Winter Park Sidewalk Art Festival

Winter Park Sidewalk Art Festival The Winter Park Sidewalk Art Festival has been bringing fine art to Central Florida for 67 years!

The Winter Park Sidewalk Art Festival is one of the nation’s oldest, largest and most prestigious outdoor fine arts & fine crafts festivals. Organized and run by a dedicated group of volunteers, the juried show is nationally recognized and is named the #5 Fine Art Show in the country by Sunshine Artist Magazine. The festival features all original artwork that has been designed and executed by the

exhibiting artists during the past two years. The show is conveniently located in Central Park, a beautifully landscaped area whose surrounding streets are closed during the festival to allow for foot traffic only. Many artist booths line Winter Park’s Park Avenue, the heart of a charming downtown with brick-lined streets, unique boutique shops, and multiple outdoor cafes and bistros. Attendance is expected to exceed 250,000 people for the three-day event. A panel of judges has selected 213 artists to participation this year.

We are beyond honored that the Winter Park Sidewalk Art Festival caught the eye of Linnea Bailey and Southern Living. Th...
04/20/2026

We are beyond honored that the Winter Park Sidewalk Art Festival caught the eye of Linnea Bailey and Southern Living. Thank you for shining a spotlight on our our vibrant community and the magic that happens every year right here in downtown Winter Park!

See why Winter Park, Florida is one of the South’s best train-friendly getaways, with a walkable downtown, family-friendly attractions, scenic boat tours, and easy car-free adventures just steps from the station.

A huge thank you to our 2026 Entertainment Sponsor — Orlando Health and Orlando Health Jewett Orthopedic Institute!Your ...
03/30/2026

A huge thank you to our 2026 Entertainment Sponsor — Orlando Health and Orlando Health Jewett Orthopedic Institute!

Your support helped bring Kim Waters, Michael Andrew and Swingerhead, and other live entertainment to the stage last weekend. We are so grateful to have you in our corner, helping make the festival experience truly unforgettable for thousands of art and music lovers. Thank you!

Address

P. O. Box 597
Winter Park, FL
32790

Telephone

(407) 644-7207

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