The Annapolis Holiday Market is packing up its usual waterfront home and setting up at Annapolis Mall this December, with organizers scheduling two separate weekends of shopping, food and entertainment while City Dock remains under construction. The fifth annual market will run Dec. 4 through 6 and again Dec. 11 through 13, 2026, with free admission on every day of both weekends.
According to annapolisholidaymarket.com, organizers say the market is now in its fifth year and that this time around, “we are at Annapolis Mall while the city dock is under renovation.” As reported by Eye On Annapolis, the move follows ongoing construction at City Dock that has displaced the event from its traditional downtown footprint.
This isn't the market's first detour. The 2025 edition relocated from City Dock to the front lawn of St. John's College and also expanded to two weekends, per the same account from the prior year, which noted the market drew roughly 100 vendors, specialty food stalls and festive entertainment, with free admission on all days. That 2025 setup sat near a parking garage offering more than 700 free spaces on weekday evenings and all day on weekends.
Vendor Numbers in Dispute
Exactly how many artisans will show up this December depends on which source you check. Annapolisholidaymarket.com states the 2026 market will feature about 150 artisans alongside specialty holiday food vendors and holiday entertainment, while a separate listing from visitannapolis.org puts the figure at 100 artisans, specialty holiday food vendors and festive entertainment. Either way, shoppers can expect a wide range of art, crafts, specialty foods and handmade gifts from local and regional makers, according to the market's own site.
The address for this year's event is 1040 Annapolis Mall Road in Annapolis, Maryland.
Food, Drink and a Still-Developing Lineup
Typical market fare includes hot chocolate, hot apple cider, spiced wine, strudels, German sausages and pretzels, per annapolisholidaymarket.com. Entertainment is still coming together for 2026; the market's own entertainment page states plainly, “We are just starting to build out our entertainment schedule,” though it already lists performances from Indian Creek School Dance and The Cordelias Quartet, along with St. Martin's Lutheran School and Songbird Collective Artists.
The relocation comes as the City Dock redevelopment project continues to reshape downtown Annapolis. Per annapolis.gov, the project has altered public space availability, traffic circulation patterns and emergency access routes within the downtown core, with temporary modifications affecting parade routes through 2028. The city's construction FAQ also notes that a fence will go up around Susan Campbell Park after St. Patrick's festivities, marking the start of Phase One construction that includes bulkhead replacement, passive flood barriers, utility work and rebricking.
What to Expect at Annapolis Mall
For market-goers, the shift to Annapolis Mall means trading a waterfront backdrop for a more conventional retail setting during peak holiday shopping season. The market's organizers describe two full weekends of shopping, food and holiday activities as the centerpiece of this year's event, continuing a format that first emerged with the 2025 move away from City Dock.
Whether the final vendor count lands closer to 100 or 150, and which street address ultimately applies, remain open questions as December approaches. Shoppers planning a visit can expect the same free-admission structure that has carried over from last year's iteration at St. John's College.
