Wednesday, November 18
Deer Tick | Rams Head on Stage
Thursday, November 19
Middle School Visit Day | Annapolis Area Christian School
Friday, November 20
Compass Rose Theater Presents It’s a Wonderful Life: Radio Show | Live Arts Studio (Nov. 20-Dec. 5)
A radio play adaptation about George Bailey and his reflection on his life on Christmas Eve.
Saturday, November 21
Magical Polar Express Dance Camp | Davy Dance Academy
Santa’s in Town | Uncharted Annapolis
Free photos with Santa.
Navy Football vs Memphis | Navy-Marine Corps Memorial Stadium
Historic Annapolis Presents Chime After Chime: How a Clock Knows the Time | Hogshead Trades Museum
Grand Illumination | Homestead Gardens: Davidsonville
Over 250,000 lights decorating Homestead Gardens.
Sunday, November 22
Ballet Theatre of Maryland Presents The Nutcracker | Coppermine Pantherplex
Inner West Street Association Presents the Great Annapolis Gingerbread Houses | Annapolis Visitors Center (Nov. 22-Dec. 20)
Monday, November 23
SPCA of Anne Arundel County Presents Lights on the Bay | Sandy Point State Park (Nov. 23-Jan. 3)
Friday, November 27
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
Monday, November 30
Healthcare in Retirement | CovingtonAlsina: Virtual
Tuesday, December 1
The Holidays with Canadian Brass | Maryland Hall
The War And Treaty | Rams Head on Stage
Soulful country duo.
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.
The Real Mom Recap | Oct. 19, 2026