Wednesday, December 2
The Best Christmas Pageant Ever | The Colonial Players (Dec. 2–6 & 9–13)
The Herdman children turn a church Christmas pageant upside down in this family holiday play.
SPCA Lights on the Bay | Sandy Point State Park (Dec. 2–15; runs Nov. 23–Jan. 3)
Drive through holiday light displays while supporting the SPCA of Anne Arundel County.
It’s a Wonderful Life: A Live Radio Play | Live Arts Studio, Annapolis Mall (Runs Nov. 20–Dec. 5)
Compass Rose Theater brings George Bailey’s Christmas Eve story to the stage as a radio play. See the organizer’s performance schedule.
Thursday, December 3
Midnight Madness | Downtown Annapolis (Dec. 3 & 10)
Shop local, enjoy festive entertainment and explore downtown’s decorated streets. Begins at 4 p.m.
Friday, December 4
Annapolis Holiday Market | Annapolis Mall (Dec. 4–6 & 11–13)
Browse an outdoor artisan holiday market with free admission and parking.
A Charlie Brown Christmas with the Eric Byrd Trio | Maryland Hall (Dec. 4–5)
Hear the jazz trio’s interpretation of the holiday classic, with performances at 6 and 8 p.m. both days.
Christmas Traditions by Candlelight | William Paca House (Dec. 4, 11 & 12)
Take a guided holiday tour exploring seasonal traditions, with tours at 11 a.m. and 4 p.m.
Saturday, December 5
1776: Yuletide in Revolutionary Annapolis | William Paca House & Hogshead Trades Museum (Dec. 5)
Explore holiday traditions through living history, seasonal music and family activities, from 2–5:30 p.m.
Santa’s in Town | Uncharted Annapolis (Dec. 5 & 12)
Visit for free photos with Santa. December 12 runs 10 a.m.–noon; check with the store for December 5’s time.
Holiday Inn | Classic Theatre of Maryland (Dec. 5–6, 9 & 11–13)
Irving Berlin’s musical follows Jim Hardy as he opens a country inn that celebrates the holidays with entertainment.
Sunday, December 6
Annapolis Chocolate Binge Festival | West Street, Annapolis (Dec. 6)
Enjoy chocolate vendors, holiday shopping and family entertainment from 11 a.m.–4 p.m. Admission and tasting tickets are separate.
Wednesday, December 9
The Nutcracker: Mini Performances | Maryland Hall (Dec. 9)
Ballet Theatre of Maryland’s condensed student and senior matinees begin at 9:30 and 11:30 a.m.
Mickey Guyton & Friends Holiday Tour with Special Guest Denitia | Rams Head on Stage (Dec. 9)
Country singer Mickey Guyton brings her holiday tour to Annapolis. Show at 8 p.m.; doors at 7 p.m. All ages.
Thursday, December 10
Midnight Madness on West: Annapolis Holiday Market | West Street & Church Circle (Dec. 10)
Browse art vendors and enjoy live entertainment at this outdoor holiday market, from 6–10 p.m.
Friday, December 11
Cookies & Cocoa with Santa | Severna Park Community Center (Dec. 11)
This free indoor family event includes Santa photos, holiday crafts and seasonal treats, from 5:30–7:30 p.m.
Carbon Leaf | Rams Head on Stage (Dec. 11–13)
Four shows: Friday at 8:30 p.m.; Saturday at 3:30 and 8:30 p.m.; Sunday at 1 p.m.
Saturday, December 12
Ballet Theatre of Maryland: The Nutcracker | Maryland Hall (Dec. 12–13; also Dec. 19–20)
An Annapolis-inspired take on Clara’s holiday adventure, with Saturday shows at 1 and 7 p.m. and Sunday shows at 1 and 4:30 p.m.
Eastport Yacht Club Lights Parade | Annapolis Harbor (Dec. 12)
Watch illuminated boats parade through the harbor beginning at 6 p.m.
Sunday, December 13
Voices of the Season | Eastport United Methodist Church, Annapolis (Dec. 13)
The Naptown Philharmonic Orchestra Chorus presents new and traditional holiday music, from 7–8:30 p.m.
Monday, December 14
December Cabaret | Classic Theatre of Maryland (Dec. 14–15)
Evening cabaret performances begin at 7:30 p.m. both nights.
Tuesday, December 15
Top IRA Planning Mistakes to Avoid | Online (Dec. 15)
CovingtonAlsina’s virtual presentation covers common IRA planning mistakes, from 6–7 p.m. Registration is required.
The Real Mom Recap | Nov. 2, 2026