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Winter Park Sidewalk Art Festival — Winter Park, Florida | TheCraftMap | TheCraftMap
  2. Craft Fairs by State
  3. Florida
  4. Winter Park
  5. Winter Park Sidewalk Art Festival
📅 Mar 20, 2026 — Mar 22, 2026

Winter Park Sidewalk Art Festival

📍 Central Park & Park Avenue - Winter Park, FL, Winter Park, Florida

⭐ Juried Show🌳 OutdoorPAST

About

The Winter Park Sidewalk Art Festival, one of the nation's most prestigious shows, is held in beautiful Central Park and along Park Avenue in historic Winter Park, FL. The show is produced by a 40-member all-volunteer board and draws crowds of up to 250,000 each year. In 2025, $76,500 was presented to artists in cash awards, including a $12,000 Best of Show purchase award, and dedicated patron purchase funds were over $90,000.

💰 Booth Information

Booth Fee
$575

📋 Event Details

Expected Attendance
2,026
Vendor Spots
215
Application Deadline
Aug 1, 2025Deadline passed

📞 Contact

✨

Contact Info

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🗺️ Plan Your Trip

🚗Get Directions🏨Find Hotels🍽️Nearby Dining⛅Check Weather

📅 Event: Mar 20 - Mar 22 — Plan your travel accordingly!

💡 Pro Tip: Book hotels early for popular events! Consider staying nearby the night before for early setup.

🛒 Gear Up for This Fair

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⛺10x10 Canopy TentFrom $89🪑6ft Folding TableFrom $45🎨Fitted TableclothFrom $15⚖️Tent WeightsFrom $35

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📌 Quick Facts

📅
Mar 20, 2026 — Mar 22, 2026
📍
Winter Park, FL
💰
$575
🏪
215 vendor spots
👥
2,026 expected
⏰
Deadline: Aug 1, 2025
🏷️
Juried · Outdoor
🌐 Visit Website📝 Apply Now