This year is the launch of the newest holiday market in the region that looks forward to becoming your holiday tradition. Check out all the entertainment and events below.

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Entertainment at the Annapolis Holiday Market

 

Thursday

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4 pm to 10 pm Live music from the Naval Academy Primary School Chorus and oyster ornament decorating with Chesapeake Family Media

 

Friday

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11am to 9pm DJ Jessie is spinning holiday tunes

 

4 pm to 8 pm Jolly Express Cruise departs hourly

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7pm Holiday Candlelight Stroll in historic Annapolis

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Saturday

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11 am to 6pm - Live music by Priddy Music Academy bands

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530pm - 830 pm - Fundraiser on the Harbor Queen for We Care and Friends

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

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Sunday

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4 pm to 7 pm Jolly Express Cruise​ departs hourly

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11 am to 5 pm - Live music by Priddy Music Academy bands

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Entertainment in downtown Annapolis near the Annapolis Holiday Market

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Thursday

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4 pm to midnight -It's the Midnight Madness Shopping event all through downtown Annapolis

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8 pm Peter Mayer: Stars & Promises Christmas Tour 

Rams Head On Stage

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Friday

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6 pm Celebration of Christmas Concert

Maryland Hall

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7 pm Holiday Candlelight Stroll

Watermark Tours Charters Cruises

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830 pm Carbon Leaf Concert

Rams Head On Stage

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Saturday

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3pm Tuba Christmas outdoor concert on Church Circle

St Annes Church

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3 pm & 830 pm Carbon Leaf Concert

Rams Head On Stage

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415 pm  Lights Parade Holiday Package

Watermark Tours Charters Cruises

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Sunday

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1pm Carbon Leaf Concert

Rams Head On Stage

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730pm  Pam Tillis: “Belles & Bows” Country Hits & Christmas Favorites

Rams Head On Stage

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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.