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 …
Mardi Gras @ Federal House
Come celebrate Mardi Gras with us at Federal House on February 17, 2026 from 11:00 am to 12:00 am!
Veterans Day Special @ Rams Head Tavern
Join us on November 11, 2025 for Veterans Day! As a hearty thank you, all veterans will receive a free bowl of chili courtesy of Rams Head. *Proof of military …
The Nutcracker at Zachary’s Jewelers
Join Zachary’s Jewelers for one of Annapolis’ most magical holiday traditions! On Sunday, November 30, 2025, from 4:00 to 5:30 PM, Zachary’s Jewelers welcomes families for a live performance of …
10th Annual Brigade Holiday Market
Join us in the gorgeous Dahlgren Hall at the US Naval Academy for the event of the season! Get all of your holiday shopping done with hot cocoa while supporting …
New Year’s Eve @ Federal House
Celebrate the New Year with us and join us on New Year’s Eve at Federal House on December 31, 2025 from 11:00 am to 12:00 am!