Presidents’ Day at the Museum of Historic Annapolis
Celebrate Presidents’ Day at the Museum of Historic Annapolis! Drop in and join us for a day of fun and discovery as we honor America’s presidents through hands-on activities and …
Ugly Sweater Party
Mark your calendars for this Ugly Sweater Party on December 19, 2025 at Club Federal! There will be a giveaway and drink specials all night!
SoCo Holiday Market
Calling all fellow procrastinators! Come join us for our 5th annual last minute Holiday Market! If you are a gift getting procrastinator like me, this market is perfect for you! …
Gents’ Last Call: Sliders & Spirits at Zachary’s Jewelers
Finish your holiday shopping in style at Zachary’s Jewelers’ annual Gents’ Last Call event, an Annapolis tradition for last-minute shoppers. From December 22-23 (10 AM-8 PM) and December 24 (10 …
Single During the Holidays
Who says the holidays are just for couples? Being single during the holiday season opens up endless opportunities to make the celebrations completely your own. From spontaneous solo adventures to …
Holiday Walking Tour
Explore the decorated streets of Annapolis and learn of holiday traditions from the past with your period-attired guide.
Cheers to the Season: Annapolis’ Best Holiday Drinks
Whether you’re strolling downtown for Midnight Madness, shopping at the Annapolis Town Center, or simply leaning into the festive mood, Annapolis’ restaurants and bars go all-in for the holidays. If …
Zachary’s Jewelers Midnight Madness Night Two
Join Zachary’s Jewelers for Night Two of Midnight Madness on Thursday, December 11, featuring complimentary pours and festive treats, a special guest experience at the Breitling Bar, a gift with …
Brigade Holiday Market
Join us in Dahlgren Hall at the US Naval Academy for the holiday event of the season! Shop local at the Brigade Holiday Market. Complimentary cookies, hot chocolate, and hot …
Zachary’s Jewelers Midnight Madness One
Join Zachary’s Jewelers for night one of Midnight Madness on Thursday, December 4, featuring complimentary pours and festive treats, a special guest experience at the Breitling Bar, a gift with …