🎄 Midnight Madness Schedule 12/18/2025

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🎄4:30 pm – 12:00 Midnight Midnight Madness w/ Downtown Annapolis Partnership at Annapolis

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5-6 pm Baby Alpacas at Alpaca International

🎄 5-7 pm Jefferson Holland of Poet Laureate for the City of Annapolis at Local by Design Downtown Annapolis  - Maryland Ave - Annapolis

5-11 pm Annapolis Police Department Presents a Holiday Movie : Elf on Francis Street 

5:30-9:30 pm Classic Theatre of Maryland : Caroling in the courtyard at Reynolds Tavern in Annapolis – Annapolis

6-7 pm Apex Arts of Bates Middle School of Anne Arundel County Public Schools (AACPS) by HOBO 

6-7 pm Annapolis Elementary School of Anne Arundel County Public Schools (AACPS) by HOBO 

🎄6-9 pm Priddy Music Academy at Christmas Tree

🎄 6-9 pm Michael K of Pretty Big Deal - Michael K : inside for Midnight Madness sing along at Middleton Tavern – Annapolis

6-9 Design In Motion Dance Studio at Zachary's Jewelers

🎄 6-10 pm Guava Jelly  : Midnight Madness in front of Visit Annapolis  West Street - Annapolis

🎄 6-11 pm Musicians TBA : Midnight Madness at Capistrano Barbershop - Annapolis

🎄 7 pm Painted Trillium by Red Red Wine Bar + Bistro - Annapolis

7-8 pm Typhrodisia's Bellydance and Beyond Studio  at Alpaca International

🎄 7-9 pm Wendell Live - Sinatra Tribute Artist  : Midnight Madness at Annapolis Collection Gallery  West Street – Annapolis

7-9 pm Compass Rose Theater at Historic Maryland Inn of Historic Inns of Annapolis  - Main Street - Annapolis

🎄 7-10 pm Michael Waskey Music at Blanca Flor Silver Jewelry  - Market Space - Annapolis

🎄 7-11 pm DJ Deezy : Midnight Madness at Parley Room- Annapolis

8-9 pm Annapolis Salvation Army Band  by Zachary's Jewelers - - Market Space - Annapolis

🎄 9:30 DJ Jay Crawdads: Midnight Madness at Red Red Wine Bar + Bistro- Annapolis

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Carolers & Sons of the Severn Chorus  throughout the night up and down Main St and Maryland Avenue and State Circle Association