The newest holiday market in the region is gaining regional attention and accolades in the press and looks 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 making an appearance this year or next year.

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Entertainment Schedule at the Annapolis Holiday Market 2024

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Thursday

 4 pm - 7 pm Jolly Express Cruise​ departs hourly

Meet Santa Claus - Bring your camera for free pictures

More entertainment to be announced soon !

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Friday

Meet Santa Claus - Bring your camera for free pictures

 3 pm - 8 pm Jolly Express Cruise departs hourly

More entertainment to be announced soon !

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Saturday

Meet Santa Claus - Bring your camera for free pictures

 5 pm Lights Parade Dinner Cruise with Ken's Creative Kitchen

 6 pm - 8 pm - It's the Eastport Yacht Club Lights Parade

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Sunday

1 pm Tuba Christmas Concert

3 pm - 7 pm Jolly Express Cruise​ departs hourly

More entertainment to be announced soon !

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Entertainment in the downtown Annapolis area during the Annapolis Holiday Market

 

Thursday

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

 

​Friday

 8 pm White Christmas - Classic Theatre of Maryland

7 pm Holiday Candlelight Stroll 

8 pm Celebration of Christmas - Maryland Hall for the Creative Arts

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Saturday

11 am Annapolis Speedo Run - Main Street / Obriens

11 am Kwanzaa Celebration - Banneker Douglas Museum

7 pm Nutcracker - Ballet Theater of Maryland/MD Hall

8 pm White Christmas - Classic Theatre of Maryland

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Sunday 

1 pm Nutcracker - Ballet Theater of Maryland/MD Hall

2 pm White Christmas - Classic Theatre of Maryland

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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.