Save the Date: December 2–15, 2026
Plan ahead for Annapolis-area holiday events, performances, markets and family outings from December 2–15, 2026.
Do Not Miss List
Thursday, October 29 Live Arts Maryland Golf Classic | Bay Hills Golf Club A golf fundraiser supporting Live Arts Maryland. Check-in at 8 a.m.; play begins at 9 a.m. Halloween …
Mahjong Mania: Where to Play and Learn Around Annapolis
For hundreds of years, people have gathered to trade and match beautifully painted tiles to pass the time and enjoy one another’s company. The game of mahjong began in China …
Save The Date List
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 …
Do Not Miss List
Week of 10/22-28 Thursday, October 22 Spilling Pictures Presents The Live Spill | 49 West Coffeehouse, Winebar & Gallery Music and stories with the Sweet Leda Duo, Veronique, and Josh …
Porchfest Annapolis Returns Oct. 24 With Free Live Music in Murray Hill
Get ready for an afternoon of live music, neighborhood charm, and community fun! Porchfest Annapolis is back for its second year, bringing local musicians and music lovers together on Saturday, …
Save The Date List
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 …
Fall Theater, Comedy and Live Performances in Annapolis and Beyond
Looking for something different to do this fall? From Broadway musicals and classic plays to stand-up comedy and live music, there are plenty of performances worth adding to your calendar. …
Do Not Miss List
Week of 10/15-21 Thursday, October 15 Great Annapolis Pumpkins | Downtown Annapolis (Oct. 15-30) Middle School Visit Day | Annapolis Area Christian School Annapolis Sailboat Show | Annapolis City Dock …
Save The Date List
Friday, November 13 Annapolis Area Christian School Presents the Annapolis Lower School Parent Preview Day | Annapolis Lower School Live Arts Maryland Presents Pops Concert 1: Rodgers & Hammerstein’s Oklahoma! …