🗓️ Annual, usually March
Winter Park Sidewalk Art Festival™ 68th 2027
📍 Central Park and along Park Avenue, Winter Park, Florida
About
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.
💰 Booth Information
- Booth Fee
- $575
- Application Fee
- $45
📋 Event Details
- Expected Attendance
- 2,026
- Vendor Spots
- 218
- Application Deadline
- Sep 23, 2026
📞 Contact
🗺️ Plan Your Trip
📅 Event: Mar 19 - Mar 21 — Plan your travel accordingly!
💡 Pro Tip: Book hotels early for popular events! Consider staying nearby the night before for early setup.
📌 Quick Facts
- 📅
- Mar 19, 2027 — Mar 21, 2027
- 📍
- Winter Park, FL
- 💰
- $575
- 🏪
- 218 vendor spots
- 👥
- 2,026 expected
- ⏰
- Deadline: Sep 23, 2026
- 🏷️
- Juried · Outdoor
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