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 2026

This year's entertainment schedule is coming soon

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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

730 pm Colonial Players of Annapolis: It's a Wonderful Live Radio Play at Annapolis Mall

8 pm Classic Theatre of Maryland: A Christmas Carole

Saturday December 5

11 am Colonial Players of Annapolis: It's a Wonderful Live Radio Play at Annapolis Mall

2 pm Classic Theatre of Maryland Holiday Inn

8 pm Classic Theatre of Maryland: A Christmas Carole

Sunday December 6

2 pm Classic Theatre of Maryland Holiday Inn

7:30 pm Classic Theatre of Maryland, Holiday Inn

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Friday December 11

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

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 

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

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 frequently mentioned as one of the top Christmas Towns in the USA to visit.

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