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: Thursday, December 3, 2026, Thursday, December 10, 2026, and 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.

Midnight Madness at the Visitor Center

You'll want to make a stop at the Visitor Center on 26 West Street and here's why...

On the first night of Midnight Madness warm up with complimentary hot cocoa while shopping for festive ornaments from Pearl's Gallery pop-up shop. The second night is all about sweet treats and  self-care! Enjoy complimentary s'mores and a little holiday pampering with free massages and permanent jewelry from Even Keel Wellness Spa. For the third and final night we're bringing back s'mores again and Eesh's Pieces will be selling cookies. Visit us from 5:00 p.m. - 8:00 p.m. on December 3, 10, and 17 for a little holiday merriment while exploring Downtown Annapolis.

Shop Small with Midnight Madness Deals!

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.

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.