2026 holiday season
4 holiday markets, Christmas bazaars, and craft shows in Annapolis from Nov 1, 2026 through Christmas Eve.
Every craft fair and market from November 1 through Christmas Eve is listed, since that is when holiday shopping happens. 🎄 Holiday marks the 1 whose name says holiday.
The first Annapolis holiday fair is First Sunday Arts Festival on Nov 1, 2026, and the last is Annapolis Chocolate Binge Festival on Dec 6, 2026. 2 are in November, and 2 in December. Venues this year include Downtown Annapolis, The Collective, Annapolis Mall.
Annapolis accounts for 4 of the 92 holiday fairs listed in Maryland. See the Maryland holiday craft fair list for shows within driving distance, or every Annapolis craft fair for events outside the holiday window.
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Annapolis has 4 holiday craft fairs listed between Nov 1, 2026 and Dec 6, 2026: First Sunday Arts Festival (Nov 1, 2026); Wellness Market (Nov 21, 2026); Annapolis Holiday Market (Dec 4, 2026); Annapolis Chocolate Binge Festival (Dec 6, 2026).
This season's Annapolis holiday fairs are at Downtown Annapolis, The Collective, Annapolis Mall. Each listing has the address and hours.
Most holiday shows close vendor applications one to three months out, so apply early. Open a listing for its application link, and see the Maryland holiday page for shows in nearby towns.