Annual Champagne Tasting
It’s the most wonderful time of year which means it’s time for our Annual Champagne Tasting! Join us on Saturday, December 20, 2025 between 4:00 pm – 7:00 pm to …
Jeff’s Christmas Light Show Spectacular
Don’t miss Jeff’s Christmas Light Show Spectacular! Show starts at 7:00 pm, runs for 15 minutes, and repeats until 9:00 pm. The market and walk-through display open at the end …
Holiday Celebration @ Paws at the Mall
Join us at Paws at the Mall on December 13, 2025 for a celebration packed with joy, goodies, and giving! We will be having an afternoon filled with festive furry …
Candlelight: Christmas Carols on Strings
Candlelight concerts bring the magic of a live, multi-sensory musical experience to awe-inspiring locations like never seen before in Annapolis. Get your tickets now to discover the music of Christmas Carols …
Pictures with Santa @ Blue Crab Cupcakes
Santa Todd will be visiting Blue Crab Cupcakes! As a thank-you for his time, we’ll be making a donation to his charity, Gold in Fight, supporting the fight against childhood …
A Merry Mix-Up
Don’t miss A Merry Mix-Up! Celebrate the season with Santa, Frosty, and more at the Talent Machine’s annual holiday spectacular, a family tradition for 38 years. Get your tickets here! …
Chanukah Bowl
Don’t miss this Chanukah Bowl! Tickets are $15-$20 and includes the game, shoes, and a special Chanukah program. Chanukah Bowl will take place at Annapolis Bowl. Register here!
The Eric Scott Trio Annual Holiday Concert
Honesty, soul, and the celebration of life’s joy and pain. These are the things that consistently define Eric’s music and performance. As an artist, he’s powerful, sensual, and kind, with …
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 …