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. If you are a community group interested in making an appearance this year or next year let us know.

​

Entertainment Schedule at the Annapolis Holiday Market 2023

​

Thursday

 4 pm - 7 pm Jolly Express Cruise​ departs hourly

 4 pm - 6 pm Spice Band

 6 pm - 9 pm DJ Jesse

 6 pm - 9 pm Navel Academy Primary singers and Design in Motion Dancers

 6 pm - 9 pm Music by Ryan Kozel 

 4 pm - 10 pm Meet Santa Claus - Bring your camera for free pictures

​

Friday

11 am - 9 pm Face Painting and Balloon Animals

11 am - 4 pm Meet Santa Claus - Bring your camera for free pictures

11 am - 9 pm DJ Jesse

 3 pm - 8 pm Jolly Express Cruise departs hourly

 6 pm - 8 pm Naptown Sings 

​

Saturday

11 am - 1 pm Unified Jazz Ensemble

 1 pm - 3 pm JazzMaTazz Band

 2 pm - 9 pm Meet Santa Claus - Bring your camera for free pictures

 3:30 pm - 6 pm Hardway Connection Band

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

 5:30 pm Queen of all Fund Drives aboard the Harbor Queen

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

​

Sunday

11 am - 2 pm Priddy Music Acadamy Bands

 2 pm - 3 pm Voices in Praise Choir

 3:15 pm - 5 pm Honey Sol Band

 3 pm - 7 pm Jolly Express Cruise​ departs hourly

​

​

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

7:30 pm Christmas Carol - Classic Theatre of Maryland

​

Friday

1 pm and 8 pm White Christmas - Classic Theatre of Maryland

7 pm Holiday Candlelight Stroll 

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

​

Saturday

2 pm Christmas Carol - Classic Theatre of Maryland

3 pm Annapolis Tuba Christmas - St. Anne's Church 

11 am Kwanzaa Celebration - Banneker Douglas Museum

8 pm White Christmas - Classic Theatre of Maryland

​

Sunday 

2 pm White Christmas - Classic Theatre of Maryland

7:30 pm Christmas Carol - Classic Theatre of Maryland

​

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.

​

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