Holiday events in Annapolis

Check out happening holiday events all around Annapolis, MD

Ballet Theatre of Maryland presents "The Nutcracker"

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

Holiday Improv Comedy Show - Annapolis Maryland

 Sat, 20 Dec at 08:00 pm ArtFarm USD 10

A Very Merry Drag Brunch

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

Holiday Virtual Charity Wine Dinner

 Sun, 14 Dec at 06:00 pm 36 West St, Annapolis, MD, United States, Maryland 21401

Midnight Madness in Downtown Annapolis 2025

 Thu, 18 Dec at 04:00 pm Downtown Annapolis

Jon McLaughlin and Friends: Home For The Holidays

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

Happy Holidays Drag Brunch

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

Breathwork Amongst the Holiday Chaos with Gillian

 Tue, 16 Dec at 07:00 pm lululemon Free

WINTER SOLSTICE CELEBRATION & SOUNDBATH

 Sun, 21 Dec at 04:30 pm Wellsview Cottage: Center for Holistic and Integrative Health Free

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

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

Restorative Yoga with Chelsea

 Tue, 16 Dec at 06:30 pm lululemon Free

Ballet Theatre of Maryland presents "The Nutcracker"

 Sun, 21 Dec at 04:30 pm Maryland Hall USD 17 to 72

Holiday Pops at Maryland Hall

 Fri, 19 Dec at 07:30 pm Maryland Hall for the Creative Arts

Artist-led tour of Sacred Spaces with Jabari Jefferson

 Sat, 20 Dec at 12:00 pm Banneker-Douglass-Tubman Museum Free

Songs of the Season - a holiday concert and sing-along

 Sun, 14 Dec at 03:00 pm Eastport United Methodist Church USD 0 to 12

Jon McLaughlin & Friends: Home For The Holidays with T.3

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

Dalton Connection Celebration & Networking Night

 Thu, 18 Dec at 06:30 pm Acqua al 2 - Annapolis Free

Family Art Night: Holiday Cards

Fri, 19 Dec at 05:30 pm 111 Chinquapin Round Road (suite 200), Annapolis, MD, United States, Maryland 21401

Vintage Vibe Finds private holiday shopping experience

 Sun, 14 Dec at 07:00 pm 40 Hudson St unit 107 USD 15

Live Arts Maryland Presents Handel's Messiah

 Sun, 21 Dec at 03:00 pm St. Anne's Parish USD 0 to 39

Annapolis Firefighter’s Santa Run

 Sun, 14 Dec at 05:00 pm 914 Bay Ridge Ave, Annapolis, MD

Indian Creek Annual Holiday Gathering

 Fri, 19 Dec at 06:00 pm Pearl Restaurant

A SQRRL! Holiday at Rams Head On Stage

 Sat, 20 Dec at 12:00 pm Rams Head On Stage

🎁 11th Hour Holiday Shopping at The Spice & Tea Exchange of Annapolis! 🎁

 Thu, 18 Dec at 04:00 pm The Spice & Tea Exchange of Annapolis

Midnight Madness

 Thu, 18 Dec at 05:00 pm 35 Maryland Avenue, Annapolis, MD, United States, Maryland 21401

Heroes Holiday Market

 Sun, 14 Dec at 08:00 am 1 Riverview Avenue, Annapolis, MD

Cookies & Cocoa at The Hub at Bread and Butter Kitchen

 Sat, 20 Dec at 03:00 pm 303 Second St suite b USD 23 to 39

Ballet Theatre of Maryland presents "The Nutcracker"

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

Ballet Theatre of Maryland presents "The Nutcracker"

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

Happy Holidays Drag Brunch at Rams Head On Stage

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

Grounding in Grace: A Cacao Ceremony with Sound Therapy

 Sun, 14 Dec at 12:00 pm Quiet Waters Park USD 20 to 37

WTF? & Old Fox Bibliophiles Book Clubs

 Thu, 18 Dec at 07:00 pm 35 Maryland Avenue, Annapolis, MD, United States, Maryland 21401

SQRRL! HOLIDAY! Kids Musical Extravaganza! MATINEE SHOW w/ The Christmas Wish Crackler!

 Sat, 20 Dec at 12:00 pm Rams Head On Stage

We Lead Volume 3 Author Signing @ HERE. a pop-up shop!

 Mon, 15 Dec at 06:00 pm 6 Fleet St, Annapolis, MD 21401-1712, United States

Holiday Ceramic Lantern Party @ NEO Pizza Annapolis /Maryland Craft Parties

 Tue, 16 Dec at 06:00 pm Neo Pizza Annapolis USD 47

Run Naptown Running Festival

 Sat, 20 Dec at 07:00 am Navy-Marine Corps Stadium

Bay Winds Band Holiday Winter Concert "Set the Scene" with Holiday Fun!

 Tue, 16 Dec at 07:30 pm Unity by the Bay (Maryland)

A SQRRL! Family Holiday Show

 Sat, 20 Dec at 05:00 pm Rams Head On Stage - Annapolis

Christmas - closed

 Thu, 25 Dec at 10:00 am 155 Main St, Annapolis, MD 21401

Teacher and Staff Luncheon

 Mon, 15 Dec at 12:00 pm Annapolis Senior High

Santa Run & Toy Drive

 Sun, 14 Dec at 03:45 pm Hunt Meadow Pool

ANNAPOLIS HOLIDAY MARKET w/ SANTA & The Wish Crackler - St. John's College - Annapolis, Maryland

 Thu, 18 Dec at 04:00 pm St. John's College

4th Annual Peake Irish Experience for Annapolis St Patrick's Day on 3/7

 Sat, 07 Mar at 12:00 pm Main Street USD 7 to 29

Maryland Day Celebration 2026 - filled with fun events!

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

Winter "Labyrinth of Light" Walk - Open Daily Till March

 Wed, 10 Dec at 04:30 pm Wellsview Cottage: Center for Holistic and Integrative Health Free

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