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  2. Craft Fairs by State
  3. Florida
  4. Winter Park

Craft Fairs in Winter Park, FL 2026

Browse 4 upcoming craft fairs, art shows, and artisan markets in Winter Park, Florida. Average booth fee: $525.

4
Upcoming
5
Total Listed
$525
Avg. Booth Fee
$425–$600
Fee Range
1 Christmas & holiday craft fair in Winter Park
See every Florida holiday market and bazaar for the 2026 season
→

Upcoming Craft Fairs in Winter Park

4 fairs

📅 Nov 14, 2026 - Nov 15, 2026🔁 Recurring

Winter Park Autumn Art Festival 53rd Annual

📍 Winter Park, FL• Central Park

The Winter Park Autumn Art Festival is a community-oriented sidewalk show that features work from over 180 outstanding Florida artists. In addition to presenting quality visual art, the festival provides free entertainment and participatory events for the enjoyment of visitors and artists. The festival is held at beautiful Central Park located along Park Avenue in downtown Winter Park and attracts 150,000 visitors. The festival is hosted by the Winter Park Chamber of Commerce.

💰 $425 - $600⭐ Juried🌳 Outdoor
📅 Jan 17, 2027

25th Annual Unity Heritage Festival | Vendor Registration

📍 Winter Park, FL• Winter Park Community Center

Register as a vendor for the 25th Annual Unity Heritage Festival, a two-day MLK Weekend community celebration in Winter Park, Florida.

📅 Mar 19, 2027 - Mar 21, 2027🔁 Recurring

Winter Park Sidewalk Art Festival™ 68th 2027

📍 Winter Park, FL• Central Park and along Park Avenue

EVENT SUMMARY The 68th Annual Winter Park Sidewalk Art Festival is one of the nation's oldest and most prestigious juried fine art shows. It consistently ranks among the most highly regarded outdoor art shows in the nation, with cash awards totaling $76,500 and dedicated Patron purchase funds expected to be over $100,000. In 2025 the festival ranked #8 in the nation in Art Fair SourceBook's top fine art festivals and was named #4 Best Show of All Times in Sunshine Artist's national poll of All Time Favorites in 2021. In 2024 the festival ranked #8 in the USA Today Readers' Choice, 10 Best Art Festivals contest. The show is located in historic downtown Winter Park, Florida, nestled throughout Central Park and stretching along Park Avenue. The event takes place on March 19 - March 21, 2027, in the heart of this charming city. Attendance at the Festival is expected to reach over 250,000 people who will view the artwork of 218 artists and 3 emerging artists.

💰 $575⭐ Juried🌳 Outdoor
📅 Mar 20, 2027

The Orlando Vintage Show

📍 Winter Park, FL• Woman's Club of Winter Park, Inc.

An authentic vintage show hosting the best of the best vintage vendors from all over the US!

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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 Florida

Miami(47)Tampa(43)Sarasota(43)Orlando(28)Naples(25)Jacksonville(24)Boca Raton(22)St. Petersburg(22)Fort Lauderdale(21)West Palm Beach(19)

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About Craft Fairs in Winter Park, Florida

Winter Park hosts 5 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 Winter Park with booth fee details, application deadlines, and vendor reviews.

Looking for more events? Browse all craft fairs in Florida 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.