Holiday lights on West Street in Annapolis.
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Midnight madness, Parade of Lights. Annapolis Events and Holiday Festivities

With snowflakes beginning to fall and a crisp winter breeze blowing in from the Severn River, the holiday scene in Annapolis is festive and pulled right out of A Christmas Carol by Charles Dickens. From classic Annapolis events like the Parade of Lights to the cherished Midnight Madness local shopping extravaganza and holiday-themed markets, the downtown district comes alive with wintry cheer over the weeks between Thanksgiving and Christmas.

When you stay at our Annapolis bed and breakfast, you will be in the center of all the merriment, perfect for shopping, enjoying the festive atmosphere, and one-of-a-kind Parade of Lights.

Lighting the Ceremonial Christmas Tree

The official start to the holiday season kicks off on Thanksgiving weekend with the “Grand Illumination” lighting of the Christmas tree at the City Dock. The tree’s thousands of lights turn on, carolers fill the evening air with song, and the countdown to Christmas begins. The tree stays lit throughout December, so whenever you visit, make a point to stop by and snap a family picture in front of the glimmering tree as you take a stroll by the picturesque harbor.

christmas balls on a tree

Candlelight Tour

Another beloved tradition, an evening Candlelight Tour, kicks off the same weekend, taking place every Friday and Saturday through late December from 7-8:30 pm. Much more interesting than just a dry recitation of Annapolis facts, your tour guide will interpret our city’s  history, bringing it to life in an engaging, witty, and theatrical way, as if you were chatting with an Annapolis resident from centuries ago. It’s similar to other excellent Annapolis walking tours, but the Candlelight Tours take place at night along enchantingly lit lanes and feature holiday themes. The tours begin at 188 Main St, right across from Joss Cafe and Sushi Bar, which has been serving sushi for over 30 years and is one of our favorite restaurants within walking distance. Warm up before your walking tour with some sake and pan-fried dumplings, followed by some of their 40+ sushi rolls (for an extra kick, try one of their specialty rolls, like the Salmon Jalapeno).

Chocolate Binge Festival 

The holiday-themed Annapolis events keep rolling on the first weekend of December, with the Chocolate Binge Festival on December 3rd, 2023. From 11 am until 4 pm, West St (one of the main thoroughfares leading out from St. Anne’s Parish, over 300 years old and a monument to Annapolis history) becomes a chocolate lover’s dream. Whether your sweet tooth trends more towards truffles, fudge, or macaroons, you’ll find it all and more as you browse and sample the chocolate vendors set up along West St. It all culminates with the 5 pm ceremonial illumination of the West St holiday lights, strung up beautifully over the quaint brick-lined sidewalks and colonial-era storefronts.

Midnight Madness and the Annapolis Holiday Market

In what has become a beloved holiday tradition, Midnight Madness adds some after-dark fun to the walkable streets of Annapolis’s historic district. On three consecutive Thursdays in December of 2023 (12/7, 12/14, and 12/21), the city collaborates to decorate several main streets downtown (Main St, West St, Maryland Ave, State Circle, Market Space, and Dock St) with wreaths, gorgeous light displays, and bright red bows, while musicians and carolers provide entertainment. In addition to creating a festive and lively ambiance, the event aims to support our local businesses (among the rows of downtown shops, you’ll find hip clothing boutiques, countless art galleries, and charming bookstores), who keep their doors open late until midnight. Don’t miss checking out unique Midnight Madness locations like the Snowflake Alley, which transforms Cabbage Alley between Main and Francis St into a wintry and magical walkway.

Coinciding with the first night of March Madness, Dec 7th, you’ll have even more shopping options at the Annapolis Holiday Market, one of the newer Annapolis events, celebrating its 2nd year in 2023. From 5-9 pm, over 80 local artisans will be set up along City Dock by the waterfront (be sure to check out the lit-up Christmas Tree while you’re down there). Whether it’s handmade jewelry, art, local honey and coffee, or stocking stuffers like specialty dog treats, you’ll directly support local artisans and find that perfect holiday gift in one festive outing.

Annapolis Harbor Aglow and Lights on the Water

Although the Macy’s Thanksgiving parade gets all the glamor and media attention, our Parade of Lights is undoubtedly one of the most unique holiday parades you’ll see anywhere. Put on by the Eastport Yacht Club and a team of volunteers who endearingly call themselves “parade elves,” the event celebrates its 41st year in 2023 after being canceled recently in 2020 and 2021. 

The “parade on the water” started with just one boat decorated with lights in the early ‘80s, growing over the decades to its current massive size, with everything from tiny sailboats to 70-foot vessels lit up with bright and creative light displays. Thousands of people will line the harbor from 6-8 pm on December 9th, 2023, and the nearby bridge over Spa Creek (a great vantage point from above) to marvel at the ingeniously decorated boats – you may see a mast lit up as a sparkling palm tree, the Grinch taking over a boat’s deck, or a sailboat transformed into Santa’s sleigh.

annapolis harbor

After the parade festivities wind down, head back to the Annapolis Holiday Market for more holiday shopping and grab a bite from the local food vendors set up by the water on Dock St. Finish the evening with some live music and a specialty cocktail or mug of beer at the Federal House Bar and Grille, located just a couple of blocks away. Like most places in Annapolis, the Federal House’s historic charm is palpable, tracing its pub roots back to 1830.

Stay with us and experience the magic of holiday traditions, new and old, in Annapolis!