Tipsy Teacher Volunteer Squad

Annapolis Midnight Madness

Created by Tipsy Teacher Volunteer Squad Contact

A Festive Shopping Time in Downtown Annapolis

Downtown Annapolis Partnership proudly presents Midnight Madness—a Historic Downtown Annapolis holiday tradition that encompasses the charm and character of our most beloved memories of Norman Rockwell and Charles Dickens. We will adorn the streets and participating storefronts with holiday decorations, trees, garlands, snowflakes, bows, and lights to create a Downtown Winter Wonderland and free on-the-street entertainment.

Dates and locations

Thursday, December 18, 2025 at 04:00 pm to 11:00 pm - Eastern Time (US & Canada)

Main Street, West Street, Maryland Avenue, State Circle, Market Space, Maryland Avenue & State Circle Merchants, State Circle, Annapolis, MD, USA

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Volunteer here! Feel free to sign up for multiple time slots. Please provide full name and contact information for each volunteer. Contact Jess if you are unable to make it or running late.410-271-8914

03:45 pm - 07:00 pm - Eastern Time (US & Canada)

Pour Wine/ Take pictures

2 spots available
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06:45 pm - 11:00 pm - Eastern Time (US & Canada)

Pour Wine/ take pictures

2 spots available
-+

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