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Midnight Madness—A Must-attend Annapolis Tradition

With the triple holiday season shopping whammy of Black Friday, Small Business Saturday and Cyber Monday behind us, you might already be done shopping. But that’s no reason not to head to Midnight Madness.

In fact, this Annapolitan, who’s attended each Midnight Madness since he could walk, guarantees that there are always more unexpected gifts to discover, and more memories to make in downtown Annapolis on Thursday nights in December.

Here are 10 things—one for each of Santa’s reindeer, plus one for good luck—that you won’t want to miss on December 5, 12, and 19:

1. OG Decorations
As always, virtually every street, storefront and store interior will be festooned with garlands, wreaths, bows, and lights galore. From twinkling stars hanging over West Street, Maryland Ave., and super-selfie-site Snowflake Alley, to the always-amazing seasonal window display at A.L. Goodies and well-lit Ego Alley boats, they’ll give visitors of all ages the holiday feels.

2. Home Decorations
Wherever your journey takes you, it will inevitably include getting to see candles and Christmas trees in the windows of many of the beautiful historic homes surrounding downtown, from the Governor’s Mansion and Paca House to the cozy colonial townhouses on Cornhill and Conduit streets.

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3. The Market Space Christmas Tree
In the last of our “decorations to see” entries, you don’t want to miss checking out downtown’s official tree, illuminated on December 1 and is selfie-friendly as usual.


As always, downtown shoppers can receive three hours of free parking at metered parking spaces but, unlike in past years, they will need to download and use the ParkMobile app (available on iOS and Android) and enter “ParkDTA” to do so. 

Another option is to take advantage of the two FREE Circulator buses that will run from 4 p.m. to midnight on a route from Park Place to West Street, State Garage, State Circle, Church Circle, Duke of Gloucester, City Dock, and Main Street. You can track its real-time location by downloading the RLS Shuttle app on your smartphone and selecting “Annapolis.”

4. The Red Kettle
Like thousands of other cities across the country, downtown Annapolis is home to a Salvation Army kettle each holiday season. You’ll know how to find it by hearing the sounds coming from its volunteer bell-ringer, and letting your kid drop in some coins, as I did as a little one and still do now, provides a great opportunity for an early-childhood lesson in philanthropy.

5. Music Galore
While there’s no “official schedule” of who will play or sing what when, the Salvation Army Band, professional choral groups, and school choruses will be providing holiday vibes all night—not to mention the all-holiday soundtracks playing in each store and the many members of the general public, like me, who can’t resist joining in or, at the very least, doing some heavy humming.

  • 6. Adult- and Kid-Friendly Libations and Bites
    Virtually every store will have something to satisfy your stomach, whatever your pickiness level or age. As long as you leave some for me, my top highlights include:
  • A full spread of cheeses you might not be able to pronounce and wines you might not be able to resist at 26-year-old downtown mainstay The Big Cheese
  • Endless samples at my three year-round go-tos, Seasons Olive Oil & Vinegar Taproom, where I highly recommend asking about the “Wild West” that is olive oil labeling regulations; The Spice & Tea Exchange, where I can confidently say I’ve spent at least 50 cumulative hours opening and smelling diverse spices, salts, sugars, and teas; and Annabeth’s, where there are always plenty of unique snacks and a new craft beer in-keg to try.

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7. Store-Specific Photo Opps
As in most years, Alpaca International will have an alpaca to pose with and (if you’re so inclined) pet so that you can feel the fiber that the store’s owner says was once reserved exclusively for Incan kings and queens. I also learned that 41-year-old Hats in the Belfry will not only be encouraging adults to try on and take photos with as many hats as they desire, but will also have a family- and kid-friendly selfie station, including props, in its front window.

8. People- and Pet-Watching
It probably goes without saying, but Midnight Madness draws quite a diverse crowd. From the fancily dressed bourgeoisie and colonial reenactors to seasonably inspired holiday enthusiasts and pets, many of whom often have Christmas lights around their necks, there’s no shortage of sights. Word on the street is that there will be at least one Santa roaming the town as well!

IMG 3274 copy9. One-Night Only Deals
Whether you’re planning to shop or not, many, if not most stores will be offering deals beyond any other seasonal specials. Hatley, for example—a store with kids’ clothing so cute even this uncle on a budget has bought multiple gifts there—will be offering a storewide special on all three nights (keep your eye on the store’s social media!), while The Black Dog will not only be offering free balloons to all kiddos but a free branded tote bag to anyone who spends $100 or more. As Kayley Summerfelt, the store’s manager, told me (and I completely agree), Midnight Madness is all about “having a fun and festive shopping experience (unlike most mall shopping trips, she added) and discovering one-of-a-kind things while showing your support for businesses that are actually part of your community.”

10. New Stores
Downtown’s newest store, Surf’s Up Candles, has an awesome atmosphere (and amazing smells) that people of all ages will love, while Mango + Main, another newcomer on Maryland Ave., has unique, artisan-made, 100% fair-trade fashion and home décor (much of it quite appropriate for stocking stuffers!) that owner Shannon Riesenfeld can’t wait to share with guests.

With so many things to see and do, it’s clear that Midnight Madness is something you and your family will be glad you didn’t take for granted.

—Steve Adams

Find more holiday fun and revelry at our Holiday Countdown and our Holiday Happenings pages, where you can find all of the best holiday fun in the area!



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