If you’re looking for a holiday experience that feels like stepping straight into a snow globe someone shook a little too enthusiastically, downtown Annapolis is about to become your happy place. Midnight Madness is sweeping in again on December 4, 11, and 18, turning three Thursdays into an extravagant, cinnamon-scented marathon of twinkle lights and impulse purchases you will absolutely justify later.
Think twinkling canopies of lights stretching over West Street and Maryland Avenue, a 25-foot Christmas tree glowing in Market Space, wreaths everywhere, and storefront windows dressed so elegantly they could walk a red carpet. Snowflake Alley (that charming, twinkly passage off Main Street) is back too, ready to become the backdrop of half the county’s holiday photos. And yes, the alpacas will once again be stationed at the top of Main Street, posing like they absolutely know the camera loves them.
Shops, galleries, and restaurants will stay open late (midnight on the Dec. 4 and 11, and until 11 PM on Dec. 18) offering deals, treats, and the kind of friendly service that makes you forget holiday shopping can be stressful.
New businesses are joining the fun this year, like Local Coast and Abby Adams Boutique, so don’t be surprised if you wander into a store you’ve never seen and emerge moments later wondering how three scented candles, a scarf, and a jar of locally made something-or-other ended up in your hands. It’s holiday magic. Just accept it.
While you wander, follow your nose. There’s free spiced tea at The Spice & Tea Exchange on Main Street, warm, fragrant, and exactly what your hands want to wrap around on a chilly night. Over on West Street, hot chocolate and seasonal treats will be available or head inside the Visitor Center at 26 West Street for s’mores that will give you the sugar-fueled rush to continue shopping until midnight.
Entertainment pops up everywhere: guitars, choirs and carolers, and the kind of street-corner surprises that gives Midnight Madness all the small town vibes. On top of that, each week features bonus events:
- December 4: The Mayor’s Open House at City Hall at 4:30 PM
- December 11: West Street Holiday Market, full of handmade gifts and local vendors.
- December 18: The Annapolis Holiday Market on the front lawn of St. John’s College, a perfect final stop on the Eleventh Hour.
And because Annapolis understands that nothing ruins festive cheer faster than parking stress, the city goes all out with perks. You can park free at the Calvert Street Garage (19 St. Johns Street) from 6 PM to 6 AM. The Whitmore Garage (25 Clay Street) offers a flat $2 rate starting at 4 PM. The Hillman Garage gives you your first hour free with ParkMobile, and commercial streets offer two hours free if you start your session on the app. Plus, free shuttles, including the electric Current Trolley and the Circulator Bus, will ferry you between garages and the downtown festivities.
Between the lights, the music, the cocoa, the alpacas, and the last-minute deals you absolutely earned, Midnight Madness is Annapolis at its most magical and you will not want to miss a minute of it.
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