Annapolis Events December 2026

Concerts, sports, comedy shows, Broadway performances, and live events across Annapolis, MD.

Updated: November 13, 2026

Explore upcoming events in Annapolis in December 2026, including concerts, sports events, comedy shows, Broadway performances, festivals, and live entertainment across the city and nearby areas. Browse events by date, venue, category, and neighborhood throughout the month.

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48 Upcoming Events
7 Event Categories

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Popular Events in December

Explore top concerts, sports events, comedy shows, and live performances happening this month.

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Browse events happening each day during December 2026.

Annapolis Events Schedule – December 2026

Browse concerts, sports, comedy shows, Broadway performances, festivals, and live events across Annapolis.

Upcoming Confirmed Events 48

Dec 03, 2026, 7:30 PM Thu — MUSICAL / PLAY: A Christmas Carol at Main Stage At Classic Theatre of Maryland • 125 seats, 1804 West Street, Annapolis, MD 21401, US. From $92, Avg Ticket Price: ~ $129, Tickets Available: 34. Select Seats

Dec 03, 2026, 8:00 PM Thu — ALTERNATIVE, Pay Later Available: Trevor Hall at Rams Head On Stage • 300 seats, 33 West Street, Annapolis, MD 21401, US. From $298, Avg Ticket Price: ~ $344, 2 tickets remaining! Select Seats

Dec 04, 2026, 8:00 PM Fri — MUSICAL / PLAY: A Christmas Carol at Main Stage At Classic Theatre of Maryland • 125 seats, 1804 West Street, Annapolis, MD 21401, US. From $92, Avg Ticket Price: ~ $127, 28 tickets remaining! Select Seats

Dec 04, 2026, 8:00 PM Fri — JAZZ / BLUES: Jon McLaughlin at Rams Head On Stage • 300 seats, 33 West Street, Annapolis, MD 21401, US. From $65, Avg Ticket Price: ~ $414, 10 tickets remaining! Select Seats

Dec 05, 2026, 2:00 PM Sat — MUSICAL / PLAY, Weekend Event: Irving Berlin's Holiday Inn at Main Stage At Classic Theatre of Maryland • 125 seats, 1804 West Street, Annapolis, MD 21401, US. From $92, Avg Ticket Price: ~ $127, Tickets Available: 37. Select Seats

Dec 05, 2026, 8:00 PM Sat — MUSICAL / PLAY, Weekend Event: A Christmas Carol at Main Stage At Classic Theatre of Maryland • 125 seats, 1804 West Street, Annapolis, MD 21401, US. From $92, Avg Ticket Price: ~ $232, Tickets Available: 52. Select Seats

Dec 06, 2026, 2:00 PM Sun — MUSICAL / PLAY, Weekend Event: Irving Berlin's Holiday Inn at Main Stage At Classic Theatre of Maryland • 125 seats, 1804 West Street, Annapolis, MD 21401, US. From $92, Avg Ticket Price: ~ $125, Tickets Available: 35. Select Seats

Dec 06, 2026, 7:30 PM Sun — MUSICAL / PLAY, Weekend Event: Irving Berlin's Holiday Inn at Main Stage At Classic Theatre of Maryland • 125 seats, 1804 West Street, Annapolis, MD 21401, US. From $92, Avg Ticket Price: ~ $130, Tickets Available: 36. Select Seats

Dec 08, 2026, 8:00 PM Tue — POP / ROCK, Best Value: S. Carey at Rams Head On Stage • 300 seats, 33 West Street, Annapolis, MD 21401, US. From $53, Avg Ticket Price: ~ $68, Tickets Available: 260. Select Seats

Dec 09, 2026, 7:30 PM Wed — MUSICAL / PLAY: Irving Berlin's Holiday Inn at Main Stage At Classic Theatre of Maryland • 125 seats, 1804 West Street, Annapolis, MD 21401, US. From $92, Avg Ticket Price: ~ $125, 28 tickets remaining! Select Seats

Dec 09, 2026, 8:00 PM Wed — COUNTRY / FOLK: Mickey Guyton at Rams Head On Stage • 300 seats, 33 West Street, Annapolis, MD 21401, US. From $65, Avg Ticket Price: ~ $588, 8 tickets remaining! Select Seats

Dec 10, 2026, 7:30 PM Thu — MUSICAL / PLAY: A Christmas Carol at Main Stage At Classic Theatre of Maryland • 125 seats, 1804 West Street, Annapolis, MD 21401, US. From $92, Avg Ticket Price: ~ $128, 26 tickets remaining! Select Seats

Dec 11, 2026, 8:00 PM Fri — MUSICAL / PLAY: Irving Berlin's Holiday Inn at Main Stage At Classic Theatre of Maryland • 125 seats, 1804 West Street, Annapolis, MD 21401, US. From $92, Avg Ticket Price: ~ $130, 27 tickets remaining! Select Seats

