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Discover the best events and make the most of your time this month in Annapolis. From music to parenting and more, we have the biggest event range and best discovery experience, there's something for everyone.

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Ring in the New Year with Acqua al 2 at our epic New Year's Eve Celebration! Enjoy hors d'oeuvres, a live action raw bar, and a 3-hour open bar featuring handcrafted cocktails, beer, wine, and more. Dance the night away with live DJ beats from 8:45 PM to 1 AM. Don't miss out on the perfect way to welcome 2026 in style!

Wed, Dec 31st, 03:45 PMDowntown Annapolis

What's On in Annapolis

What's On in Annapolis

A SQRRL Holiday (Matinee)

Low Cut Connie with Kendra Morris

Happy Holidays Drag Brunch (16 and Over)

Jon McLaughlin

The Dirty Grass Players with The Black-Eyed Suzies

Jimmie's Chicken Shack Holidaze Show

Military Bowl: Pitt vs East Carolina

Pressing Strings

Stephen Kellogg's Old Friends Tour feat. the Kellogg Sisters

The Seldom Scene

New Year's Eve at Acqua al 2

Navy Midshipmen Mens Basketball vs. Rosemont Ravens Mens Basketball