Ongoing

Annapolis Chocolate Binge Festival

Inner West Street Annapolis

About This Event A festival celebrating chocolate! The Inner West Street Association brings you the popular Annapolis Chocolate Binge Festival to downtown Annapolis for the holidays. On Sunday, December 6th […]

$6 – $70

First Sunday Arts Festival

First Sunday Arts Festival
Annapolis, 60 West St, 60 West Street, Annapolia

First Sunday Arts Festivals - Where Community and Arts FuseA monthly (May to November) street festival on the first Sunday of the month featuring 130 local and regional artisans, live […]

FREE

Elizabeth Cook (matinee)

Rams Head On Stage 33 West Street, Annapolis

Elizabeth Cook is a Nashville-based singer songwriter from Wildwood, Florida. As a critically acclaimed live act and recording artist, The New York Times lauds her “a sharp and surprising country […]

Bay Winds Band Winter Concert 2026

St. Martin's Lutheran Church 1120 Spa Road, Annapolis

Join the Bay Winds Band for their 2026 Winter Concert Series "What's in a Word" "What's in a Word."  Half and half program.  Non-holiday explores works that capture one-word ideas.  […]

Free

Mindi Abair: I Can’t Wait For Christmas

Rams Head On Stage 33 West Street, Annapolis

Mindi Abair’s I Can’t Wait For Christmas Tour is bringing the spirit of the holidays to audiences across the U.S. for an exciting, heartfelt season of music—now in its third […]