Dec 12, 2026, 1:00 PM Sat — BALLET, High Demand, Weekend Event: Ballet Theatre of Maryland: The Nutcracker at Maryland Hall For The Creative Arts, 801 Chase Street, Annapolis, MD 21401, US. From $86, Avg Ticket Price: ~ $150, Tickets Available: 133. Select Seats

Dec 12, 2026, 2:00 PM Sat — MUSICAL / PLAY, Weekend Event: A Christmas Carol at Main Stage At Classic Theatre of Maryland • 125 seats, 1804 West Street, Annapolis, MD 21401, US. From $92, Avg Ticket Price: ~ $276, Tickets Available: 35. Select Seats

Dec 12, 2026, 3:30 PM Sat — POP / ROCK, Best Value, Weekend Event: Carbon Leaf at Rams Head On Stage • 300 seats, 33 West Street, Annapolis, MD 21401, US. From $53, Avg Ticket Price: ~ $252, 12 tickets remaining! Select Seats

Dec 12, 2026, 7:00 PM Sat — BALLET, Weekend Event: Ballet Theatre of Maryland: The Nutcracker at Maryland Hall For The Creative Arts, 801 Chase Street, Annapolis, MD 21401, US. From $76, Avg Ticket Price: ~ $162, Tickets Available: 126. Select Seats

Dec 12, 2026, 8:00 PM Sat — MUSICAL / PLAY, Weekend Event: Irving Berlin's Holiday Inn at Main Stage At Classic Theatre of Maryland • 125 seats, 1804 West Street, Annapolis, MD 21401, US. From $92, Avg Ticket Price: ~ $127, Tickets Available: 32. Select Seats

Dec 13, 2026, 1:00 PM Sun — BALLET, Weekend Event: Ballet Theatre of Maryland: The Nutcracker at Maryland Hall For The Creative Arts, 801 Chase Street, Annapolis, MD 21401, US. From $76, Avg Ticket Price: ~ $147, Tickets Available: 178. Select Seats

Dec 13, 2026, 2:00 PM Sun — MUSICAL / PLAY, Weekend Event: Irving Berlin's Holiday Inn at Main Stage At Classic Theatre of Maryland • 125 seats, 1804 West Street, Annapolis, MD 21401, US. From $92, Avg Ticket Price: ~ $127, Tickets Available: 32. Select Seats

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January

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September

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October

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November

This Month

Events in November 2026

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About Events in Annapolis During December 2026

December 2026 features concerts, sports games, comedy shows, Broadway performances, festivals, and live entertainment across Annapolis and nearby MD areas. Major arenas, theaters, clubs, and entertainment venues continue to update their schedules throughout the month.

Browse All Events in December

Browse concerts, sports events, comedy shows, Broadway performances, festivals, and live entertainment happening this month.

A Christmas Carol

1804 West Street, Annapolis, MD 21401

Event Dates 1843

Dec 03, 2026 7:30 PM

Trevor Hall

33 West Street, Annapolis, MD 21401

Event Dates 4

Dec 03, 2026 8:00 PM

Jon McLaughlin

33 West Street, Annapolis, MD 21401

Event Dates 14

Dec 04, 2026 8:00 PM

Irving Berlin's Holiday Inn

1804 West Street, Annapolis, MD 21401

Event Dates 178

Dec 05, 2026 2:00 PM

S. Carey

33 West Street, Annapolis, MD 21401

Event Dates 7

Dec 08, 2026 8:00 PM

Mickey Guyton

33 West Street, Annapolis, MD 21401

Event Dates 11

Dec 09, 2026 8:00 PM

The Nutcracker

801 Chase Street, Annapolis, MD 21401

Event Dates 2174

Dec 12, 2026 1:00 PM

Carbon Leaf

33 West Street, Annapolis, MD 21401

Event Dates 14

Dec 12, 2026 3:30 PM

Marc Roberge

33 West Street, Annapolis, MD 21401

Event Dates 7

Dec 16, 2026 8:00 PM

A SQRRL! Holiday Matinee

33 West Street, Annapolis, MD 21401

Event Dates 1

Dec 19, 2026 12:00 PM

Navy Midshipmen Basketball

117 Decatur Road, Annapolis, MD 21402

Event Dates 12

Dec 19, 2026 2:00 PM

Steven Page

33 West Street, Annapolis, MD 21401

Event Dates 12

Dec 21, 2026 8:00 PM

Military Bowl

550 Taylor Avenue, Annapolis, MD 21401

Event Dates 1

Dec 28, 2026 2:00 PM

Frequently Asked Questions

Quick answers about Annapolis events, venues, schedules, and live entertainment.

What events are happening in Annapolis during December 2026?

Annapolis hosts concerts, sports games, comedy shows, Broadway performances, festivals, and live entertainment throughout December 2026.

Where can I find Annapolis events by date?

Use the monthly event calendar and date filters to browse concerts, sports events, comedy shows, and live performances happening across Annapolis.

Are concerts happening in Annapolis during December 2026?

Yes. Concert schedules include touring artists, arena shows, local performances, music festivals, and live entertainment events throughout Annapolis and nearby MD areas.