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

Barktoberfest Annapolis 2025

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

Atlanta Rhythm Section in Annapolis

 Sat, 06 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

Broadneck Class of 2015

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

Eastport Yacht Club Lights Parade

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

Ballet Theatre of Maryland presents "The Nutcracker"

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

CLASSIC MOVIE NIGHT at REYNOLDS TAVERN

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

Jon McLaughlin and Friends: Home For The Holidays

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

Cruise to OysterFest in St. Michaels

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

Jon McLaughlin & Friends: Home For The Holidays

 Sun, 21 Dec at 07:30 pm Rams Head On Stage

Jolly Express Cruise

 Sat, 22 Nov at 12:00 pm 1 Dock St, Annapolis, MD, United States, Maryland 21401

Lights Parade Dinner Cruise with Ken's Creative Kitchen

 Sat, 13 Dec at 05:00 pm 1 Dock St, Annapolis, MD, United States, Maryland 21401

The DeCesaris/Prout Jingle Bell Run/Walk

Sat, 06 Dec at 09:00 am Quiet Waters Park Annapolis, Md

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

Holiday Craft Fair!

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

Peter Mayer: A Stars and Promises Christmas 2025

Thu, 11 Dec at 08:00 pm Rams Head On Stage

Ballet Theatre of Maryland presents "The Nutcracker"

 Sun, 14 Dec at 04:30 pm Maryland Hall USD 17 to 72

Holiday Parenting: Navigating Challenges with Calm & Connection

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

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

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

Ballet Theatre of Maryland presents "The Nutcracker"

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

Laura Tsaggaris (Matinee)

Sat, 06 Dec at 01:00 pm Rams Head On Stage

Happy Holidays Drag Brunch

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

Eric Scott's Annual Holiday Celebration with very Special Guest Tony Denikos

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

The Milk Carton Kids: Holiday Tour 2025 w/ Humbird

 Wed, 10 Dec at 08:00 pm Rams Head On Stage

A Peter White Christmas w/ Mindi Abair & Vincent Ingala (6:30 PM)

Thu, 04 Dec at 06:30 pm Rams Head On Stage

THE SAMPLES

 Thu, 20 Nov at 07:30 pm Annapolis Smokehouse And Tavern USD 54

Evergreen Wreath Workshop

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

A Very Merry Drag Brunch

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

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

 Sun, 12 Oct at 01:00 pm 186 Prince George St, Annapolis, MD 21401-1724, United States

Maryland Day Week 2026 - filled with fun events!

 Thu, 19 Mar at 10:00 am Anne Arundel County, MD, United States, Maryland

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