Annapolis Holiday Events

Pure Prairie League in Annapolis

Rams Head On Stage 5 Dec 2025

Nutcracker Tea 2025

DoubleTree by Hilton Hotel Annapolis 7 Dec 2025

Annapolis Chocolate Binge Festival

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

Peter White, Mindi Abair, Vincent Ingala in Annapolis

Rams Head On Stage 4 Dec 2025

Atlanta Rhythm Section in Annapolis

Rams Head On Stage 6 Dec 2025

18th Annual Tree Lighting

1906 Towne Centre Boulevard, Annapolis, MD, United States, Maryland 21401 20 Nov 2025

Holiday Parenting: Navigating Challenges with Calm & Connection

2158 Renard Ct 13 Nov 2025

50th Annual Freedom Fund Banquet

DoubleTree by Hilton (Annapolis, MD) 7 Nov 2025

Annapolis Italian Christmas Market 2025

620 Ridgely Avenue , Annapolis, MD, United States, Maryland 21401 7 Dec 2025

Holiday Pops at Maryland Hall

Maryland Hall for the Creative Arts 19 Dec 2025

Jolly Express Cruise

1 Dock St, Annapolis, MD, United States, Maryland 21401 22 Nov 2025

Lights Parade Dinner Cruise with Ken's Creative Kitchen

1 Dock St, Annapolis, MD, United States, Maryland 21401 13 Dec 2025

Laura Tsaggaris (Matinee)

Rams Head On Stage 6 Dec 2025

Holiday Craft Fair!

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

Sip & Shop of Historic Annapolis

The Spice & Tea Exchange of Annapolis 12 Nov 2025

Broadneck Class of 2015

Metropolitan Kitchen & Lounge 29 Nov 2025

A Peter White Christmas w/ Mindi Abair & Vincent Ingala (6:30 PM)

Rams Head On Stage 4 Dec 2025

SOD-O Holiday Party

Acqua al 2 - Annapolis 6 Dec 2025

Ballet Theatre of Maryland presents "The Nutcracker"

Maryland Hall 20 Dec 2025

Peter Mayer: A Stars and Promises Christmas 2025

Rams Head On Stage 11 Dec 2025

FRI 11/28/25: Black Friday MIDNIGHT MADNESS + ALL DAY DEALS At Third Eye!

209 Chinquapin Round Rd, Annapolis, MD, United States, Maryland 21401 28 Nov 2025

Jon McLaughlin & Friends: Home For The Holidays

Rams Head On Stage 21 Dec 2025

Delegate Jones's World War II Memorial Cleanup

Maryland World War II and Goldstar Family Memorial 8 Nov 2025

Mr. Paca’s Garden Storytime: “Duck or Turkey” by Jacqueline Jules

186 Prince George St, Annapolis, MD 21401-1724, United States 15 Nov 2025

Midnight Madness in Downtown Annapolis 2025

Downtown Annapolis 4 Dec 2025

The Brit Pack at Rams Head On Stage

Rams Head On Stage 22 Nov 2025

Annual Kwanzaa Celebration

84 Franklin St, Annapolis, MD, United States, Maryland 21401 13 Dec 2025

THE SAMPLES

Annapolis Smokehouse And Tavern 20 Nov 2025

A Very Merry Drag Brunch

Rams Head On Stage 21 Dec 2025

A SQRRL! Holiday (Matinee)

Rams Head On Stage 20 Dec 2025

The DeCesaris/Prout Jingle Bell Run/Walk

Quiet Waters Park Annapolis, Md 6 Dec 2025

Ballet Theatre of Maryland presents "The Nutcracker"

Maryland Hall 14 Dec 2025

Happy Holidays Drag Brunch

Rams Head On Stage 20 Dec 2025

Ballet Theatre of Maryland presents "The Nutcracker"

Maryland Hall 21 Dec 2025

Jon McLaughlin and Friends: Home For The Holidays

Rams Head On Stage 20 Dec 2025

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

49 West Coffeehouse, Winebar & Gallery 15 Dec 2025

Ballet Theatre of Maryland presents "The Nutcracker"

Maryland Hall 14 Dec 2025

WED 11/26/25: Third Eye Holiday Homecoming / Games Giving Food Drive

209 Chinquapin Round Rd, Annapolis, MD, United States, Maryland 21401 26 Nov 2025

A SQRRL! Family Holiday Show

Rams Head On Stage - Annapolis 20 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

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

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