Annapolis Holiday Events

Ballet Theatre of Maryland presents "The Nutcracker"

Maryland Hall 20 Dec 2025

Holiday Improv Comedy Show - Annapolis Maryland

ArtFarm 20 Dec 2025

A Very Merry Drag Brunch

Rams Head On Stage 21 Dec 2025

Midnight Madness in Downtown Annapolis 2025

Downtown Annapolis 18 Dec 2025

Jon McLaughlin and Friends: Home For The Holidays

Rams Head On Stage 20 Dec 2025

Happy Holidays Drag Brunch

Rams Head On Stage 20 Dec 2025

WINTER SOLSTICE CELEBRATION & SOUNDBATH

Wellsview Cottage: Center for Holistic and Integrative Health 21 Dec 2025

Handel's Messiah - Annapolis Chorale and Orchestra

St. Anne's Episcopal Church - Annapolis Maryland 20 Dec 2025

Ballet Theatre of Maryland presents "The Nutcracker"

Maryland Hall 21 Dec 2025

Holiday Pops at Maryland Hall

Maryland Hall for the Creative Arts 19 Dec 2025

Artist-led tour of Sacred Spaces with Jabari Jefferson

Banneker-Douglass-Tubman Museum 20 Dec 2025

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

Rams Head On Stage 21 Dec 2025

Dalton Connection Celebration & Networking Night

Acqua al 2 - Annapolis 18 Dec 2025

2nd Generation @ Dark Horse!

985 Bay Ridge Rd, Annapolis, MD 21403-3934, United States 26 Dec 2025

Family Art Night: Holiday Cards

111 Chinquapin Round Road (suite 200), Annapolis, MD, United States, Maryland 21401 19 Dec 2025

Indian Creek Annual Holiday Gathering

Pearl Restaurant 19 Dec 2025

Live Arts Maryland Presents Handel's Messiah

St. Anne's Parish 21 Dec 2025

A SQRRL! Holiday at Rams Head On Stage

Rams Head On Stage 20 Dec 2025

Breathwork Amongst the Holiday Chaos with Gillian

lululemon 16 Dec 2025

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

The Spice & Tea Exchange of Annapolis 18 Dec 2025

Midnight Madness

35 Maryland Avenue, Annapolis, MD, United States, Maryland 21401 18 Dec 2025

Cookies & Cocoa at The Hub at Bread and Butter Kitchen

303 Second St suite b 20 Dec 2025

Restorative Yoga with Chelsea

lululemon 16 Dec 2025

Happy Holidays Drag Brunch at Rams Head On Stage

Rams Head On Stage 21 Dec 2025

WTF? & Old Fox Bibliophiles Book Clubs

35 Maryland Avenue, Annapolis, MD, United States, Maryland 21401 18 Dec 2025

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

Rams Head On Stage 20 Dec 2025

Run Naptown Running Festival

Navy-Marine Corps Stadium 20 Dec 2025

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

Neo Pizza Annapolis 16 Dec 2025

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

Unity by the Bay (Maryland) 16 Dec 2025

A SQRRL! Family Holiday Show

Rams Head On Stage - Annapolis 20 Dec 2025

Christmas - closed

155 Main St, Annapolis, MD 21401 25 Dec 2025

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

St. John's College 18 Dec 2025

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

Main Street 7 Mar 2026

Maryland Day Celebration 2026 - filled with fun events!

Across Annapolis & Anne Arundel County, MD, United States, Maryland 19 Mar 2026

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

Wellsview Cottage: Center for Holistic and Integrative Health 10 Dec 2025

Ballet Theatre of Maryland IN PERSON 2025-2026 Season Subscriptions

Maryland Hall 17 Oct 2025

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

Sandy Point State Park 23 Nov 2025

Mini Performance of The Nutcracker by Ballet Theatre of Maryland

Maryland Hall 10 Dec 2025