Annapolis Holiday events

Holiday events in Annapolis Today

Discover the best Holiday events in Annapolis! From festive Christmas markets to New Year's Eve fireworks displays & Holiday Bazaar, we have something for everyone. Explore the Annapolis's winter attractions and make lasting memories with friends and family. With so much to do in Annapolis, you'll never have a dull moment this holiday season.

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Holiday events in Annapolis Today

Holiday events in Annapolis Today

Fri, 26 Dec, 2025 - 12:00 PM

Jolly Express Cruise

1 Dock St, Annapolis, MD, United States, Maryland 21401
Fri, 26 Dec, 2025 - 07:00 PM

Holiday Candlelight Stroll

188 Main St, Annapolis, MD 21401-2008, United States

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Holiday events from nearby cities

Sat, 10 Jan • 02:00 PM

Winter & New Year Fest

Wheaton High School

107+ Interested

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Free
Sat, 27 Dec • 02:00 PM

The Washington Ballet's Nutcracker

Warner Theatre

15+ Interested
Sat, 27 Dec • 07:00 PM

The Washington Ballet's Nutcracker

Warner Theatre

16+ Interested
Sun, 28 Dec • 01:00 PM

The Washington Ballet's Nutcracker

Warner Theatre

8+ Interested
Sun, 04 Jan • 01:00 PM

Dr. Seuss' How the Grinch Stole Christmas! The Musical (Touring)

Broadway at The National

41+ Interested
Sun, 15 Feb • 06:00 PM

Mardi Gras at Dauphine's

Dauphine’s

USD 141
Mon, 19 Jan • 11:00 AM

2026 MLK Holiday DC Annual Peace Walk & Parade

Martin Luther King Junior Avenue Southeast

Free
Mon, 29 Dec • 07:00 PM

How the Grinch Stole Christmas

National Theatre - DC
Fri, 26 Dec • 10:00 PM

The Day After Christmas - Afrobeats Party W/ OPEN BAR

Rosebar Lounge

Free

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