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 Kristi Allen

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 am - 1:45 pm Broadneck High School Jazz Band

11:30 am - 1:30 pm Songbird Collective

 2 pm - 5 pm Kristi Allen

 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

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

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

12 pm Santa Speedo Run on Main Street

​2 pm Classic Theatre of Maryland performs A Christmas Carol

2 pm - 3:30 pm Colonial Players perform A Christmas Carol

4:30 pm - 6 pm Colonial Players perform A Christmas Carol

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

7:30 pm - 9:30 pm Live Arts MD performs Handel's Messiah at St. Anne's Episcopal Church 

7 pm Ballet Theatre of Maryland performs The Nutcracker 

8 pm Classic Theatre of Maryland performs White Christmas

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Thursday Dec 18

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

7:30 pm Classic Theatre of Maryland performs A Christmas Carol

 

​Friday Dec 19

7 pm - 8:30 pm Watermark's Holiday Candlelight Stroll

7:30 pm Annapolis Symphony Orchestra's Holiday Pops concert at Maryland Hall

8 pm Classic Theatre of Maryland performs White Christmas

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Saturday Dec 20

7:30 am Naptown Half Marathon 

2 pm Classic Theatre of Maryland performs A Christmas Carol

7 pm Ballet Theatre of Maryland performs The Nutcracker 

7 pm - 8:30 pm Watermark's Holiday Candlelight Stroll

8 pm Classic Theatre of Maryland performs White Christmas

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Sunday Dec 21​

1pm Ballet Theatre of Maryland performs The Nutcracker 

2 pm Classic Theatre of Maryland performs White Christmas

4:30pm Ballet Theatre of Maryland performs The Nutcracker 

7:30 pm Classic Theatre of Maryland performs A Christmas Carol

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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.