This holiday market 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 2026

We are just starting to build out our entertainment schedule.

Please check back for alot more additions to this year's entertainment.

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Friday December 4​​​​

​5-515 pm Indian Creek School Dance 

 

Saturday December 5

​130-2 pm Connections Quartet 

2-3 pm Bates Middle School music 

3-330 pm Connections Quartet 

4-5 pm Outlet Dance Complex

5- 5:30 pm Talent Machine Company

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Sunday December 6

11 am - 1 pm Songbird Collective

6 - 630 pm The Cordelias Quartet 

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Friday December 11

​4- 4:30 pm St. Martin's Lutheran School

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Saturday December 12

11 am - 1:45 pm Naptown Sings

2 - 3 pm Bates Middle School Music

4 - 415 pm Edge Dance Complex

5 - 515 pm Edge Dance Complex

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Sunday December 13

11 am - 1 pm Songbird Collective Artists 

2- 2:40 pm Tuba Christmas

3 pm The Dance Center of Severna Park

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 Holiday Entertainment in the Annapolis area during the Annapolis Holiday Market 2026

Also attending these nearby events helps you create a full holiday weekend in Annapolis

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Friday December 4

5 pm - 10 pm Sandy Point State Park Lights on the Bay

730 pm Compass Rose Theater: It's a Wonderful Live Radio Play at Annapolis Mall

7:30 pm Colonial Players: The Best Christmas Pageant Ever

8 pm Classic Theatre of Maryland: A Christmas Carole

Saturday December 5

11 am Compass Rose Theater: It's a Wonderful Live Radio Play at Annapolis Mall

2 pm Classic Theatre of Maryland Holiday Inn

2 pm Colonial Players: The Best Christmas Pageant Ever

5 pm Colonial Players: The Best Christmas Pageant Ever

5 pm - 10 pm Sandy Point State Park Lights on the Bay

8 pm Classic Theatre of Maryland: A Christmas Carole

Sunday December 6

2 pm Classic Theatre of Maryland Holiday Inn

2 pm Colonial Players: The Best Christmas Pageant Ever

5 pm Colonial Players: The Best Christmas Pageant Ever

5 pm - 9 pm Sandy Point State Park Lights on the Bay

7:30 pm Classic Theatre of Maryland, Holiday Inn

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Friday December 11

5 pm -10 pm Sandy Point State Park Lights on the Bay

7:30 pm Colonial Players: The Best Christmas Pageant Ever

730pm Live Arts Maryland Celebration of Christmas at Maryland Hall

8 pm Classic Theatre of Maryland, Holiday Inn

Saturday December 12

1 pm Ballet Theatre of Maryland: The Nutcracker at Maryland Hall

2 pm Classic Theatre of Maryland: A Christmas Carole

2 pm Colonial Players: The Best Christmas Pageant Ever

5 pm Colonial Players: The Best Christmas Pageant Ever

5 pm - 10 pm Sandy Point State Park Lights on the Bay

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

730 pm Ballet Theatre of Maryland: The Nutcracker at Maryland Hall

8 pm Classic Theatre of Maryland: Holiday Inn

Sunday December 13

1 pm Ballet Theatre of Maryland: The Nutcracker at Maryland Hall

2 pm Classic Theatre of Maryland: Holiday Inn 

2 pm Colonial Players: The Best Christmas Pageant Ever

4:30 pm Ballet Theatre of Maryland: The Nutcracker at Maryland Hall

5 pm Colonial Players: The Best Christmas Pageant Ever

5 pm - 9 pm Sandy Point State Park: Lights on the Bay

7: 30 pm Classic Theatre of Maryland: A Christmas Carole​​​

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​​Be sure to leave enough time to stroll, tour, shop, dine, and spend the night while you visit Annapolis. Annapolis is often cited as one of the top Christmas Towns in the USA.

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