| Date | Time | Event Name | Type | Genre | Venue | Address | Age | Price | |
|---|---|---|---|---|---|---|---|---|---|
 | ThuNov 20 | 8:00 PM | Vienna Teng | Music | Other | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | $20 |
FriNov 21 | 8:00 PM | Keb' Mo' | Music | Blues | Maryland Hall for the Creative Arts | 801 Chase Street | All Ages | Free | |
 | FriNov 21 | 8:00 PM | The Martin Sexton Abbey Road Show | Music | Blues | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | Free |
 | SatNov 22 | 8:00 PM | The Brit Pack: The Ultimate British Musi... | Music | Other | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | $20 |
 | SunNov 23 | 7:30 PM | Natalie Merchant | Music | Alternative | Maryland Hall for the Creative Arts | 801 Chase Street | All Ages | $50 |
 | SunNov 23 | 8:00 PM | Live Dead and Brothers: An All-Star Cele... | Music | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | $20 | |
 | TueNov 25 | 8:00 PM | Jim Messina | Music | Other | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | $50 |
 | FriNov 28 | 8:00 PM | U2TOPIA - The Mid Atlantic U2 Tribute Ba... | Music | Rock | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | Free |
 | SatNov 29 | 6:30 PM | Motown and More (6:30) | Music | Other | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | $20 |
| SunNov 30 | 7:00 PM | Hotel Paradise Orchestra (Dance Area) | Music | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | Free | |
 | TueDec 2 | 8:00 PM | Son Little with Candi Jenkins | Music | Other | Rams Head On Stage | 33 West St, Annapolis, MD | 18+ | $20 |
| WedDec 3 | 8:00 PM | The Empty Pockets | Music | Other | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | $20 |
 | ThuDec 4 | 6:30 PM | A Peter White Christmas with Mindi Abair... | Music | Pop | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | $50 |
| ThuDec 4 | 9:30 PM | A Peter White Christmas with Mindi Abair... | Music | Pop | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | $50 |
 | FriDec 5 | 8:00 PM | Pure Prairie League | Music | Country | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | $30 |
| SatDec 6 | 1:00 PM | Laura Tsaggaris (Matinee) | Music | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | Free | |
 | SatDec 6 | 8:00 PM | Atlanta Rhythm Section | Music | Other | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | $20 |
| SunDec 7 | 1:00 PM | Jeffrey Gaines and Sawyer Fredericks (Ma... | Music | Alternative | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | Free |
 | SunDec 7 | 7:00 PM | Tab Benoit w/ Jesse Dayton | Music | Blues | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | $20 |
 | SunDec 7 | 8:00 PM | Chris Isaak | Music | Alternative | Maryland Hall for the Creative Arts | 801 Chase Street | All Ages | $50 |
| MonDec 8 | 7:00 PM | Tab Benoit w/ Jesse Dayton | Music | Blues | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | $30 |
 | TueDec 9 | 8:00 PM | The Gilmour Project | Music | Other | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | Free |
WedDec 10 | 8:00 PM | The Milk Carton Kids w/ Humbird | Music | Country | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | Free | |
 | ThuDec 11 | 8:00 PM | Peter Mayer | Music | Rock | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | Free |
 | SatDec 13 | 8:30 PM | Carbon Leaf | Music | Alternative | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | $20 |
| SunDec 14 | 1:00 PM | Carbon Leaf | Music | Alternative | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | $20 |
 | SunDec 14 | 8:00 PM | Shakey Graves (Solo) with Clover County | Music | Country | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | $30 |
 | MonDec 15 | 7:00 PM | AMFMs An Annapolis Christmas | Fairs & Festivals | Fairs & Festivals | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | Free |
| TueDec 16 | 7:00 PM | AMFMs An Annapolis Christmas | Fairs & Festivals | Fairs & Festivals | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | Free |
| WedDec 17 | 8:00 PM | Jay Hurtt VI of Little Bird with Skribe | Music | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | Free | |
 | ThuDec 18 | 8:00 PM | Todd Barry (18 and Over) | Art & Theatre | Miscellaneous | Rams Head On Stage | 33 West St, Annapolis, MD | 18+ | $20 |
 | FriDec 19 | 6:30 PM | Paula Poundstone - 18+ | Art & Theatre | Rams Head On Stage | 33 West St, Annapolis, MD | 18+ | $20 | |
 | SatDec 20 | 12:00 PM | A SQRRL Holiday (Matinee) | Music | Other | Rams Head On Stage | 33 West St, Annapolis, MD | All Ages | Free |
 | SatDec 20 | 8:30 PM | Low Cut Connie with Kendra Morris | Music | Other | Rams Head On Stage | 33 West St, Annapolis, MD | 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 | Sports | Football | Navy Marine Corps Memorial Stadium | Rowe Blvd & Taylor Ave, 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 |
| 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 |