Annapolis During the Holidays

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The first places we might associate with the holidays are New York City and its famous Rockets and the Rockefeller Square Christmas tree, but don’t count Annapolis out! Thanksgiving is just as cozy and Christmas shines just as bright in and around the beautiful and historic coastal town of Annapolis, Maryland during the holidays.

Don’t be late because the fun starts in early November! You could start with “Pictures with Santa” on November 5th when Eastport Fire Company on Bay Ridge Avenue in Annapolis takes family photos (which can include your family pet!) in front of a fire engine. Or dine, enjoy live music and shop for the holidays at West and Calvert streets that very same day during the Annapolis Holiday Market First Sunday Arts Festival.

Maybe you want to try something different? How about the Gregorian Pure Chants Tour at Maryland Hall November 13th? This innovative live performance fuses the haunting sounds of Gregorian chants with the rock songs of musicians including Lenny Kravitz, Peter Gabriel, Queen and more!

More of a traditionalist? Then take in a show November 24, 25 or 26th at the Classic Theatre of Maryland where a heartwarming musical adaptation of Irving Berlin’s beloved White Christmas will be performed.

Want to give back to the less fortunate while you have fun? Try the Gobble Til You Wobble Facebook 1-mile, 5K or 10K virtual run on November 23rd, which will donate 15% of your registration fee to Feeding America – our nation’s largest domestic hunger relief organization.

December, when you can enjoy holiday boat tours along the Chesapeake, candlelit evening Christmas historic tours, amazing Christmas light displays and Christmas parades by land and sea, is just as festive and lovely!


Gary Wells

Owner of Window Expressions, Annapolis' premier custom window treatment specialist. With years of of experience in the industry, Gary takes pride in his keen eye for design and his ability to transform clients' visions into reality. He finds joy in leading a local, family-owned business committed to putting the "custom" in customer service.

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