If you're in need of a little holiday spirit in a magical place, look no further than right here in Annapolis. Throughout the centuries in American History, people have flocked to our charming city to celebrate family, friends, and the holiday season.

Annapolis seems to fill with a certain air of magic during the holiday season. Lights and wreaths are hung on the countless 18th-century homes;locals and visitors wander in and out of small shops across the city; and carolers patrol the brick-laden streets of downtown – all while the harbor gently rocks wintering boats throughout the chilly months. Adding to its charm is the fact that this scene has been playing out, more or less, for over 300 years! 

With a few centuries of history, a magical ambiance permeating the city, holiday cheer echoing through the brick streets, it’s easy to see why Annapolis is consistently named one of America’s Best Towns for the Holidays by Travel+Leisure. (Not to mention that it's also as one of the Most Beautiful Towns in America by Condé Nast Traveler).

Get in the Holiday Spirit

If the magic of Annapolis’ old world-charm and decorations aren’t enough for you, there are a ton of events happening throughout the holidays to ensure you’re making the most out of the season. It all kicks off with the return of Lights on the Bay – Annapolis’ drive through light display at Sandy Point State Park – and ends with a celebratory firework display over the harbor to bring in the New Year. Between the two are a wide range of events sure to make any scrooge excited for the holiday season. 

Lights on the Bay
Nov 24th – Jan 1st (5:00 pm to 10:00 pm)

The SPCA of Anne Arundel County presents the Lights on the Bay holiday light show (held at Sandy Point State Park), featuring a two-mile scenic drive along the Chesapeake Bay with about 70 animated and stationary displays illuminating the roadway. In addition to popular classic displays such as a colonial village inspired by historic Annapolis and one of the USNA midshipmen tossing their hats in the air, guests will also be treated to the North Pole Village & Enchanted Fairy Tales. Perfect for a night out with the whole family!

Grand Illumination - City Tree Lighting
Dec 1st (5:30 pm to 7:00 pm)

With support from the Annapolis business community, the Annapolis Jaycees (Junior Chamber of Commerce) will once again host the Lighting of the Tree in Annapolis during the city’s Grand Illumination event at the City Dock. Watch Santa arrive in town and enjoy singing and dance performances by area youth. The Jaycees will provide refreshments and ornaments children can use to decorate the tree. Attendees are invited to bring nonperishable food items and new, unwrapped toys for the Jaycees’ annual Angel Tree Project. You don't want to miss this one: Condé Nast Traveler has named it The Best Christmas Tree in Maryland!

Fire & Ice Festival
Dec 7th (4:00 pm to 8:00 pm)

Take some time away from the busy holiday season for the Annapolis Towne Centre’s Fire & Ice Festival on December 7, 2019, from 4-8 pm. Embrace the winter with smores over a cozy fire, live music, a light show, on-site vendors, cocktails, shopping, and tasty bites. Visit Annapolis Towne Centre online for more information.

Chocolate Binge Festival
Dec 8th (12:00 pm to 5:00 pm)

Are you a chocoholic in need of a fix? You won’t want to miss the 5th Annual Chocolate Binge Festival. Two dozen local chocolate vendors will be selling chocolate specialties, including chocolate caramels, cakes, bars, truffles, fudge, cookies, candies, hot chocolate, much and more. Enjoy live music, roasting S'mores with the Anapolis Fire Department, a gingerbread house moon bounce, Cocoa with the PoPo, a holiday market, the lighting of the Holiday Light Canopy and, of course, with a visit from Santa.

Midnight Madness
Dec 5th, 12th (6:00 pm to Midnight), and 19th (6:00 pm to 11:00 pm)

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. Enjoy food, music, shopping deals, and much more.  The festivities and shopping take place along Maryland Avenue and State Circle, West Street, Main Street, Market Space, Randall Street and Dock Street. 

Illuminated London Town
Fridays and Saturdays in December (6:00 pm to 9:00 pm)

Experience the magic of a winter evening at Illuminated London Town! Sip hot cider and roast s'mores beside roaring fires in the Historic Area of London Town and Gardens. Explore the gardens illuminated with festive holiday lights. Discover colonial nighttime festivities and holidays at candlelit William Brown House, decorated for the season. Enjoy special performances in the gardens each week. 

Eastport Yacht Club Lights Parade 
Dec 14 (6:00 pm to 8:00 pm)

The holiday light parade bursts upon the Annapolis waterfront with up to 40 boats of all shapes and sizes, power and sail, brightly decorated with thousands of lights and crewed by jolly shipmates. This festive maritime event is great fun for the entire family. Skippers participate for the fun of it, and circle the waterfront in two fleets: one circling in front of Eastport, the City Dock and the Naval Academy seawall, the other circling the length of Spa Creek, inside the bridge.  

The Easport Yacht Club Lights Parade is sponsored by Long & Foster Real Estate - Eastport Branch. Full list of sponsors here.

Military Bowl® presented by Northrop Grumman
Dec 27th (12:00 pm kick-off)

Get ready for one of the best days of the year in Annapolis! Starting with the Military Bowl Parade (featuring the beloved Budweiser Clydesdales) in downtown Annapolis, the 2018 Military Bowl will pin the ACC against the ACC for season bragging rights. For the eighth consecutive bowl season, the Military Bowl will be benefiting the USO and will provide at least $100,000 to the USO. Complimentary tickets to troops and their families will also be distributed for the game through the USO of Metropolitan Washington-Baltimore in early December. Tailgate before the game, or head to one of the many bars in town. However, be sure to pace yourself, because the day is just getting started!

New Year’s Eve Celebration
Dec 31 (3:00 pm to 12:00 am)

Right after the Military Bowl, head to downtown Annapolis to celebrate the new year with a massive fireworks display. Family activities fill the day and music and dancing fills the night at this annual celebration welcoming the New Year. Kids’ activities will take place with activities that include face painting, an obstacle course, moon bounces and live music. The festivities wrap up with on-site fireworks for the kids, then, it’s off to area restaurants for dinner with the kids. The second round of festivities includes live music and dancing at Susan Campbell Park at City Dock beginning at 8:00 p.m. and ending with midnight fireworks.

Stay for More

With shopping options ranging from small boutiques to outlet malls, Annapolis and Anne Arundel County is the perfect place to get your early (or last minute) shopping taken care of. Or, if you’re looking to stay for a while, the ExperienceBWI area, as well as the hotels and B&Bs in and around Annapolis, are a wonderful way to take some time for yourself while enjoying the season. With a ton of dining and entertainment options to choose from as well, staying in the area this holiday season may just be the best gift you give this year!

Featured Holiday Hotel Packages:

Whether you're looking to get away for a weekend or to spend a week with us, there's plenty to see, do, taste, and experience in Annapolis this winter. Book your stay between November 25th, 2019 and February 29th, 2020 to take advantage of the hotel deals HERE and make the most out of your winter visit to Annapolis!