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  2. Craft Fairs by State
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  4. Annapolis

Craft Fairs in Annapolis, MD 2026

Browse 6 upcoming craft fairs, art shows, and artisan markets in Annapolis, Maryland. Average booth fee: $675.

6
Upcoming
21
Total Listed
$675
Avg. Booth Fee
$675–$1125
Fee Range
4 Christmas & holiday craft fairs in Annapolis
Holiday markets and bazaars for the 2026 season, by month
→

Upcoming Craft Fairs in Annapolis

6 fairs

📅 Oct 30, 2026

Naptown Flea Halloween Night Market

📍 Annapolis, MD• GameOn bar+arcade

Shop spooky finds and local treasures at Naptown Flea’s Halloween Night Market! Everything will be $40 and under!!

📅 Nov 1, 2026

First Sunday Arts Festival - November

📍 Annapolis, MD• Downtown Annapolis

This Maryland Craft Show will have crafts, fine art and fine craft exhibitors, and 8 food booths. There will be 2 stages with Local talent and the hours will be Sun 11am-5pm. This event will also include demonstrations.

📅 Nov 21, 2026

Wellness Market

📍 Annapolis, MD• The Collective

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

📅 Dec 4, 2026 - Dec 13, 2026

Annapolis Holiday Market 2026

📍 Annapolis, MD• Annapolis Mall

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

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.

📅 Jan 8, 2027

Maryland Yuletide Weekend 2027

📍 Annapolis, MD• 210 Holiday Ct

Join us for a weekend of fun with two costume balls and a Renfaire Marketplace!

⏰ Application Deadlines

  • Annapolis Holiday Market 2026
    Apply by Nov 20, 2026

🔗 Quick Links

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⛺10x10 Canopy + SidewallsVendor pick🪑6ft Folding TableVendor pick🎨Stretch Table CoverVendor pick⚖️Tent WeightsFrom $30🌀Hanging Tent FanVendor pick📋Sign HoldersFrom $25
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📍 Other Cities in Maryland

Baltimore(39)Westminster(13)Gaithersburg(10)Oxon Hill(10)Timonium(10)Frederick(6)Columbia(5)Laurel(5)Bowie(4)Lutherville-Timonium(4)

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About Craft Fairs in Annapolis, Maryland

Annapolis hosts 21 craft fairs, art shows, and artisan markets throughout the year. Whether you're a local vendor or traveling to sell your handmade goods, TheCraftMap helps you find the best events in Annapolis with booth fee details, application deadlines, and vendor reviews.

Looking for more events? Browse all craft fairs in Maryland or use our calendar view to plan your 2026 craft fair season. Our ROI calculator can help you estimate whether a fair is worth the trip.