Annapolis Holiday Events

2026 Lights on the Bay MD with the SPCA of Anne Arundel County

Sandy Point State Park 23 Nov 2026

Annapolis Chocolate Binge Festival

53 West St, Annapolis, MD 21401-2420, United States 6 Dec 2026

Annapolis Holiday Market

Annapolis Mall 4 Dec 2026

Motown & More: A Holiday Celebration (5:00 pm)

Rams Head On Stage 5 Dec 2026

Holiday Pops with vocalist Stephanie Waters

801 Chase St Ste 204, Annapolis, MD, United States, Maryland 21401 18 Dec 2026

Annapolis Holiday Market

Annapolis Mall 4 Dec 2026

Grief Sucks: Join us to help find comfort and strength during the holidays

2158 Renard Ct 9 Nov 2026

Steven Page Formerly of Barenaked Ladies

Rams Head On Stage 21 Dec 2026

Christmas Traditions by Candlelight Tour

186 Prince George St, Annapolis, MD 21401-1724, United States 27 Nov 2026

Holiday-Ready Home Workshop: Annapolis

BED BATH & BEYOND + The Container Store 7 Nov 2026

Heroes Holiday Market

1 Riverview Avenue, Annapolis, MD 6 Dec 2026

Spend The Holidays Singing!

119 S Villa Ave, Annapolis, MD, United States, Maryland 21401 6 Nov 2026

FriendsGiving Fall Out

Log Rhythm Records 21 Nov 2026

Annual Holiday Celebration with the Eric Scott Trio

49 West Coffeehouse, Winebar & Gallery 21 Dec 2026

2026 FRA 24 Holiday Party

Fleet Reserve Club Of Annapolis 5 Dec 2026

Voices of the Season

Eastport United Methodist Church 13 Dec 2026

Black Friday & Small Business Saturday @ The Spice & Tea Exchange of Annapolis

The Spice & Tea Exchange of Annapolis 27 Nov 2026

Christmas Wreath Workshop

AND Creative Studio 11 Dec 2026

Shop MeneelyBelle at Broadneck High School's 42nd Annual Holiday Craft Bazaar!

Broadneck High School 1265 Green Holly Drive Annapolis 21409 5 Dec 2026

Holiday Shopping & Community Meetup at HomeSense Annapolis

Homesense 6 Dec 2026

Winter Wonderjam

Dark Horse Annapolis 28 Nov 2026

East of Maui Santa Paddle

Truxton Park Boat Ramp 19 Dec 2026

Mickey Guyton & Friends Holiday Tour (6:00pm)

Rams Head On Stage 9 Dec 2026

AND Creative Film Club (December) - Rare Exports, A Christmas Tale (2010)

AND Creative Studio 18 Dec 2026

Heroes & Helpers: Holiday Shop with a Cop

Outback Steakhouse (2207 Forest Drive, Annapolis, MD) 5 Dec 2026

Breakfast with Santa at Historic Inns of Annapolis

The Governor Calvert House at Historic Inns of Annapolis 12 Dec 2026

Holiday DIY Workshop - 55+ Event (Open to family & friends)

The Penny at Annapolis Town Center Welcome Center 16 Dec 2026

Mini Performance of The Nutcracker by Ballet Theatre of Maryland

Maryland Hall 9 Dec 2026

Christmas Traditions by Candlelight at the William Paca House

186 Prince George St, Annapolis, MD 21401-1724, United States 27 Nov 2026

A Festive Holiday Candlelight Experience in Annapolis, MD - Thursday, December 17th

Unitarian Universalist Church of Annapolis 17 Dec 2026

Getting Together: Holiday Happy Hour

Maggiano's (Annapolis) 2 Dec 2026

Annapolis Jazz and Roots Festival - Muneer Nasser Band Jazz Genius: Coltrane, Miles & Weston ​

St. Luke's Eastport 6 Nov 2026

Irving Berlin's Holiday Inn

Main Stage At Classic Theatre of Maryland 24 Dec 2026

Annapolis Italian Christmas Market

620 Ridgely Avenue , Annapolis, MD, United States, Maryland 21401 6 Dec 2026

Williamsburg Medallion Workshop

111 Chinquapin Round Road (suite 200), Annapolis, MD, United States, Maryland 21401 8 Dec 2026

Nature Christmas Ornaments (parent and child)

111 Chinquapin Round Road (suite 200), Annapolis, MD, United States, Maryland 21401 21 Nov 2026

A SQRRL! Holiday (Matinee)

Rams Head On Stage 19 Dec 2026

Holiday Drag Brunch (Matinee)

Rams Head On Stage 20 Dec 2026