Wednesday, November 25
Santa Photos | Annapolis Mall (Nov. 25-Dec. 24)
Friday, November 27
Jim Patton and Sherry Brokus | 49 West Coffeehouse, Winebar & Gallery
Live folk-Americana music.
Holiday Inn | Classic Theatre of Maryland (Nov. 27-Dec. 27)
Jim Hardy leaves the city and opens a charming country inn.
Saturday, November 28
Small Business Saturday | Downtown Annapolis
Nicole Atkins | Rams Head on Stage
A concert of a bunch of music genres combined, including rock and soul.
Monday, November 30
Healthcare in Retirement | CovingtonAlsina: Virtual
Wednesday, December 2
The Best Christmas Pageant Ever | The Colonial Players (Dec. 2-13)
A crashed church Christmas pageant turns into a heartwarming retelling of the Nativity.
Thursday, December 3
Pet Photos with Santa | Homestead Gardens: Severna Park
The Downtown Annapolis Partnership Presents Midnight Madness | Downtown Annapolis (Dec. 3-17)
A Christmas Carol | Classic Theatre of Maryland (Dec. 3-27)
Friday, December 4
Annapolis Holiday Market | 1040 Annapolis Mall Road, Annapolis (Dec. 4-13)
A Charlie Brown Christmas with the Eric Byrd Trio | Maryland Hall (Dec. 4-5)
Jon McLaughlin | Rams Head on Stage
An evening of music, stories, and holiday cheer.
Saturday, December 5
Historic Annapolis Presents 1776: Yuletide in Revolutionary Annapolis | Hogshead Trades Museum and William Paca House & Garden
Sunday, December 6
Inner West Street Association Presents the Annapolis Chocolate Binge Festival | 60 West Street, Annapolis
Annapolis Moms Deal Drop | Oct. 22, 2026