Annapolis Christmas Events

Ballet Theatre of Maryland presents "The Nutcracker"

Maryland Hall 20 Dec 2025

Ballet Theatre of Maryland - The Nutcracker at Maryland Hall for the Creative Arts

Maryland Hall for the Creative Arts 20 Dec 2025

A Very Merry Drag Brunch

Rams Head On Stage 21 Dec 2025

A Fright Before Christmas - Ghost Story Dinner at Middleton Tavern

Middleton Tavern 23 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

Paula Poundstone at Rams Head On Stage

Rams Head On Stage 19 Dec 2025

Holiday Pops at Maryland Hall

Maryland Hall for the Creative Arts 19 Dec 2025

Military Bowl

Navy Marine Corps Memorial Stadium 26 Dec 2025

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

Rams Head On Stage 21 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

Fireside Revelry: A Colonial Twelfth Night Concert

19 Maryland Avenue, Annapolis, MD, United States, Maryland 21401 10 Jan 2026

Women's Christmas Party

Crowne Plaza Annapolis, an IHG Hotel 20 Dec 2025

Living Nativity

1740 Forest Dr, Annapolis, MD 19 Dec 2025

A SQRRL! Holiday at Rams Head On Stage

Rams Head On Stage 20 Dec 2025

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

The Spice & Tea Exchange of Annapolis 18 Dec 2025

An Annapolis Christmas

Rams Head On Stage 16 Dec 2025

Cookies & Cocoa at The Hub at Bread and Butter Kitchen

303 Second St suite b 20 Dec 2025

A Longest Night Service

Eastport United Methodist Church 21 Dec 2025

Candlelight: Christmas Carols on Strings | Annapolis

Annapolis Waterfront Hotel 21 Dec 2025

Happy Holidays Drag Brunch at Rams Head On Stage

Rams Head On Stage 21 Dec 2025

Live Arts Maryland Presents Handel's Messiah

St. Anne's Parish 20 Sep 2025

WTF? & Old Fox Bibliophiles Book Clubs

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

PARKING: Military Bowl

Navy Marine Corps Memorial Stadium Parking Lots 26 Dec 2025

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

Rams Head On Stage 20 Dec 2025

Christmas Eve at Jack’s Fortune

Jack's Fortune Restaurant 24 Dec 2025

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

Neo Pizza Annapolis 16 Dec 2025

Christmas - closed

155 Main St, Annapolis, MD 21401 25 Dec 2025

Caroling at Oscar's

Oscar’s Coffee 24 Dec 2025

Ballet Theatre of Maryland: The Nutcracker

Maryland Hall For The Creative Arts 12 Dec 2025

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

St. John's College 18 Dec 2025

Share the Light & Joy of Christmas at St. Luke's: Christmas Day

1101 Bay Ridge Ave, Annapolis, MD, United States, Maryland 21403 25 Dec 2025

Stephen Kellogg at Rams Head On Stage

Rams Head On Stage 29 Dec 2025

Military Bowl

Navy-Marine Corps Memorial Stadium 27 Dec 2025

An Annapolis Christmas at Rams Head On Stage

Rams Head On Stage 15 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

Stephen Kellogg

Rams Head On Stage - Annapolis 30 Dec 2025

Mini Performance of The Nutcracker by Ballet Theatre of Maryland

Maryland Hall 10 Dec 2025

Share the Light & Joy of Christmas at St. Luke's: Christmas Eve

1101 Bay Ridge Ave, Annapolis, MD, United States, Maryland 21403 24 Dec 2025