Annapolis Holiday Events

Pure Prairie League in Annapolis

Rams Head On Stage 5 Dec 2025

CLASSIC MOVIE NIGHT at REYNOLDS TAVERN

7 Church Cir, Annapolis, MD, United States, Maryland 21401 12 Oct 2025

Atlanta Rhythm Section in Annapolis

Rams Head On Stage 6 Dec 2025

CLASSIC MOVIE NIGHT at REYNOLDS TAVERN

7 Church Cir, Annapolis, MD, United States, Maryland 21401 28 Sep 2025

Rombauer Wine Dinner - Chart House Prime

Chart House 18 Sep 2025

CLASSIC MOVIE NIGHT at REYNOLDS TAVERN

7 Church Cir, Annapolis, MD, United States, Maryland 21401 2 Nov 2025

Annapolis Fall Italian Festa

620 Ridgely Avenue, Annapolis, MD, United States, Maryland 21401 21 Sep 2025

SAT 9/20/25: BATMAN DAY 2025 AT THIRD EYE

209 Chinquapin Round Rd, Annapolis, MD, United States, Maryland 21401 20 Sep 2025

Broadneck Class of 2015

Metropolitan Kitchen & Lounge 29 Nov 2025

CLASSIC MOVIE NIGHT at REYNOLDS TAVERN

7 Church Cir, Annapolis, MD, United States, Maryland 21401 14 Sep 2025

Eastport Yacht Club Lights Parade

Historic Downtown Annapolis 13 Dec 2025

Barktoberfest Annapolis 2025

1906 Towne Centre Blvd 4 Oct 2025

Happy Holidays Drag Brunch

Rams Head On Stage 20 Dec 2025

Holiday Parenting: Navigating Challenges with Calm & Connection

2158 Renard Ct 13 Nov 2025

Jon McLaughlin and Friends: Home For The Holidays

Rams Head On Stage 20 Dec 2025

SOFO Summer Drive-In Movies Under the Stars - September 2025

Bay Ridge Plaza 123 Hillsmere Dr, Annapolis MD 21403 26 Sep 2025

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

Rams Head On Stage 26 Dec 2025

Annapolis Chocolate Binge Festival

53 West St, Annapolis, MD 21401-2420, United States 7 Dec 2025

The Brit Pack at Rams Head On Stage

Rams Head On Stage 22 Nov 2025

Ballet Theatre of Maryland presents "The Nutcracker"

Maryland Hall 20 Dec 2025

Cruise to OysterFest in St. Michaels

1 Dock St, Annapolis, MD, United States, Maryland 21401 25 Oct 2025

A Very Merry Drag Brunch

Rams Head On Stage 21 Dec 2025

Holiday Craft Fair!

1601 Pleasant Plains Rd, Annapolis, MD, United States, Maryland 21409 22 Nov 2025

ITZALL Goode Annual Holiday Celebration with the Eric Scott Trio and Special Guests

49 West Coffeehouse, Winebar & Gallery 15 Dec 2025

Evergreen Wreath Workshop

1223 River Bay Road, Annapolis, MD, United States, Maryland 21409 2 Dec 2025

Ballet Theatre of Maryland presents "The Nutcracker"

Maryland Hall 14 Dec 2025

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

Nutcracker Storytime at the William Paca Garden Featuring the Ballet Theatre of Maryland

186 Prince George St, Annapolis, MD 21401-1724, United States 20 Oct 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