Annapolis Christmas 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

Carbon Leaf at Rams Head On Stage

Rams Head On Stage 11 Dec 2026

Brunch With The Grinch

California Pizza Kitchen at Annapolis 12 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

Mindi Abair - I Can't Wait For Christmas at Rams Head On Stage

Rams Head On Stage 6 Dec 2026

Annapolis Holiday Market

Annapolis Mall 4 Dec 2026

15th Annual Jingle Bell Run/Walk

Quiet Waters Park Rd, Annapolis, MD 21403, United States 5 Dec 2026

Steven Page Formerly of Barenaked Ladies

Rams Head On Stage 21 Dec 2026

6th Annapolis Santa Stroll from Peake Social!

Annapolis 5 Dec 2026

An Annapolis Christmas

Rams Head On Stage 14 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

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

The Great Annapolis Gingerbread Houses Contest

26 West St, Annapolis, MD 21401-2421, United States 22 Nov 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

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

Maryland Yuletide Weekend 2027

210 Holiday Ct 8 Jan 2027

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

Maryland Hall Presents: A Charlie Brown Christmas with the Eric Byrd Trio

801 Chase St, Annapolis, MD, United States, Maryland 21401 4 Dec 2026

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

209 Chinquapin Round Rd, Annapolis, MD, United States, Maryland 21401 25 Nov 2026

1776: Yuletide in Revolutionary Annapolis

186 Prince George St, Annapolis, MD 21401-1724, United States 5 Dec 2026

Atlanta Rhythm Section at Rams Head On Stage

Rams Head On Stage 21 Jan 2027

🎄 MIDNIGHT MADNESS at The Spice & Tea Exchange of Annapolis! 🎄

The Spice & Tea Exchange of Annapolis 10 Dec 2026

Maryland Hall Presents: The Holidays with Canadian Brass

801 Chase St, Annapolis, MD, United States, Maryland 21401 1 Dec 2026

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

Maryland Hall for the Creative Arts 12 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

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

A SQRRL! Holiday (Matinee)

Rams Head On Stage 19 Dec 2026