Events are subject to cancellation without notice. To avoid any inconvenience, call ahead to confirm dates, times and availability.

Voted one of the best towns for the holidays by Travel & Leisure, Annapolis is a must-see in December. The downtown streets of Annapolis are all gussied up with garland and lights, and just a stroll around town is enough to get you into the holiday spirit. At the 4th Annual Chocolate Binge Festival on December 2nd, sample all sorts of chocolate-and enjoy live entertainment-as you stroll the streets. But there's more. The Eastport Yacht Club Lights Parade, on the second Saturday of December at 6:00 p.m., draws a merry crowd to watch as dozens of beautifully decorated boats light up the Annapolis Harbor. Midnight Madness, on three consecutive Thursday evenings in December, brings out shoppers and revelers as the stores in downtown Annapolis stay open until Midnight or 11:00 p.m.. The excitement doesn't die down after Christmas. Football fans descend on the Navy-Marine Corps Memorial Stadium for an exciting college bowl game, the Military Bowl presented by Northrop Grumman on December 31 at 12:00 p.m. To cap off the year, the city of Annapolis also holds a fun, family-friendly New Year's Eve Celebration beginning at 3:00 p.m. on December 31st at City Dock and concluding with festive fireworks. 

Midnight Madness Holiday Shopping
Where: Downtown Annapolis
Admission: Free

State House by Candlelight
When: TBD
Where: Maryland State House
Admission: Free

Enjoy this annual open house featuring performance by young musicians and vocalists from throughout Maryland. The oldest State House in continuous legislative use in the nation will be adorned with 24 christmas trees representing every Maryland county and Baltimore City. Photo identification is required for individuals age 16 and older.

Illuminated London Town
Where: Historic London Town & Gardens

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. 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. 

Lights on the Bay 
Where: Sandy Point State Park, 1100 East College Parkway, Annapolis
Admission: $15, car; $50, bus

Don't miss this spectacular drive-through holiday lights show beside the Chesapeake Bay. The event features more than 60 animated and stationary displays, including traditional Maryland-themed favorites, holiday and children’s displays. Proceeds benefit the SPCA of Anne Arundel County. Visit "Lights on the Bay" for more information.

Holiday Open House & Greens Sale

Join the Hammond-Harwood House Museum for a special Holiday season where art, design, and the beautiful state of Maryland come together. Local garden clubs create an inspirational floral design with faux and dried pieces inspired by the period room’s architecture and collections. Decorating has been a yearly tradition since 1953 and we invite you to enjoy Annapolis’ architectural jewel during this festive season. To purchase tickets click here.

Holiday Candlelight Stroll

Learn about the origin of holiday traditions – including the significance of evergreens, Yule logs, Christmas trees and Santa Claus as you stroll through Annapolis with a festively attired guide. Includes a tour of the Hammond-Harwood House. Visit for more information.

From Novice to Knowledgeable: Unwrapping Chocolate's Secrets

Participants will get hands-on when they grind cacao nibs into chocolate the way it would have been done in the 18th century. Different types of cacao and the history of chocolate processing from the pre-industrial days to the modern-day will also be explored, and, at each step in the process, different types of chocolates will be sampled to make this scrumptious chocolate journey complete. To purchase tickets click here.

Jolly Express Cruise

Enjoy a 45-minute, holiday-inspired, “sleigh ride” cruise aboard the reindeer-bedecked Miss Anne. Cruise includes holiday music, hot cocoa, and Captain Santa at the helm. Visit for more information.

38th Annual Eastport Yacht Club Lights Parade

Brightly decorated boats parade around the Annapolis waterfront in one of the City’s signature events. Thousands of lights and a host of jolly revelers make this a fun holiday event for the entire family. Prime viewing areas include:  Eastport, Spa Creek, City Dock and Naval Academy sea wall. Sponsored by the Eastport Yacht Club. Visit the Eastport Lights Parade or Facebook for more information.

Lights Parade Dinner & Dessert Cruise

An Annapolis tradition. Enjoy dinner at Severn Inn followed by a dessert cruise aboard the luxurious Catherine Marie to watch the decorated boats cruising along Spa Creek in the Eastport Yacht Club Lights Parade. Visit their site for more information here.

2020 Military Bowl
When: TBA
Where: Navy-Marine Corps Memorial Stadium (550 Taylor Avenue, Annapolis)
Tickets: 888-841-2787

The Military Bowl® presented by Northrop Grumman, benefiting the USO, will match a team from the Atlantic Coast Conference (ACC) against an opponent from the American Athletic Conference (AAC). Visit for more information.

City of Annapolis New Year’s Eve Celebration

Family activities fill the day and music and dancing fills the night at this annual celebration welcoming the New Year. For the second year, kids’ activities will take place on Weems Whelan fields behind Maryland Hall and Bates Middle School. Participants are invited to park at Park Place garage and take City of Annapolis-provided shuttles to and from the new location. Activities will include face painting, an obstacle course, moon bounces and music performed by kids’ rock bands. The first round of festivities wraps up with on-site fireworks at approximately 5:30 p.m. 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. 

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New Year’s Eve Fireworks Cruise in Annapolis

Ring in the New Year on an exclusive and FUN fireworks cruise on Catherine Marie in Annapolis, Watermark's flagship vessel. Includes and excellent - and comfortable - view of the city of Annapolis' New Year's Eve fireworks from the sparkling water. Enjoy dancing, DJ entertainment, celebrating and a full cash bar on board! Light snacks will be served. There will be hats and party noise makers, light bites and mini desserts, a great DJ with a festive countdown and a complimentary champagne toast at midnight! For adults 21 & over only. For more information, check out

Additional December Links

  • Military Bowl

    Military Bowl

    Get tickets and information on this year's Military Bowl presented by Northrop Grumman.

    Learn more