Annapolis Christmas Events

Peter White, Mindi Abair, Vincent Ingala in Annapolis

Rams Head On Stage 4 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

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

Chris Isaak in Annapolis

Maryland Hall 7 Dec 2025

CLASSIC MOVIE NIGHT at REYNOLDS TAVERN

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

Colin Hay in Annapolis

St. John's College - Francis Scott Key Auditorium 11 Nov 2025

Eastport Yacht Club Lights Parade

Historic Downtown Annapolis 13 Dec 2025

Ballet Theatre of Maryland presents "The Nutcracker"

Maryland Hall 20 Dec 2025

Chris Isaak

Maryland Hall For The Creative Arts 6 Dec 2025

Happy Holidays Drag Brunch

Rams Head On Stage 20 Dec 2025

Peter White, Mindi Abair, Vincent Ingala in Annapolis

Rams Head On Stage 4 Dec 2025

Natalie Merchant at Maryland Hall for the Creative Arts

Maryland Hall for the Creative Arts 23 Nov 2025

Jon McLaughlin and Friends: Home For The Holidays

Rams Head On Stage 20 Dec 2025

Holiday Craft Fair!

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

Chris Isaak at Maryland Hall for the Creative Arts

Maryland Hall for the Creative Arts 7 Dec 2025

Tab Benoit at Rams Head On Stage

Rams Head On Stage 7 Dec 2025

PARKING: Military Bowl

Navy Marine Corps Memorial Stadium Parking Lots 26 Dec 2025

Paula Poundstone at Rams Head On Stage

Rams Head On Stage 19 Dec 2025

Jon McLaughlin at Rams Head On Stage

Rams Head On Stage 21 Dec 2025

Military Bowl

Navy Marine Corps Memorial Stadium 26 Dec 2025

Masquerade…The Phantom of the Opera!

Annapolis Lodge #622, 2 Pythian Drive, Edgewater, MD 21401 22 Nov 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

Carbon Leaf: 'I Want To Be Leaf' Tour 2025

Rams Head On Stage 13 Dec 2025

Pete Correale at Rams Head On Stage

Rams Head On Stage 7 Nov 2025

Natalie Merchant

Maryland Hall For The Creative Arts 22 Nov 2025

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

Maryland Hall for the Creative Arts 13 Dec 2025

The Empty Pockets at Rams Head On Stage

Rams Head On Stage 3 Dec 2025

Pure Prairie League

Rams Head On Stage 4 Dec 2025

A Peter White Christmas at Rams Head On Stage

Rams Head On Stage 4 Dec 2025

Atlanta Rhythm Section at Rams Head On Stage

Rams Head On Stage 6 Dec 2025

Ballet Theatre of Maryland presents "The Nutcracker"

Maryland Hall 14 Dec 2025

A Peter White Christmas With Mindi Abair & Vincent Ingala

Rams Head On Stage 3 Dec 2025

Paula Poundstone

Rams Head On Stage 18 Dec 2025

Ballet Theatre of Maryland: The Nutcracker

Maryland Hall For The Creative Arts 12 Dec 2025

Pure Prairie League at Rams Head On Stage

Rams Head On Stage 5 Dec 2025

Carbon Leaf at Rams Head On Stage

Rams Head On Stage 12 Dec 2025

Carbon Leaf

Rams Head On Stage 12 Dec 2025

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

49 West Coffeehouse, Winebar & Gallery 15 Dec 2025

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

Rams Head On Stage 4 Dec 2025

Evergreen Wreath Workshop

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

Parking Military Bowl

Navy-Marine Corps Memorial Stadium 27 Dec 2025

A Very Merry Drag Brunch

Rams Head On Stage 21 Dec 2025

Mindi Abair & Vincent Ingala

Rams Head On Stage 3 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

Stephen Kellogg at Rams Head On Stage

Rams Head On Stage 29 Dec 2025

Micky Dolenz at Rams Head On Stage

Rams Head On Stage 4 Nov 2025

Acoustic Alchemy

Rams Head On Stage 11 Nov 2025

Military Bowl

Navy-Marine Corps Memorial Stadium 27 Dec 2025

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

Micky Dolenz of the Monkees - Songs and Stories

Rams Head On Stage 3 Nov 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