Annapolis Christmas Events

Nutcracker Tea 2025

DoubleTree by Hilton Hotel Annapolis 7 Dec 2025

Pure Prairie League in Annapolis

Rams Head On Stage 5 Dec 2025

Peter White, Mindi Abair, Vincent Ingala in Annapolis

Rams Head On Stage 4 Dec 2025

Chris Isaak in Annapolis

Maryland Hall 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

Peter White, Mindi Abair, Vincent Ingala in Annapolis

Rams Head On Stage 4 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

An Annapolis Christmas

Rams Head On Stage 14 Dec 2025

Holiday Pops at Maryland Hall

Maryland Hall for the Creative Arts 19 Dec 2025

Grand Illumination Tree Lighting - Downtown Annapolis 2025

Market Space, Annapolis, MD 21401, United States 30 Nov 2025

Jon McLaughlin & Friends: Home For The Holidays

Rams Head On Stage 21 Dec 2025

Laura Tsaggaris (Matinee)

Rams Head On Stage 6 Dec 2025

Atlanta Rhythm Section at Rams Head On Stage

Rams Head On Stage 6 Dec 2025

Eastport Yacht Club Lights Parade

Historic Downtown Annapolis 13 Dec 2025

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

49 West Coffeehouse, Winebar & Gallery 15 Dec 2025

Jon McLaughlin and Friends: Home For The Holidays

Rams Head On Stage 20 Dec 2025

A Very Merry Drag Brunch

Rams Head On Stage 21 Dec 2025

Black Friday Open House and BLOWOUT Sale!

1550 Whitehall Rd., Annapolis, MD 21409 28 Nov 2025

Happy Holidays Drag Brunch

Rams Head On Stage 20 Dec 2025

A SQRRL! Holiday (Matinee)

Rams Head On Stage 20 Dec 2025

Midnight Madness West Street Artisan Holiday Market

60 West St, Annapolis, MD 21401-2434, United States 11 Dec 2025

WTF? & Old Fox Bibliophiles Book Clubs

35 Maryland Avenue, Annapolis, MD, United States, Maryland 21401 3 Dec 2025

Ballet Theatre of Maryland presents "The Nutcracker"

Maryland Hall 20 Dec 2025

A Colonial Yuletide

186 Prince George St, Annapolis, MD 21401-1724, United States 6 Dec 2025

Paula Poundstone at Rams Head On Stage

Rams Head On Stage 19 Dec 2025

PARKING: Military Bowl

Navy Marine Corps Memorial Stadium Parking Lots 26 Dec 2025

Rams Head Presents Chris Isaak - Annapolis, MD

Maryland Hall 7 Dec 2025

Annapolis Italian Christmas Market 2025

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

Chris Isaak Live On Tour

Maryland Hall 7 Dec 2025

2025 Santa Speedo Run

O'Brien's Oyster Bar & Seafood Tavern 13 Dec 2025

Peter Mayer: A Stars and Promises Christmas 2025

Rams Head On Stage 11 Dec 2025

Pure Prairie League

Rams Head On Stage 4 Dec 2025

Midnight Madness in Downtown Annapolis 2025

Downtown Annapolis 4 Dec 2025

Live Nativity

31 Roscoe Rowe Blvd, Annapolis, MD, United States, Maryland 21401 6 Dec 2025

A Peter White Christmas at Rams Head On Stage

Rams Head On Stage 4 Dec 2025

The Empty Pockets at Rams Head On Stage

Rams Head On Stage 3 Dec 2025

5th Annapolis Santa Stroll from Peake Social!

Annapolis 6 Dec 2025

7th Annual Christmas Tree Lighting

Cape St. Claire 30 Nov 2025

Mindi Abair & Vincent Ingala

Rams Head On Stage 3 Dec 2025

A Peter White Christmas With Mindi Abair & Vincent Ingala

Rams Head On Stage 3 Dec 2025

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

Maryland Hall for the Creative Arts 13 Dec 2025

2025 Christmas Gathering

DoubleTree by Hilton Hotel Annapolis 13 Dec 2025

Live Arts Maryland Presents Handel's Messiah

St. Anne's Parish 20 Sep 2025

Pure Prairie League at Rams Head On Stage

Rams Head On Stage 5 Dec 2025

An Annapolis Christmas

Rams Head On Stage 16 Dec 2025

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

Rams Head On Stage 4 Dec 2025

Hanging of the Greens

Stan and Joe's Saloon 6 Dec 2025

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

The Spice & Tea Exchange of Annapolis 18 Dec 2025

Ballet Theatre of Maryland: The Nutcracker

Maryland Hall For The Creative Arts 12 Dec 2025

Evergreen Wreath Workshop

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

Carbon Leaf at Rams Head On Stage

Rams Head On Stage 12 Dec 2025

Son Little w/ Candi Jenkins

Rams Head On Stage 2 Dec 2025

Chris Isaak at Maryland Hall for the Creative Arts

Maryland Hall for the Creative Arts 7 Dec 2025

Holiday Tasting Event

1410 Forest Dr, Annapolis, MD, United States, Maryland 21403 6 Dec 2025

Ballet Theatre of Maryland presents "The Nutcracker"

Maryland Hall 14 Dec 2025

Carbon Leaf

Rams Head On Stage 12 Dec 2025

Tab Benoit at Rams Head On Stage

Rams Head On Stage 7 Dec 2025

Military Bowl

Navy Marine Corps Memorial Stadium 26 Dec 2025

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

St. John's College 13 Dec 2025

Christmas - closed

155 Main St, Annapolis, MD 21401 25 Dec 2025

The Gather & Give Holiday Market: A Hallmark-Inspired Holiday Fundraiser for Life of Joy Foundation

201A Ridgely Ave , Annapolis, MD, United States, Maryland 21401 13 Dec 2025

Spin It Again at NABSD 10th Annual Brigade Holiday Market

Dahlgren Hall - United States Naval Academy 9 Dec 2025

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

St. John's College 18 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

Peter White Christmas

Rams Head On Stage 4 Dec 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