Written by on December 01, 2017

6 Ways to Explore Annapolis this December

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.

Midnight Madness 

Don’t miss Midnight Madness (Thursdays, December 7 and  14 from 6:00 p.m. until Midnight and December 21 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.

Chocolate Binge Festival

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 3rd from noon to 5:00 p.m. on the first blocks of West Street will be the 3rd 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.

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 9th, lasting from 6:00 p.m. to 8:00 p.m.

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 22nd to January 1st, 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 28th with kickoff at 1:30 p.m.) 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 Official Military Bowl Tailgate kicks off in the Blue Lot on the west side of Navy-Marine Corps Memorial Stadium. Opening at 9 a.m., admission to the tailgate is free and will feature music, games, food & beverages from fantastic Annapolis restaurants, and exciting giveaways for the first arrivals! Get your tickets in advance by clicking here.

New Year’s Eve Celebrations

Welcome in 2018 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.


Photos courtesy on VisitAnnapolis.org

Whether you’re looking for things to explore in the area, the latest news and updates on the area’s thriving Arts & Culture scene, shopping highlights across the county, or interviews with local artists, our bloggers are here to point you in the right direction. Every now and again, we come across a great story about our great county and post it under the Spotlight section of Explorer Annapolis to share with our readers. This curated content allows us to bring you a wider range of all the great things Annapolis & Anne Arundel County has to offer. If you’d like to be a guest blogger, or if you’d like us to share one of your blogs on Explorer Annapolis, email us at adahlgard@symmetry.agency.

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