The next major event on the local art calendar is approaching as the Winter Park Sidewalk Art Festival prepares to celebrate its 66th year, March 21-23.
The festival is one of the nation’s oldest and most prestigious juried fine art shows, boasting a total of $76,500 in cash prizes that includes 10 awards of excellence, 20 awards of distinction, and 30 awards of merit. The all-volunteer board oversees a 12-month preparation process with priorities ranging from screening applications and interviewing prospective judges to arranging the floor plan of artist tents that will spread throughout Central Park.
The 2025 list of 220 artists was chosen from more than 1,000 national and international applications. Aside from the competition for cash awards, there are opportunities for participating artists to be represented in two major collections.
The City of Winter Park sponsors the Best of Show purchase award with pieces spanning the festival’s history exhibited at City Hall, Winter Park Library, and other locations. The collection is accessible through an interactive locator map on the Public Art Collection web page. The Edyth Bush Charitable Foundation has its own purchase award with winners joining The Art of Philanthropy collection, exhibited throughout the foundation headquarters at 199 S. Knowles Ave.
While the event is known as a visual arts festival, the performing arts also play a major role. The Friday Night Concert at Central Park Main Stage has been the traditional kickoff to the weekend and this year will feature George Porter Jr. & The Runnin’ Pardners as the headliner. The show will begin at 5:30 p.m. on Friday, March 21, with supporting act, The Brown Bag Brass Band. The weekend schedule of Central Park Main Stage performances is as follows:
Friday, March 21
- 3 p.m. Winter Park High School Band
- 5:30 p.m. Brown Bag Brass Band
- 7:30 p.m. George Porter Jr. & The Runnin’ Pardners
Saturday, March 22
- 11:00 a.m. Orlando Children’s Choir
- 12:00 p.m. Patchoulli
- 1:30 p.m. Biana Pinchuk
- 2:45 p.m. Don Soledad
- 4:15 p.m. Greg Seel
Saturday, March 23
- 10 a.m. Paint It Black
- 11:30 a.m. Arts for All
- 12:30 p.m. Flint Blade
- 2 p.m. David Gilmore
- 3:30 p.m. Michael Andrew and Swingerhead
Festival events also include kids’ activities, food and beverage vendors, and art displays by local students. The Leon Theodore Schools Exhibit includes more than 2,500 pieces from over 100 Orange County public and private schools that are juried by three local judges. And the estimated weekend attendance of 250,000 is a major economic driver for the downtown shopping and dining district. Art-inspired retail window treatments, restaurant specials, and a weekend-long sidewalk sale accompany the festival schedule.
Residents and guests are reminded of the following street closures that are in effect during festival weekend:
- Garfield Avenue
- Lincoln and East Welbourne Avenues, from Center Street to Park Avenue
- Morse Boulevard, from South Knowles to South New York Avenues
- New England Avenue from West Park Avenue to Center Street
- Park Avenue from West Canton to Lyman Avenues
Festival hours will be 9 a.m.-6 p.m. on March 21-22, and 9 a.m.-5 p.m. on March 23. Guests are advised that no pets, bicycles, motorized scooters or skateboards will be allowed inside the festival areas. Click here for photos from the 2024 Winter Park Sidewalk Art Festival. For more information, scheduling updates, and to view a gallery of 2025 participating artists, visit WPSAF.org.