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 …
Reading of “A Christmas Carol”
Please join SERC for the third annual reading of “A Christmas Carol.” It will take place in the atmospheric front parlor of the decorated historic Woodlawn house. The reading is …
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, …
Parade of Light
Join us for a spin at the annual Menorah Car Parade here in Annapolis. An experience you won’t want to miss! The parade will be leaving Safeway (2635 Housley Road, …
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. …