Annapolis Holiday Events
Holiday events Happening Next in Annapolis, MD
Pure Prairie League in Annapolis
Rams Head On Stage
5 Dec 2025
ART
Peter White, Mindi Abair, Vincent Ingala in Annapolis
Rams Head On Stage
4 Dec 2025
CONCERTS
Atlanta Rhythm Section in Annapolis
Rams Head On Stage
6 Dec 2025
CONCERTS
CLASSIC MOVIE NIGHT at REYNOLDS TAVERN
7 Church Cir, Annapolis, MD, United States, Maryland 21401
12 Oct 2025
ENTERTAINMENT
Broadneck Class of 2015
Metropolitan Kitchen & Lounge
29 Nov 2025
WORKSHOPS
USD 66
Eastport Yacht Club Lights Parade
Historic Downtown Annapolis
13 Dec 2025
PARADES
Ballet Theatre of Maryland presents "The Nutcracker"
Maryland Hall
20 Dec 2025
ART
USD 47 TO 72
Happy Holidays Drag Brunch
Rams Head On Stage
20 Dec 2025
BRUNCH
Jon McLaughlin and Friends: Home For The Holidays
Rams Head On Stage
20 Dec 2025
TRIPS-ADVENTURES
Holiday Craft Fair!
1601 Pleasant Plains Rd, Annapolis, MD, United States, Maryland 21409
22 Nov 2025
CHRISTMAS-MARKETS-AND-FAIRS
Cruise to OysterFest in St. Michaels
1 Dock St, Annapolis, MD, United States, Maryland 21401
25 Oct 2025
MUSIC
Midnight Madness in Downtown Annapolis 2025
Downtown Annapolis
4 Dec 2025
HOLIDAY
Annapolis Chocolate Binge Festival
53 West St, Annapolis, MD 21401-2420, United States
7 Dec 2025
MUSIC
The Brit Pack at Rams Head On Stage
Rams Head On Stage
22 Nov 2025
TRIPS-ADVENTURES
Peter Mayer: A Stars and Promises Christmas 2025
Rams Head On Stage
11 Dec 2025
MUSIC
Holiday Pops at Maryland Hall
Maryland Hall for the Creative Arts
19 Dec 2025
MUSIC
Holiday Parenting: Navigating Challenges with Calm & Connection
2158 Renard Ct
13 Nov 2025
HEALTH-WELLNESS
FREE
Ballet Theatre of Maryland presents "The Nutcracker"
Maryland Hall
14 Dec 2025
ART
USD 17 TO 72
Jolly Express Cruise
1 Dock St, Annapolis, MD, United States, Maryland 21401
22 Nov 2025
HOLIDAY
Jon McLaughlin & Friends: Home For The Holidays
Rams Head On Stage
21 Dec 2025
ENTERTAINMENT
Lights Parade Dinner Cruise with Ken's Creative Kitchen
1 Dock St, Annapolis, MD, United States, Maryland 21401
13 Dec 2025
ENTERTAINMENT
Nutcracker Tea 2025
DoubleTree by Hilton Hotel Annapolis
7 Dec 2025
ART
Laura Tsaggaris (Matinee)
Rams Head On Stage
6 Dec 2025
MUSIC
The Milk Carton Kids: Holiday Tour 2025 w/ Humbird
Rams Head On Stage
10 Dec 2025
MUSIC
Eric Scott's Annual Holiday Celebration with very Special Guest Tony Denikos
49 West Coffeehouse, Winebar & Gallery
15 Dec 2025
MUSIC
Mr. Paca’s Garden Storytime: “Duck or Turkey” by Jacqueline Jules
186 Prince George St, Annapolis, MD 21401-1724, United States
15 Nov 2025
THANKSGIVING
THE SAMPLES
Annapolis Smokehouse And Tavern
20 Nov 2025
USD 54
A Peter White Christmas w/ Mindi Abair & Vincent Ingala (6:30 PM)
Rams Head On Stage
4 Dec 2025
MUSIC
The DeCesaris/Prout Jingle Bell Run/Walk
Quiet Waters Park Annapolis, Md
6 Dec 2025
SPORTS
Evergreen Wreath Workshop
1223 River Bay Road, Annapolis, MD, United States, Maryland 21409
2 Dec 2025
WORKSHOPS
A SQRRL! Holiday (Matinee)
Rams Head On Stage
20 Dec 2025
HOLIDAY
Ballet Theatre of Maryland presents "The Nutcracker"
Maryland Hall
14 Dec 2025
ART
USD 17 TO 72
A Very Merry Drag Brunch
Rams Head On Stage
21 Dec 2025
BRUNCH
Speaker: The How of WOW!!! by Karl Gercens, Longwood Gardens Conservatory Manager
1223 River Bay Road, Annapolis, MD, United States, Maryland 21409
4 Nov 2025
TRIPS-ADVENTURES
Nutcracker Storytime at the William Paca Garden Featuring the Ballet Theatre of Maryland
186 Prince George St, Annapolis, MD 21401-1724, United States
12 Oct 2025
ART
Maryland Day Week 2026 - filled with fun events!
Anne Arundel County, MD, United States, Maryland
19 Mar 2026
Ballet Theatre of Maryland IN PERSON 2025-2026 Season Subscriptions
Maryland Hall
17 Oct 2025
ART
USD 120 TO 192
2025 Lights on the Bay MD with the SPCA of Anne Arundel County
Sandy Point State Park
23 Nov 2025
HOLIDAY
USD 23 TO 100
Mini Performance of The Nutcracker by Ballet Theatre of Maryland
Maryland Hall
10 Dec 2025
ART
USD 12
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Annapolis Events
Annapolis Holiday Events