What Is Midnight Madness in Annapolis?
Midnight Madness is a late-night holiday shopping event in downtown Annapolis designed to bring locals and visitors together for an evening of shopping, dining, entertainment and holiday fun.
Participating businesses throughout downtown open their doors late, giving you more time to browse locally owned boutiques, enjoy free delicious samples, discover unique gifts, pick up something special for yourself and experience the charm of Annapolis after dark.
The event stretches through some of downtown’s most iconic streets, including Main Street, West Street, Maryland Avenue, State Circle, Market Space and Dock Street. Festive decorations, lights, trees, garlands, snowflakes and bows help turn the historic district into a glowing holiday escape.
When Is Midnight Madness?
Mark your calendar for three festive Thursday nights:
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Thursday, December 3, 2026
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Thursday, December 10, 2026
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Thursday, December 17, 2026
Individual businesses may have their own hours, specials and activities, so be sure to check with your favorite shops before visiting. As always view https://www.annapolis.gov/ for official and most up to date information.
Shop Small & Find Something Wonderful
If your holiday shopping list is starting to look a little intimidating, Midnight Madness is your sign to head downtown. Check off your holiday shopping list while exploring downtown Annapolis boutiques filled with unique gifts, jewelry, clothing, local art, and Chesapeake-inspired treasures.
Follow the Lights & Holiday Cheer
Downtown Annapolis shines a little brighter during Midnight Madness! Enjoy twinkling lights, live music, carolers, festive entertainment, and holiday surprises along the way.
Make a Night of It
Start with dinner, shop local, grab a sweet treat, and soak up the holiday atmosphere. Make it a festive date night, family outing, or evening with friends. Stay at a cozy hotel or Bed and Breakfast if you're wanting more of Annapolis and Anne Arundel County.
Experience a Maryland Holiday Tradition
From glowing storefronts to historic streets filled with holiday cheer, Midnight Madness is a beloved Annapolis tradition worth experiencing this December.
