The newest holiday market in the region is gaining regional attention and accolades in the press, and we look forward to becoming part of your annual holiday traditions. Check out all the entertainment and events below. Let us know if you are a community group interested in performing this year or next year.

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Entertainment Schedule at the Annapolis Holiday Market 2025

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Saturday Dec 13

11 am - 9 pm Holiday DJ

4 pm - 5 pm Apex Arts Bate Middle School Choir

5 pm Meet Santa Claus - Bring your camera for free pictures 

5:30 pm - 8:30 pm Michael K 

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Thursday Dec 18

4 pm - 9 pm Holiday DJ​

6 pm - 9 pm TBA

6 pm - 9 pm Sons of the Severn caroling through​

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Friday Dec 19

11 am - 9 pm Holiday DJ

 2 pm - 5 pm The Magnificent Brass band

 5:30 pm - 7:30 pm Naptown Sings and Plays! 

 7:30 pm - 9 pm SOL, Severna Park High School Acapella Ensemble​

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Saturday Dec 20

11 am - 9 pm Holiday DJ

11:30 am - 1:30 pm Songbird Collective

 2 pm - 5 pm TBA

 2 pm - 3:30 pm SOL, Severna Park High School Acapella Ensemble

 5 pm - 8 pm The Magnificent Brass band

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Sunday Dec 21

 11am - 2 pm Priddy Music Academy Bands ​

 2 pm - 3:30 pm SOL, Severna Park High School Acapella Ensemble

 2 pm - 5 pm The Magnificent Brass band

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Entertainment in the downtown Annapolis area during the Annapolis Holiday Market

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Saturday Dec 13

9 am - 12 pm Governor's Open House

10am - 5pm Christmas Tree Exhibit inside the State House

12 pm Santa Speedo Run on Main Street

10 am - 4 pm Kwanza Celebration at the Banneker-Douglass-Tubman Museum

 6 pm - 8 pm - Eastport Yacht Club's Light Parade

Live Arts MD will perform Handel's Messiah at St. Anne's Episcopal Church 

Ballet Theatre of Maryland will perform The Nutcracker 

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Thursday Dec 18

4 pm to Midnight - Midnight Madness sales event at stores throughout downtown Annapolis

 

​Friday Dec 19

Annapolis Symphony Orchestra's Holiday Pops concert at Maryland Hall

Ballet Theatre of Maryland will perform The Nutcracker 

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Saturday Dec 20

7:30 am Naptown Half Marathon 

Ballet Theatre of Maryland will perform The Nutcracker 

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Saturday Dec 21​

Ballet Theatre of Maryland will perform The Nutcracker 

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​​Be sure to plan to leave enough time to stroll, tour, shop, and dine throughout the beautifully decorated streets of downtown Annapolis. Annapolis is frequently mentioned as one of the top Christmas Towns in the USA to visit.

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Admission is free to the Annapolis Holiday Market and tour buses are welcome.