The Winter Park Sidewalk Art Festival is one of the nation’s oldest, largest and most prestigious outdoor art festivals. The Festival debuted in March 1960 as a community project to bring local artists and art lovers together. It is produced by an all-volunteer board and draws more than 350,000 visitors each year. Over 1,100 artists from around the world apply for the Festival each year. Festival. An independent panel of three judges selects the 225 artists who will exhibit their works. The Festival consistently ranks as one of the top juried fine art festivals in the country with high rankings in Art Fair Calendar’s “2019 Best Art Fairs”, Art Fair Source Book’s rankings, and Sunshine Artist Magazine’s “Top 100” lists. The 2021 Artists Application is by invitation only this year and is being extended to the final 2020 accepted artists.

Click here to visit the WPSAF merchandise booth! Items Available: > 2020 Poster > 2021 Poster > 2020-2021 Poster Combo > 2020 Unisex Tee > 2021 Unisex Tee > 2021 Women's Tee

Visit the Leon Theodore Schools Exhibit and enjoy a celebration of youthful creativity! The Schools Exhibit features amazing works of art by Central Florida's talented elementary, middle, and high school students from Orange County public and private schools. The Winter Park Sidewalk Art Festival has proudly showcased the artists and art programs of our local schools since the first festival in 1960. This year, we’re excited to bring the Schools Exhibit to you virtually. Middle and High School students have an opportunity to have their work judged by a panel of distinguished judges. Award winners will be announced online on Friday, March 19, 2021.

This year, the Children’s Workshop looks a little different. For the first time ever, the Children’s Workshop is going virtual! Each of the participating museums and learning centers have designed exciting crafts, projects, and activities for children to create. All the necessary supplies will be provided in project kits which will be available for pickup on the stage in North Central Park (on Park Ave. at Garfield Ave) on Saturday, March 20th between 10am and 4pm. Kids of all ages are invited to pick up project kits for any or all of the activities they’re interested in!

Art lovers of all ages are invited to visit each artist’s booth to search for hidden prizes in our Virtual Scavenger Hunt. For clues, take a good look at our 2021 WPSAF Poster, created by artist Victor Bokas, so you will be able to recognize those elements hidden throughout the Artist Marketplace. Keen eyed viewers have an opportunity to find FREE prizes including artist’s artwork and WPSAF posters. In order to claim a found prize, add the Scavenger Hunt item to your cart and “purchase” the prize (all prizes are listed for $0.00). Each prize can only be claimed once. Once a prize is “purchased” it will be listed as “out of stock”. At the conclusion of the event, found prizes will be shipped to the winners. Participants are only eligible to claim one scavenger hunt prize. Members of the WPSAF Board of Directors and their immediate families are not eligible to participate in this event.

Victor Bokas grew up against a backdrop of palm trees, beautiful beaches and sunbathers in the Florida Panhandle. These influences surface in his paintings through vibrant colors, tropical icons and a good measure of whimsy. Life’s highway later brought Victor to Central Florida in 1987 where sun, fun and exuberant energy infused his work. In many of his pieces, he pays homage to his Greek heritage. A self-described “collector of kitsch,” his studio is filled with vintage flea market finds. His collection is a source of inspiration and items from it are often incorporated into his works. Grids, squares and other graphic design elements lend structure and direction, no doubt his long career as a graphic designer ingrained a sense of order to his hyper imaginative settings. His list of accomplishments are many. Including a 15-foot x 85-foot mosaic floor for Orlando International Airport’s “A Terminal”. Designed by Victor and installed by Italian masters of natural stone and glazed enamel. Most recently, a wall installation for Orlando International Airport “C Terminal”. Victor’s paintings are included in corporate and museum collections throughout the South, plus having numerous solo exhibitions. Victor’s career path includes 9 years Senior Art Director for Sea World and 20 years Senior Art Director Tupperware. Check out his website at Victorbokas.com.

Judges for the Winter Park Sidewalk Art Festival are selected annually for their in-depth knowledge and experience in multiple art media. Each year, they review digital images from all applicants and select the exhibiting artists in a process called jurying. This year's judges are: Chris Dahlquist, John W. Kincade and Brent Kee Young. The artists in this year’s Festival were originally selected by these three judges to exhibit during the 2020 show that was canceled. Since they were unable to exhibit, all of the artists were invited back for the 2021 Festival. The artwork displayed in the March WPSAF Virtual Festival will not be judged; however, in May, all three judges will return to Winter Park to judge the in-person Festival. During the in-person Festival, the panel of judges will review each exhibit to determine which artists will be considered for awards. After a booth is selected, the artist will select one of their pieces to submit to the judges for consideration. Award winners are determined by the judges on Saturday during the live event. Artists complete for 63 awards totaling $74,500. The Best of Show winner is purchased for $12,000 by The Winter Park Sidewalk Art Festival Board and donated to the City of Winter Park. Previous Best of Show winners are on permanent display at the Winter Park Public Library. A $5,000 “Art of Philanthropy” Purchase Award is sponsored by the Edyth Bush Charitable Foundation. A $2,500 “Distinguished Work of Art” Award is presented through The Charles Hosmer Morse Museum of American Art. There are 10 Awards of Excellence of $2,000 each, 20 Awards of Distinction of $1,000 each and 30 Awards of Merit of $500 each.

Our Patrons Program was created to provide support of the Winter Park Sidewalk Art Festival artists through dedicated funds pledged to purchase artwork during our annual show. By participating, Patrons make monetary pledges for given levels of spending. Up to 95 percent of your contribution stays with you to purchase art and the remainder goes to support The Winter Park Sidewalk Art Festival. This financial commitment to the purchase of art generates enthusiasm in the artist’s community and attracts the most outstanding artists who display on the outdoor circuit. We invite you to experience the unique and rewarding opportunity to become a patron of The Winter Park Sidewalk Art Festival. All Patrons are invited to attend special Patron events including meet-and-greets throughout the year. All patrons receive exclusive concert seating and refreshments in the Patrons tent throughout the Art Festival weekend. For more information, contact the Patrons Chair at patrons@wpsaf.org or leave a voice message at the Winter Park Sidewalk Art Festival voice mail system 407-644-7207.

By volunteering you will experience a one-of-a kind behind-the-scenes opportunity to gain a deeper appreciation for the artists and their award-winning artwork. The volunteers are the backbone of the festival. They help make the Winter Park Sidewalk Art Festival one of the top outdoor festivals in the country. We Have a Place for You: As a volunteer, you'll enjoy being involved in many activities throughout the 3-day festival. If you are willing to assist in the areas of the festival where you may be most needed, we have a place for you! Sign-up to be on the Merchandise Team to participate in the sales of festival T-shirts and posters. Join the Children's Workshop Team to encourages young artists with easel painting activities. As part of the Artists' Care Team, you will assist over 200 Artists with booth sitting and kind care activities. The More the Merrier! We would love to have you volunteer with your family and friends! High school, college, school clubs and organizations can earn valuable community service points participating in our volunteer opportunities. Community clubs and organizations are welcome to join our many volunteer roles for this popular community event. Volunteer Perks - Free Volunteer T-Shirt - Free WPSAF Poster - Meet the Artists - