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Annapolis Holiday Market 2026

Showcase your art in Annapolis, Maryland, December 4 to 6 and December 11 to 13, 2026. The Annapolis Holiday Market is open Friday and Saturday and is located next to Annapolis Mall, which gets between 20,000 and 35,000 visitors per day. Join the 5th annual Annapolis Holiday Market with other artisans, crafters, and holiday food makers for a fun and festive holiday market that includes live daily entertainment. It's located in a highly visible location near the intersection of Route 50, West Street, and Jennifer Road in the parking lot of Annapolis Mall, a thriving regional shopping destination that will keep the foot traffic coming. The Crowne Plaza Hotel is located across the street, and about a dozen hotels are located within a 3-mile radius. Annapolis serves as the State capital, home to the US Naval Academy, a regional hospital, and a gateway to the Chesapeake Bay, so there is a steady flow of tourists, employees, and locals in the area.