The Winter Park Sidewalk Art Festival

Event Details
Online and In-Person Event
Downtown Winter Park. FL 32789
Park Ave & Morse Blvd
Winter Park, FL 32789
United States
Pricing/Ticket Info
Event Dates and Times
Time Zone (UTC-05:00) Eastern Time (US & Canada)
Friday May 14, 2021
9:00 AM  - 06:00 PM Add to Calendar
Saturday May 15, 2021
9:00 AM  - 06:00 PM Add to Calendar
Sunday May 16, 2021
9:00 AM  - 05:00 PM Add to Calendar
The Winter Park Sidewalk Art Festival has moved this year’s Live Festival from March to May 14,15, &16, but the tradition of bringing art to Central Florida in March continues with their first ever Virtual Festival March 15 through the March 31.

The Virtual Festival will kick-off on Monday, March 15 with the 2021Poster Unveiling at 6:00 pm. The public is invited to join the event by logging onto the festival’s website at Victor Bokas, the acclaimed 2020 festival poster artist will appear to discuss his 2021 companion poster. which also features his signature, whimsical style. Both posters will be on sale on Saturday, March 20th at the Farmer’s Market in Winter Park until 1pm and at the stage in north Central Park in the afternoon.

March’s Virtual Festival gives you a preview of this year’s accepted artists that will appear live in May. It’s an opportunity to shop in advance at the artists’ on-line booths from the comfort of your home! Take part in the Scavenger Hunt as you browse and you could win original artwork and other prizes. The Virtual Festival will also include the Leon Theodore Schools Exhibit featuring amazing artwork from students throughout Orange County. The Children’s Workshop will be on-line too. Area museums will participate with virtual art projects for the kids, including craft kits that can be picked upon Saturday March 20 at the stage in Winter Park’s north Central Park and completed with on-line instructions.

The tradition continues May 14, 15, and 16 at the in-person event. The Winter Park Sidewalk Art Festival is one of the nation’s oldest and most prestigious juried fine art shows. It is ranked among the most highly regarded outdoor art shows in the nation and its artists compete for one of the largest cash awards ($74,500) among the top shows.

The Festival features original artwork that has been designed and executed by the exhibiting artists during the past two years. The show is held in historic downtown Winter Park, a beautifully landscaped area whose surrounding streets are closed during the Festival to allow for foot traffic only. Artists’ booths nestle under large oak trees in Central Park and line Park Avenue in the heart of this charming downtown with brick streets, unique boutique shops, and inviting outdoor cafes and bistros.

In keeping with COVID-19 guidelines, the event may look a little different this year, but rest assured that the Festival is taking the all of the necessary precautions to ensure a safe and successful experience for all of our artists, volunteers and art lovers.

For more information about the festival and current updates, visit the website at

The Winter Park Sidewalk Art Festival
P.O. Box 597, Winter Park, Fl, 32790
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