Holiday events in Annapolis

Check out happening holiday events all around Annapolis, MD

Pure Prairie League in Annapolis

 Fri, 05 Dec at 08:00 pm Rams Head On Stage

CLASSIC MOVIE NIGHT at REYNOLDS TAVERN

 Sun, 12 Oct at 08:00 pm 7 Church Cir, Annapolis, MD, United States, Maryland 21401

Atlanta Rhythm Section in Annapolis

 Sat, 06 Dec at 08:00 pm Rams Head On Stage

CLASSIC MOVIE NIGHT at REYNOLDS TAVERN

 Sun, 28 Sep at 08:00 pm 7 Church Cir, Annapolis, MD, United States, Maryland 21401

Rombauer Wine Dinner - Chart House Prime

 Thu, 18 Sep at 07:00 pm Chart House USD 159

CLASSIC MOVIE NIGHT at REYNOLDS TAVERN

 Sun, 02 Nov at 08:00 pm 7 Church Cir, Annapolis, MD, United States, Maryland 21401

Annapolis Fall Italian Festa

 Sun, 21 Sep at 10:00 am 620 Ridgely Avenue, Annapolis, MD, United States, Maryland 21401

SAT 9/20/25: BATMAN DAY 2025 AT THIRD EYE

 Sat, 20 Sep at 11:00 am 209 Chinquapin Round Rd, Annapolis, MD, United States, Maryland 21401

Broadneck Class of 2015

 Sat, 29 Nov at 07:00 pm Metropolitan Kitchen & Lounge USD 66

CLASSIC MOVIE NIGHT at REYNOLDS TAVERN

 Sun, 14 Sep at 08:00 pm 7 Church Cir, Annapolis, MD, United States, Maryland 21401

Eastport Yacht Club Lights Parade

 Sat, 13 Dec at 06:00 pm Historic Downtown Annapolis

Barktoberfest Annapolis 2025

 Sat, 04 Oct at 11:30 am 1906 Towne Centre Blvd USD 0 to 13

Happy Holidays Drag Brunch

 Sat, 20 Dec Rams Head On Stage

Holiday Parenting: Navigating Challenges with Calm & Connection

 Thu, 13 Nov at 06:00 pm 2158 Renard Ct Free

Jon McLaughlin and Friends: Home For The Holidays

 Sat, 20 Dec at 07:00 pm Rams Head On Stage

Jimmie's Chicken Shack HOLIDAZE show at Rams Head On Stage

 Fri, 26 Dec at 07:00 pm Rams Head On Stage

Annapolis Chocolate Binge Festival

Sun, 07 Dec at 11:00 am 53 West St, Annapolis, MD 21401-2420, United States

The Brit Pack at Rams Head On Stage

 Sat, 22 Nov at 08:00 pm Rams Head On Stage

Ballet Theatre of Maryland presents "The Nutcracker"

 Sat, 20 Dec at 07:00 pm Maryland Hall USD 47 to 72

Cruise to OysterFest in St. Michaels

 Sat, 25 Oct at 09:00 am 1 Dock St, Annapolis, MD, United States, Maryland 21401

A Very Merry Drag Brunch

Sun, 21 Dec at 12:30 pm Rams Head On Stage

Holiday Craft Fair!

 Sat, 22 Nov at 02:00 pm 1601 Pleasant Plains Rd, Annapolis, MD, United States, Maryland 21409

ITZALL Goode Annual Holiday Celebration with the Eric Scott Trio and Special Guests

 Mon, 15 Dec at 07:30 pm 49 West Coffeehouse, Winebar & Gallery

Evergreen Wreath Workshop

 Tue, 02 Dec at 07:00 pm 1223 River Bay Road, Annapolis, MD, United States, Maryland 21409

Ballet Theatre of Maryland presents "The Nutcracker"

 Sun, 14 Dec at 01:00 pm Maryland Hall USD 17 to 72

Speaker: The How of WOW!!! by Karl Gercens, Longwood Gardens Conservatory Manager

 Tue, 04 Nov at 07:00 pm 1223 River Bay Road, Annapolis, MD, United States, Maryland 21409

Nutcracker Storytime at the William Paca Garden Featuring the Ballet Theatre of Maryland

 Mon, 20 Oct at 01:00 pm 186 Prince George St, Annapolis, MD 21401-1724, United States

Ballet Theatre of Maryland IN PERSON 2025-2026 Season Subscriptions

 Fri, 17 Oct at 07:30 pm Maryland Hall USD 120 to 192

2025 Lights on the Bay MD with the SPCA of Anne Arundel County

 Sun, 23 Nov at 05:00 pm Sandy Point State Park USD 23 to 100

Mini Performance of The Nutcracker by Ballet Theatre of Maryland

 Wed, 10 Dec at 09:30 am Maryland Hall USD 12