East of Maui Santa Paddle
Join East Santa for a holiday paddle around Annapolis Harbor, City Dock, and Spa Creek. There will be a brief safety meeting at 10:00 am, pictures with Santa, and launching …
Annapolis Holiday Market
The Annapolis Holiday Market will feature 100 artisan vendors, specialty food stalls, and festive entertainment. Visitors can shop for handcrafted gifts, including jewelry, pottery, glass art, and home décor, while …
Operation Elf Adventure: Fence & Deck Connections 19th Annual Holiday Drive
Step into the magic of the season at Fence & Deck Connection’s 19th Annual Holiday Drive! This year’s Operation Elf Adventure transforms kids into official North Pole elves as they …
Songs of the Season
Join the Naptown Philharmonic Chorus, directed by Jeanne Kelly, for its inaugural concert, Songs of the Season, celebrating this happy time of year. The repertoire includes these favorites, and yes, …
Ring the Salvation Army Bell
Silver bells, silver bells: it’s Christmastime in the city! Join the Salvation Army as a volunteer bell-ringer at one of our iconic Red Kettles throughout Annapolis and Anne Arundel County. …
Heroes Holiday Market
Don’t miss the Heroes Holiday Market! It will take place on December 14, 2025 from 8:00 am to 11:00 am at Heroes Pub. There will be different vendors, custom cocktails, …
North Pole Lights Walk
Take a self guided walk to the North Pole! Let the North Pole Fairy send you on your way through the garden flowers and arctic animals to the North Pole …
Christmas Concert w/ Ryan McKasson & Hanneke Cassel
Don’t miss the 35th Annual Winter Solstice/Christmas Concert with Ryan McKasson and Hanneke Cassel! It will take place on December 14, 2025 at 3:00 pm and 7:00 pm at St. …
Cypress Creek Assisted Living Community Holiday Gift Drive
Join us at the Cypress Creek Assisted Living Holiday Gift Drive to spread some cheer and make a difference in the community! How You Can Help: Donate new packaged items …
Tiny Art Show + Artisan Market
Discover the joy of small-scale creativity at our Tiny Art Show + Artisan Market. This festive showcase features 14 local artists presenting original wall art—perfect for gift giving, collecting, or …