | Free | |
| SatJan 31 | 4:00 PM | Navy Midshipmen Mens Basketball vs. Loyo... | Sports | Basketball | Alumni Hall - MD | United States Naval Academy | All Ages | Free |
 | SatJan 31 | 8:30 PM | The Chuck Brown Band (Dance Area) | Music | Blues | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | Free |
 | SunFeb 1 | 1:00 PM | Billy Price Band and The Chris O'Leary B... | Music | Other | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | Free |
 | SunFeb 1 | 8:00 PM | Satisfaction - International Rolling Sto... | Music | Undefined | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | Free |
 | TueFeb 3 | 8:00 PM | G Love & Special Sauce w/ Makua | Music | Alternative | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | Free |
| WedFeb 4 | 8:00 PM | G Love & Special Sauce | Music | Alternative | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | Free |
| ThuFeb 5 | 8:00 PM | Mike Dawes | Music | Other | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | Free |
 | FriFeb 6 | 8:00 PM | Dar Williams with Seth Glier | Music | Country | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | Free |
| SatFeb 7 | 4:00 PM | Navy Midshipmen Mens Basketball vs. Amer... | Sports | Basketball | Alumni Hall - MD | United States Naval Academy | All Ages | Free |