What to expect at Midnight Madness 🌙
If you’re looking for a unique holiday experience in Annapolis and Anne Arundel County, Midnight Madness should be at the top of your list! But what exactly is it?
Midnight Madness is a fun, festive shopping event that happens during the holiday season. Local shops, boutiques, and galleries stay open late—sometimes until midnight! Offering special deals, holiday treats, and unique experiences you won’t find during regular hours. It is a magical mix of holiday shopping, community, and festive entertainment. Midnight Madness will occur December 4, 11, and 18, 2025.
Shop-aholics, this is for you!
It’s the perfect chance to cross off your gift list while enjoying the cozy, festive energy of the city. From unique boutique gifts tucked into historic storefronts to pop-up artisan vendors lining the streets, there’s something special waiting on every corner.
Pet Alpacas & Unexpected Surprises 🦙
Only in Annapolis could your evening include petting alpacas right in front of the Alpaca International Store on Main Street. These fluffy friends add a touch of whimsy and make for the perfect holiday photo op.
Sip Spiced Tea & Enjoy the Music 🍵
As you wander, grab a cup of spiked tea from The Spice & Tea Exchange on Main Street. The warm, festive flavors pair perfectly with the sounds of carolers on various streets, singing your favorite Christmas jingles.
Hot Chocolate & Cozy Atmosphere 🍫
Feeling chilly? Head over to West Street for creamy hot chocolate or other seasonal treats. On Thursday, December 4th, be sure to stop inside the Visitor Center at 26 West Street for delectable s’mores! Stroll past creative and artsy vendors offering handmade ornaments, art, and unique gifts.
Snowflake Alley❄️
A whimsical alley (Cabbage Alley) is lit with twinkling snowflakes, making it a perfect backdrop for holiday posts. Everyone wants a photo here.
Festive Dining 🍴
When hunger strikes, step inside cozy restaurants or hidden speakeasies for a warm, festive dinner atmosphere. Whether you’re enjoying local flavors, seasonal cocktails, or intimate décor, these spots are perfect for soaking in the holiday spirit.
In Annapolis, Midnight Madness usually takes place on select Thursdays in December, right in the heart of downtown. Shops, galleries, and restaurants open late, giving you plenty of time to explore without feeling rushed.
