Do Not Miss

Plan ahead for Annapolis-area holiday events, performances, markets and family outings from December 2–15, 2026.

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 …

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 …

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 …

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 …

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 …

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! …

Week of 10/8-14 Thursday, October 8 Annapolis Powerboat Show | Annapolis City Dock (Oct. 8-11) A Toast to History | Historic London Town & Gardens  A commemoration of the 250th …

Wednesday, November 4 Gaelic Storm | Rams Head on Stage (Nov. 4-5) Friday, November 6 Game Night | iCode Gambrills Annapolis Jazz & Roots Festival | Annapolis: Various Locations (Nov. …

Week of 10/1-5 Thursday, October 1 Hamlet | Classic Theatre of Maryland (Oct. 1-18) Friday, October 2 Annapolis Area Christian School Presents the Annapolis Lower School Parent Preview Day | …