Celebrate a Magical Christmas in Annapolis and Anne Arundel County

The Grand Illumination with annual tree lighting in downtown Annapolis.

Magical! That’s the word that best describes Annapolis during the holiday season. Green garlands, red ribbons, and white lights adorn the fronts of shop after shop, business after business in the Downtown Historic District making the city look and feel more than ever like a quaint 18th-century European town that’s counting down to Christmas. A spirit of joy and anticipation fills the air from the moment the city’s Christmas tree lights up on December 1. The Grand Illumination kicks off a month of activities that culminates with a New Year’s Eve celebration that features afternoon activities for the kids and wraps up with live music and midnight fireworks at City Dock.

From beginning to end, December in Annapolis is synonymous with treasured memories of family fun and romantic getaways. Back for its fifth year, the December 8 Chocolate Binge Festival includes more than 40 local chocolate vendors serving up great stocking stuffers – if the chocolate hangs around that long!

Midnight Madness populates the streets of Annapolis with music, dancing, and feasting.

Midnight Madness is another treasured holiday tradition. Amidst music and dancing in the streets, shoppers make their way from store to store in a moveable feast that lasts until midnight the first three Thursdays in December. Mission accomplished, many satisfied gift givers treat themselves to an overnight stay in downtown Annapolis. Elsewhere on the shopping scene, a December 7 Fire and Ice Festival at the nearby Annapolis Towne Centre promises fun for all.  

West Annapolis will host its second annual Winterfest and European Christmas Market December 7-8 and 14-15. Fifty fine arts vendors will sell their gift-worthy crafts from custom-made, European-style stalls positioned around a central gathering space filled with firepits, food and drink trucks, and plenty of glühwein to go around!

The Military Bowl parade brings the beloved Budweiser Clydesdales to town.

West Annapolis will be front and center again on December 26 during an 11:00 a.m. until 5:00 p.m. Miracle on Annapolis Street celebration featuring the famous Budweiser Clydesdale horses. The horses will travel through West Annapolis for visitors to see up close and personal from 1:00 p.m. until 3:00 p.m. The celebration serves as a pre-game pep rally for the Military Bowl that will take place at Navy-Marine Corps Memorial Stadium the following day. As a prelude to the 12th anniversary game, the Clydesdales will appear in a December 27 Military Bowl Parade through downtown Annapolis. The noon game matches a team from the Atlantic Coast Conference against an opponent from the American Athletic Conference.  

City Dock’s the place to be on December 14 when up to 40 brightly lit sail and powerboats bedecked with thousands of holiday lights parade around the Annapolis waterfront and Spa Creek in the 37th Eastport Yacht Club Lights Parade. When the parade is through, stroll through the downtown Historic District taking in the timeless decorations that adorn centuries-old homes and businesses. If you prefer, let Watermark’s experts take you on a Holiday Candlelight Stroll of the nooks and crannies of Annapolis on select Friday and Saturday evenings in December. Or, hop aboard Watermark’s Jolly Express for a cruise aboard the antler-bedecked Miss Anne Friday-Sundays throughout December.

The Eastport Yacht Club Lights Parade dazzles waterfront revelers.

The holidays are a perfect time to see two of Annapolis’ five-part Georgian mansions in all their holiday grandeur – during historic Hammond-Harwood House’s Holiday Open House and Greens Sale on December 6 and Historic Annapolis’ open house at the 18th-century home of Declaration of Independence signer William Paca on December 7.

Annapolis by Candlelight allows visitors to enjoy some of downtown’s finest dwellings.

There’s plenty going on in November to give you a head start on the holidays. Thankstival at the Anne Arundel County Fairgrounds on November 2 will feature live music, food, fun and a host of artisan gifts to choose from. With its 130 vendors, the November 3 First Sunday Arts Festival on West Street in Annapolis could easily serve as a one-stop shop for forward thinking Santas. Now in its 28th year, Historic Annapolis’ November 8-9 Annapolis by Candlelight provides an inside peak at some of the finest homes in downtown Annapolis, and Small Business Saturday on November 23 is the perfect time to patronize mom and pop businesses so vital to Annapolis and Anne Arundel County’s economy.

A brilliant drive-through display of holiday lights can be found at Sandy Point State Park starting in late November.

Lovers of holiday lights can get their fix at Lights on the Bay at Sandy Point State Park from November 23 through January 1. The drive-through holiday lights show beside the Chesapeake Bay features more than 70 animated and stationary displays.

The yearlong wait is over! It’s time to dive into Annapolis and Anne Arundel County’s holiday magic! To find out more, visit https://www.visitannapolis.org/.