6 Holiday Events in Annapolis, MD

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Ranked one of America’s best towns for the holidays by Travel and Leisure, Annapolis, MD, has it all this holiday season from late night shopping to extravagant light displays, and many more. This city will provide you with plenty of ways to get into the holiday spirit with daily activities to keep the whole family entertained. If you enjoy everything about the holidays from Christmas light displays to parades, you’ll definitely want to be in Annapolis this holiday season!

Shopping Center in Annapolis, MD

Are you looking for a place to get all of your holiday shopping done? If so, look no further than Annapolis Harbor Center! Our shopping center carries a wide variety of stores from Old Navy to GameStop. Here, you’ll find something for everyone in the family. Take advantage of our delicious dining options or maybe, catch a movie on the big screen at Bow Tie Cinemas, located right in the mall. Be sure to visit us this holiday season while you’re on the hunt for the perfect gifts.

Chocolate Binge Festival

Nothing screams “Happy Holidays!” like sweets and candy galore. Ring in this holiday season and surround yourself with more chocolate than you can imagine! More than two dozen vendors will hit the streets of Downtown Annapolis with truffles, fudge, cookies, cakes, and plenty more! Complete with a live music, a moon bounce, snowball race, and a marketplace, the festival will be great fun for chocolate lovers of all ages! The festival will take place Dec. 3 from 12 p.m. – 5 p.m. on West Street.

Lights on the Bay

From Nov. 18 – Jan. 1, Sandy Point State Park will be illuminated by all kinds of new and classic light displays along the Chesapeake. The light show has become a tradition in Annapolis as this year marks its 24th anniversary. You can watch the light show from the warmth and comfort of your car as you take a drive along the shore of the Chesapeake Bay. Take in over 60 animated and still displays while spreading holiday cheer and joy. If your children want a more interactive experience, they can participate in a scavenger hunt, picking out specific items from the displays.

Holiday Candlelight Stroll

Take a stroll through Christmas past this winter as Annapolis transforms into an educational trip down memory lane. Learn all about the history behind evergreens, yule logs, Christmas trees, and even Santa Claus as a tour guide takes you on a one and a half hour walking tour of the state’s capital. Surrounded by glowing lanterns and holiday décor, you will learn what Christmas is all about while enjoying a festive walk through town. Included in the Holiday Candlelight Stroll is an interior tour of an 18th century art museum, the Hammond-Harwood House.

2017 Military Bowl

Football and the holidays go together like winter and snow. There’s nothing better than coming together with your family and friends to watch a game of football, so why not take everyone down to the Navy-Marine Corps Memorial Stadium for the annual Military Bowl? Take some time this holiday season to watch a football game and support a great cause. On Dec. 28, representatives from the Atlantic Coast Conference and American Athletic Conference will go head-to-head at the tenth annual Military Bowl. All proceeds will benefit the United Service Organization (USO), an organization that supports deployed troops, military families, and wounded members of the armed forces.

Eastport Yacht Club Lights Parade

Every year, Annapolis Harbor is illuminated by a variety of colorful lights at the Eastport Yacht Club Lights Parade. It’s a chance for boat owners to showcase their ride as well as their holiday spirit as members of the community watch the parade across the waterfront. You may just be used to seeing extravagantly decorated houses and storefronts around the holidays. Shake things up this season by taking in the sight of brightly illuminated boats as they parade on the water, creating a view like no other.

Midnight Madness Holiday Shopping

If you’re a night owl who wants to beat the last minute crowd of frantic shoppers in search of the perfect gift, be sure not to miss Midnight Madness. On select Thursday nights in December, stores in downtown Annapolis will leave their doors open a little later than usual while the streets are filled with live music, food, and holiday cheer. Midnight Madness is a great opportunity to get all of your shopping out of the way during the busy holiday season, leaving you with more time to relax and spend with your loved ones. Mark your calendar for Dec. 7, 14, and 21 for Downtown Annapolis’ Midnight Madness!

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