Annapolis Holiday Events

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

Sandy Point State Park 23 Nov 2026

Ballet Theatre of Maryland IN PERSON 2026-2027 Season Subscriptions

Maryland Hall 16 Oct 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

Holiday Pops with vocalist Stephanie Waters

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

Steven Page Formerly of Barenaked Ladies

Rams Head On Stage 21 Dec 2026

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

Rams Head On Stage 5 Dec 2026

Annapolis Holiday Market

Annapolis Mall 4 Dec 2026

Harvest Gathering Centerpiece

244 Old Mill Bottom Rd S , Annapolis, MD, United States, Maryland 21409 28 Oct 2026

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

2158 Renard Ct 9 Nov 2026

Christmas Traditions by Candlelight Tour

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

Annual Holiday Celebration with the Eric Scott Trio

49 West Coffeehouse, Winebar & Gallery 21 Dec 2026

Spend The Holidays Singing!

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

Voices of the Season

Eastport United Methodist Church 13 Dec 2026

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

Rams Head On Stage 9 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 28 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