Downtown Annapolis hosts Midnight Madness holiday shopping spree

WTOP's Jason Fraley previews Midnight Madness in Annapolis (Part 1)

The Maryland state capital has been busy facing health and economic concerns during the COVID-19 pandemic, a juggling act that kicks into high gear this holiday season.

This week, Annapolis hosts the Midnight Madness holiday shopping spree on Dec. 3 and Dec. 10 from 4 p.m. to midnight, as well as on Dec. 17 from 4 p.m. to 11 p.m.

“This is a tradition that has happened for a long time in Annapolis,” Erik Evans, executive director of the Downtown Annapolis Partnership, told WTOP. “It’s a fun evening where locals come out and shop locally and support our local businesses — and this is the best time to visit Annapolis because all the holiday decorations are up.”

The corridors of West Street, Maryland Avenue, Main Street and the City Dock area will be filled with holiday decorations, window displays, garland, wreaths, holiday lights, a snowflake alley, light canopies, a large Christmas tree and a menorah.

“You can see a 20-foot Christmas tree that’s in honor of the Naval Academy’s 175th anniversary,” Evans said. “You’ll see multiple Christmas trees. The streets are lined with holiday greens and wreaths. The shop windows are gorgeous. It’s just a fun night to come out and shop in many of the unique stores we have in Annapolis.”

Downtown Annapolis boasts roughly 90 shops for you to browse for gifts.

“There’s a lot of unique, small, locally-owned businesses here,” Evans said. “We have Annapolis Pottery, Local By Design, Annapolis Collection Gallery, the Annapolis Arts Alliance has a new gallery at 57 West Street. … We’ve got art galleries, antique stores, gift shops, jewelry stores like Zachary’s Jewelers that everybody loves.”

If shopping works up your appetite, various restaurants will be open at limited capacity.

“You’ve got Milton’s Tavern, Market House, Red Red Wine Bar, Rams Head, 49 West Coffee House, Galway Bay, there’s just a wide range of restaurants that you can enjoy,” Evans said. “We have a ton of restaurants that have outdoor dining that have put up tents or heaters or both. We even have some igloos for small groups.”

Make sure you follow the state’s COVID-19 protocols while dining and shopping.

“We definitely want everyone to wear a mask,” Evans said. “We’ll have hand sanitizer at all the stores for you to wash your hands frequently. Stores do have a limit of 50% occupancy, and we encourage you to social distance while you’re there. … We’re not going to do the [street] entertainment or the food and wine this year due to COVID.”

It’s all a way to try to save businesses through the holidays and the pandemic.

“Tourism is way down,” Evans said. “The Naval Academy is on lockdown for the public, St. John’s College went virtual … and most [government employees] are working from home, so foot traffic is way down this year. The holidays are make or break time for retail. We would love to see all of our retail make it through holidays and through COVID.”

Free parking garage options include select hours at Knighton Parking Garage, Gotts Court Parking Garage, Calvert Street Parking Garage and Hillman Parking Garage.

“It’s been a tough year for everybody,” Evans said. “There’s nothing like getting outdoors, getting some exercise, doing some window shopping, seeing beautiful decorations to lift your family’s spirits. I encourage you to get out, lift your spirits and visit Annapolis.”

WTOP's Jason Fraley previews Midnight Madness in Annapolis (Part 2)

Listen to our full conversation here.

Jason Fraley

Hailed by The Washington Post for “his savantlike ability to name every Best Picture winner in history," Jason Fraley began at WTOP as Morning Drive Writer in 2008, film critic in 2011 and Entertainment Editor in 2014, providing daily arts coverage on-air and online.

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