2026 holiday season

Christmas & Holiday Craft Fairs in Annapolis, MD

5 holiday markets, Christmas bazaars, and craft shows in Annapolis from Nov 21, 2026 through Christmas Eve.

Holiday Fairs

Nov 21

First Event

142

Across Maryland

Every craft fair and market from November 1 through Christmas Eve is listed, since that is when holiday shopping happens. 🎄 Holiday marks the 3 whose name says holiday.

November holiday fairs in Annapolis(1)

📅 Nov 21, 2026

Wellness Market

📍 Annapolis, MD• The Collective

A market featuring products and services focused on health and wellness.

December holiday fairs in Annapolis(4)

🎄 Holiday📅 Dec 4, 2026 - Dec 13, 2026🔁 Recurring

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.

💰 $675 - $1125⭐ Juried🌳 Outdoor

📅 Dec 6, 2026🔁 Recurring

Annapolis Chocolate Binge Festival

📍 Annapolis, MD• Downtown Annapolis

This Maryland Festival will have crafts, fine art and fine craft exhibitors, and no food booths. There will be 2 stages with Local talent and the hours will be Sun 11am-4pm. This event will also include demonstrations.

🌳 Outdoor

🎄 Holiday📅 Dec 10, 2026

Midnight Madness on West - Annapolis Holiday Market

📍 Annapolis, MD• West Street & Church Circle

An outdoor holiday market on West Street featuring festive decor, live entertainment, art vendors, and a human hamster ball run. The event takes place on Thursday nights in December.

🌳 Outdoor

🎄 Holiday📅 Dec 12, 2026

Breakfast with Santa at Historic Inns of Annapolis

📍 Annapolis, MD• The Governor Calvert House at Historic Inns of Annapolis

Celebrate the season with Breakfast with Santa, festive family fun, and a FREE Holiday Market at the Historic Inns of Annapolis!

Holiday shopping in Annapolis this season

The first Annapolis holiday fair is Wellness Market on Nov 21, 2026, and the last is Breakfast with Santa at Historic Inns of Annapolis on Dec 12, 2026. 1 is in November, and 4 in December. Venues this year include The Collective, Annapolis Mall, Downtown Annapolis.

Annapolis accounts for 5 of the 142 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.

Still accepting vendors

Annapolis Holiday Market 2026
Apply by Nov 20, 2026

More holiday fairs

Other Maryland cities

Baltimore26 fairs
Oxon Hill8 fairs
Westminster8 fairs
Frederick6 fairs
Timonium6 fairs
Gaithersburg5 fairs
Waldorf4 fairs
Boonsboro3 fairs
Bowie3 fairs
Glen Echo3 fairs

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Annapolis holiday craft fair FAQ

When are the Christmas craft fairs in Annapolis, MD in 2026?

Annapolis has 5 holiday craft fairs listed between Nov 21, 2026 and Dec 12, 2026: Wellness Market (Nov 21, 2026); Annapolis Holiday Market 2026 (Dec 4, 2026); Annapolis Chocolate Binge Festival (Dec 6, 2026); Midnight Madness on West (Dec 10, 2026); and 1 more.

Where are the holiday markets held in Annapolis?

This season's Annapolis holiday fairs are at The Collective, Annapolis Mall, Downtown Annapolis, West Street & Church Circle and 1 other venues. Each listing has the address and hours.

How do I sell at a Christmas craft fair in Annapolis?

1 of the Annapolis holiday fairs is still accepting vendors; Annapolis Holiday Market 2026 closes applications on Nov 20, 2026. Open a listing for its application link, and see the Maryland holiday page for shows in nearby towns.