You may not think of Annapolis as a your ideal wintry retreat this season, but according to Travel + Leisure Magazine, Annapolis is one of America's Best Towns for the Holidays. This holiday season promises to be no different. Whether you want to wander around town taking in the quiet of the season, looking for shopping options, or seeking out something exciting to do, it’s in Annapolis this December.

Chocolate Binge Festival

Annapolis this December

Everyone loves chocolate and Annapolis' will be celebrating by filling West street with local chocolate vendors ready to help chocoholics get through the holiday season. On Sunday December 2 from noon to 5:00 p.m. on the first blocks of West Street will be the 4th annual Annapolis Chocolate Binge Festival, featuring family friendly entertainment, chocolate, holiday shopping and the lighting of the West Street Holiday Light Canopy.

The event is free, but donations are greatly appreciated, benefiting organizations like the Annapolis Arts District and We Care and Friends.

Midnight Madness 

Annapolis this December

Don't miss Midnight Madness (Thursdays, December 6 and  13 from 6:00 p.m. until Midnight and December 20 from 6:00 p.m. to 11:00 p.m.) where select stores in downtown Annapolis will remain open until midnight giving bargain-hunters and last-minute shoppers an excuse to get out and shop well into the night. It's also the perfect excuse to catch up with friends and take advantage of special deals in the middle of holiday fun with a Girls' Weekend. So, come enjoy the spirit of Annapolis as the town will be inundated with live music, holiday entertainment and cheer throughout the night.

So, come enjoy the spirit of Annapolis as the town will be inundated with live music, holiday entertainment and cheer throughout the night. Main Street, State Circle/Maryland Avenue, and the Arts District in search of that perfect gift.

Visit the Downtown Annapolis Partnership online for updates this holiday season.

Eastport Yacht Club Lights Parade

Each December, a truly Annapolitan event takes place: The Eastport Yacht Club Lights Parade. Seeing as Annapolis has been dubbed the Sailing Capital of the U.S., it comes as no surprise that the city would celebrate the holidays by taking to the water. During the event, dozens of boats can be seen floating through Spa Creek and Ego Alley illuminated with thousands of colored lights and crewed by jolly revelers. Prime viewing areas include: Eastport, Spa Creek, City Dock and the Naval Academy sea wall. The free event kicks off on December 8, lasting from 6:00 p.m. to 8:00 p.m. Be sure to click here for more information and to meet the winner of last year's light parade.

Lights on the Bay

A county favorite for families, Lights on the Bay is the perfect way to get in the holiday spirit this December. The drive-through light show features more than 60 animated and stationary holiday displays, all set against the Chesapeake Bay in Sandy Point State Park. The display is open every night (weather permitting) from November 18 to January 1, 5:00 p.m. to 10:00 p.m. Tickets are $15 per car.

The Military Bowl presented by Northrop Grumman

The Military Bowl presented by Northrop Grumman (December 31 with kickoff at noon) is one of the most anticipated events of the year. Pinning the ACC and AAC conference champions against each other, the Military Bowl is the perfect way for football fans to end the college season. The morning of the game is one of Annapolis' newest traditions: The Military Bowl Parade, featuring The Budweiser Clydesdales. Beginning at 11 a.m., they will lead the parade line - along with Medal of Honor recipients, mascots, and team bands - from City Dock in downtown Annapolis to the Navy-Marine Corps Memorial Stadium as part of the many special events throughout the day.

The best part of this year's Military Bowl? The party is just getting started once the game ends!

New Year’s Eve Celebrations

Welcome in 2019 after the game at City Dock in downtown Annapolis. Grab your friends or the whole family for a night filled with entertainment, food, and fireworks displays in the Annapolis Harbor as the clock strikes 12. Enjoy family-friendly music early in the evening before heading to the waterfront for a view of the fireworks, or celebrate the New Year in one of the city's many pubs and bars. It's all free and everyone is invited! Cruises on the Bay by Watermark even offers the perfect way to bring in 2018 with their New Year’s Eve Fireworks Cruise in the Annapolis Harbor.


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