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Tipsy Teacher Volunteer Squad

Annapolis Midnight Madness

Created by Tipsy Teacher Volunteer Squad Contact

The first two Thursdays of December from 4 pm until Midnight and the third Thursday of December from 4 pm until 11 pm

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 11, 2025 at 04:00 pm to 11:55 pm - Eastern Time (US & Canada)

Main Street, West Street, Maryland Avenue, State Circle, Market Space, and Dock Street, Maryland Avenue & State Circle Merchants, State Circle, Annapolis, MD, USA
View on Map

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

  • Pour Wine
    2 spots available

06:45 pm - 10:00 pm - Eastern Time (US & Canada)

  • Pour wine
    2 spots available

09:45 pm - 11:55 pm - Eastern Time (US & Canada)

  • Pour Wine
    2 spots available

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