Midnight Madness Annapolis

Experience the Magic of Midnight Madness

The holiday season is upon us, and what better way to embrace the festive spirit than with Midnight Madness, a beloved Annapolis tradition that transforms downtown into a sparkling winter wonderland. On December 5th and 12th from 4:00 PM to midnight, and again on December 19th for the Eleventh Hour until 11:00 PM, the charming streets of Annapolis will come alive with holiday cheer, late-night shopping, and community celebration.

A Downtown Winter Wonderland

Step into the heart of Annapolis and be transported to a scene straight out of a Norman Rockwell painting or a Charles Dickens novel. The streets of Main Street, West Street, Maryland Avenue, State Circle, Market Space, and City Dock will be adorned with twinkling lights, festive garlands, and holiday trees. Enjoy the glow of decorated storefronts, garland-lined lampposts, wreaths, and even a whimsical Snowflake Alley.

Annapolis doesn’t stop at decorations; on-street entertainment fills the air with music, laughter, and the warmth of the season. Live performances, carolers, and festive surprises will keep visitors entertained as they stroll through the city.

Shop Local and Celebrate Community

Midnight Madness is more than just a shopping event; it’s about celebrating the heart of Annapolis—its local businesses and tight-knit community. Over 90 stores and 80 restaurants will stay open late, offering special holiday discounts, treats, and seasonal displays to help you find the perfect gifts. From boutique shops and artisan galleries to cozy cafes and award-winning restaurants, there’s something for everyone. Whether you’re picking out handmade jewelry, a unique piece of art, or a festive outfit, shopping local means giving back to the community and supporting small businesses.

Free Parking and Easy Access

Getting around downtown during Midnight Madness is a breeze with convenient parking and transportation options:

• Free Parking: Calvert Street Parking Garage (19 St. Johns Street) from 6 PM to 6 AM.
• Discounted Parking: $2 all-night parking at Whitmore Garage (25 Clay Street) from 4 PM to 6 AM.
• Free Circulator Bus: Hop on the circulator bus for easy access to Park Place and Knighton garages.
• Short-Term Free Parking: On-street meters on commercial streets are free for up to two hours when using the ParkMobile app.

Bring Friends and Family

Midnight Madness isn’t just for shoppers—it’s a festive outing for friends, families, and visitors looking to soak up the magic of the holidays. Enjoy live music, explore beautifully decorated shops, and make memories that will last all season long.

Why Annapolis is a Top Christmas Town

Recognized as one of the nation’s Top 10 Christmas Towns, Annapolis offers the perfect blend of historic charm and modern festivities. Midnight Madness encapsulates that magic, bringing together community, tradition, and holiday joy under twinkling lights.

Mark Your Calendar:

• December 5th & 12th: 4:00 PM to Midnight
• December 19th (Eleventh Hour): 4:00 PM to 11:00 PM

Come for the shopping, stay for the charm. Midnight Madness in downtown Annapolis is your opportunity to rediscover the joy of the season, support local businesses, and create magical holiday memories.

For more details on Midnight Madness, parking, lodging, and other events, visit the Downtown Annapolis Partnership. See you under the holiday lights!