Holiday events in Annapolis

Check out happening holiday events all around Annapolis, MD

Pure Prairie League in Annapolis

 Fri, 05 Dec at 08:00 pm Rams Head On Stage

Atlanta Rhythm Section in Annapolis

 Sat, 06 Dec at 08:00 pm Rams Head On Stage

Annapolis Chocolate Binge Festival

Sun, 07 Dec at 11:00 am 53 West St, Annapolis, MD 21401-2420, United States

Nutcracker Tea 2025

Sun, 07 Dec at 10:00 am DoubleTree by Hilton Hotel Annapolis

Holiday Craft Fair!

 Sat, 22 Nov at 02:00 pm 1601 Pleasant Plains Rd, Annapolis, MD, United States, Maryland 21409

Peter White, Mindi Abair, Vincent Ingala in Annapolis

 Thu, 04 Dec at 06:30 pm Rams Head On Stage

2025 Lights on the Bay (Annapolis)

 Sat, 22 Nov at 05:00 pm Sandy Point State Park

2025 FRA 24 Holiday Party

 Sat, 06 Dec at 06:00 pm Fleet Reserve Club Of Annapolis USD 66

Holiday Parenting: Navigating Challenges with Calm & Connection

 Thu, 13 Nov at 06:00 pm 2158 Renard Ct Free

Holiday Pops at Maryland Hall

 Fri, 19 Dec at 07:30 pm Maryland Hall for the Creative Arts

The Brit Pack at Rams Head On Stage

 Sat, 22 Nov at 08:00 pm Rams Head On Stage

Jon McLaughlin & Friends: Home For The Holidays

 Sun, 21 Dec at 07:30 pm Rams Head On Stage

Vintage Vibe Finds private holiday shopping experience

 Sun, 14 Dec at 07:00 pm 40 Hudson St unit 107 USD 15

Laura Tsaggaris (Matinee)

Sat, 06 Dec at 01:00 pm Rams Head On Stage

East of Maui Santa Paddle

 Sat, 13 Dec at 10:00 am Horn Point Street End Park

Broadneck Class of 2015

 Sat, 29 Nov at 07:00 pm Metropolitan Kitchen & Lounge USD 66

Ballet Theatre of Maryland presents "The Nutcracker"

 Sun, 14 Dec at 04:30 pm Maryland Hall USD 17 to 72

18th Annual Tree Lighting

Thu, 20 Nov at 05:30 pm 1906 Towne Centre Boulevard, Annapolis, MD, United States, Maryland 21401

Annual Boxwood Wreath Making

 Sun, 07 Dec at 03:00 pm Charles Carroll House USD 50

SOD-O Holiday Party

 Sat, 06 Dec at 06:00 pm Acqua al 2 - Annapolis USD 0 to 100

Ballet Theatre of Maryland presents "The Nutcracker"

 Sat, 20 Dec at 07:00 pm Maryland Hall USD 47 to 72

Sip & Shop of Historic Annapolis

 Wed, 12 Nov at 05:00 pm The Spice & Tea Exchange of Annapolis

Annapolis Italian Christmas Market 2025

 Sun, 07 Dec at 10:00 am 620 Ridgely Avenue , Annapolis, MD, United States, Maryland 21401

Peter Mayer: A Stars and Promises Christmas 2025

Thu, 11 Dec at 08:00 pm Rams Head On Stage

Jolly Express Cruise

 Sat, 22 Nov at 12:00 pm 1 Dock St, Annapolis, MD, United States, Maryland 21401

Songs of the Season - a holiday concert and sing-along

 Sun, 14 Dec at 03:00 pm Eastport United Methodist Church USD 0 to 12

Midnight Madness in Downtown Annapolis 2025

 Thu, 04 Dec at 04:00 pm Downtown Annapolis

Lights Parade Dinner Cruise with Ken's Creative Kitchen

 Sat, 13 Dec at 05:00 pm 1 Dock St, Annapolis, MD, United States, Maryland 21401

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

 Fri, 28 Nov at 09:00 am 209 Chinquapin Round Rd, Annapolis, MD, United States, Maryland 21401

Lunch with The Grinch

 Sun, 07 Dec at 10:00 am California Pizza Kitchen at Annapolis Free

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

 Mon, 15 Dec at 07:30 pm 49 West Coffeehouse, Winebar & Gallery

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

 Sat, 15 Nov at 10:00 am 186 Prince George St, Annapolis, MD 21401-1724, United States

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

 Sat, 13 Dec at 11:00 am St. John's College

Annual Kwanzaa Celebration

 Sat, 13 Dec at 10:00 am 84 Franklin St, Annapolis, MD, United States, Maryland 21401

A SQRRL! Holiday (Matinee)

Sat, 20 Dec at 12:00 pm Rams Head On Stage

A Very Merry Drag Brunch

Sun, 21 Dec at 12:30 pm Rams Head On Stage

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

Thu, 04 Dec at 06:30 pm Rams Head On Stage

THE SAMPLES

 Thu, 20 Nov at 07:30 pm Annapolis Smokehouse And Tavern USD 54

Happy Holidays Drag Brunch

 Sat, 20 Dec at 07:00 pm Rams Head On Stage

The DeCesaris/Prout Jingle Bell Run/Walk

Sat, 06 Dec at 09:00 am Quiet Waters Park Annapolis, Md

Ballet Theatre of Maryland presents "The Nutcracker"

 Sun, 21 Dec at 04:30 pm Maryland Hall USD 17 to 72

Jon McLaughlin and Friends: Home For The Holidays

 Sat, 20 Dec at 07:00 pm Rams Head On Stage

Bubbles & Baubles

 Wed, 03 Dec at 05:30 pm Wrabyn Boutique USD 162

Ballet Theatre of Maryland presents "The Nutcracker"

 Sun, 14 Dec at 01:00 pm Maryland Hall USD 17 to 72

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

 Wed, 26 Nov at 11:00 am 209 Chinquapin Round Rd, Annapolis, MD, United States, Maryland 21401

Spin It Again at NABSD 10th Annual Brigade Holiday Market

 Tue, 09 Dec at 10:00 am Dahlgren Hall - United States Naval Academy

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

 Thu, 18 Dec at 04:00 pm St. John's College

A SQRRL! Family Holiday Show

 Sat, 20 Dec Rams Head On Stage - Annapolis

Maryland Day Week 2026 - filled with fun events!

 Thu, 19 Mar at 10:00 am Anne Arundel County, MD, United States, Maryland

Ballet Theatre of Maryland IN PERSON 2025-2026 Season Subscriptions

 Fri, 17 Oct at 07:30 pm Maryland Hall USD 120 to 192

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

 Sun, 23 Nov at 05:00 pm Sandy Point State Park USD 23 to 100

Mini Performance of The Nutcracker by Ballet Theatre of Maryland

 Wed, 10 Dec at 09:30 am Maryland Hall USD 12