Annapolis Holiday Market 2026

The Annapolis Holiday Market is an outdoor Christmas-style artisan market in Annapolis, Maryland, returning for its fifth year on December 4–6 and December 11–13, 2026. It combines handmade holiday shopping, seasonal food and drinks, and live entertainment, with roughly 150 artisans expected.

Dates, hours, and location

The 2026 market moves to a new location outside Annapolis Mall, at 1040 Annapolis Mall Road near West Street and Jennifer Road, while City Dock undergoes construction. Hours are 11 a.m.–9 p.m. Friday and Saturday and 11 a.m.–7 p.m. Sunday on both weekends; admission and parking are free.

What to shop for

The emphasis is on original, handmade work rather than resale merchandise. Expected offerings span jewelry, ceramics, glass, textiles, woodworking, paintings and photography, home décor, ornaments, wreaths, candles, and other giftable crafts, alongside specialty-food makers; the organizer’s vendor rules specifically exclude new vendors selling resale goods.

Food and atmosphere

The market follows the Kris Kringle/European Christmas-market concept, pairing shopping with seasonal treats such as hot chocolate, hot cider, strudel, pretzels, German sausages, and spiced wine. Live entertainment runs during the event, with the 2026 performance schedule still being expanded as of early November.

Part of Annapolis at Christmas

The two weekends overlap with several other Annapolis traditions, making the market part of a broader holiday season rather than an isolated craft fair. Nearby 2026 events include Midnight Madness on December 3, 10, and 17, the Annapolis Chocolate Binge Festival on December 6, and the Eastport Yacht Club Lights Parade on December 12.