entertainment at
the Annapolis Holiday market

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.
Entertainment at the Annapolis Holiday Market
Thursday
4 pm to 10 pm Live music from the Naval Academy Primary School Chorus and oyster ornament decorating with Chesapeake Family Media
Friday
11am to 9pm DJ Jessie is spinning holiday tunes
4 pm to 8 pm Jolly Express Cruise departs hourly
7pm Holiday Candlelight Stroll in historic Annapolis
Saturday
11 am to 6pm - Live music by Priddy Music Academy bands
530pm - 830 pm - Fundraiser on the Harbor Queen for We Care and Friends
6 pm to 8 pm - It's the Eastport Yacht Club Lights Parade
Sunday
4 pm to 7 pm Jolly Express Cruise departs hourly
11 am to 5 pm - Live music by Priddy Music Academy bands
Entertainment in downtown Annapolis near the Annapolis Holiday Market
Thursday
4 pm to midnight -It's the Midnight Madness Shopping event all through downtown Annapolis
8 pm Peter Mayer: Stars & Promises Christmas Tour
Rams Head On Stage
Friday
6 pm Celebration of Christmas Concert
Maryland Hall
7 pm Holiday Candlelight Stroll
Watermark Tours Charters Cruises
830 pm Carbon Leaf Concert
Rams Head On Stage
Saturday
3pm Tuba Christmas outdoor concert on Church Circle
St Annes Church
3 pm & 830 pm Carbon Leaf Concert
Rams Head On Stage
415 pm Lights Parade Holiday Package
Watermark Tours Charters Cruises
Sunday
1pm Carbon Leaf Concert
Rams Head On Stage
730pm Pam Tillis: “Belles & Bows” Country Hits & Christmas Favorites
Rams Head On Stage
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.