Looking for the best holiday events in Annapolis and Anne Arundel County? We have the perfect holiday experiences and festive activities as our destination is consistently ranked as a top-Christmas town year over year, remaining a magical place for creating holiday memories with family and friends. For the most up-to-date information, please visit each event’s main website.
Lights on the Bay
November 23, 2025 - January 1, 2026
Enjoy a stunning two-mile drive featuring over 70 animated light displays at Sandy Point State Park.
Jolly Express Cruise
November 22, 2025 – January 1, 2026
An Annapolis favorite during the holidays is a 45-minute “sleigh ride” on Watermark’s Miss Anne along Spa Creek, complete with hot cocoa and holiday tunes.
North Pole Lights Walk
November 28, 2025 – December 28, 2025
Take a self-guided walk through the magical, twinkling and festive gardens of Willow Oak Flower + Herb Farm, where children can meet Santa Claus in his cabin.
Small Business Saturday
November 29, 2025
Support local this holiday season and shop at small businesses in Anne Arundel County to discover unique gifts that your friends and family will love.
Grand Illumination
November 30, 2025
Start your festive holiday season with the annual tree lighting, taking place near Market House and City Dock.
Ballet Theatre of Maryland presents "The Nutcracker"
November 23, 2025, December 13-21, 2025
This familiar story of loved characters like Clara and Uncle Drosselmeier takes on a charming historic Annapolis moment.
Small Business Saturday
November 29, 2025
Support local this holiday season and shop at small businesses in Anne Arundel County to discover unique gifts that your friends and family will love.
Midnight Madness
December 4, 11, 18, 2025
Shop 'til you drop during Midnight Madness! Downtown Annapolis stores will be open until midnight, offering exclusive discounts, festive treats, and a chance to soak in all the holiday displays. It's one of the most anticipated events of the year!
Annapolis Chocolate Binge Festival
December 7, 2025
Mhmm, chocolate! On the first block of West Street in downtown Annapolis, indulge in chocolate desserts and warm beverages. Family-friendly activities and holiday arts and crafts available for purchase make this a true festival to savor.
Eastport Yacht Club Lights Parade
December 13, 2025
Another local favorite during the holidays is experiencing the magic of the nautical and Annapolitan themed lights through Annapolis Harbor.
Annapolis Holiday Market
December 13, 18, 19, 20, 21, 2025
The Annapolis Holiday Market is back for year four! Explore 100+ artisans, tasty treats, and festive fun—now on the front lawn of St. John’s College.
Military Bowl Game
December 27, 2025
Enjoy a lively bowl game at Navy-Marine Corps Memorial Stadium featuring two National Capital region’s college football teams. The game will match teams from the ACC and the American Athletic Conference.
New Year’s Eve Celebrations
December 31, 2025
Ring in 2026 with friends and family under an incredible firework show at City Dock.
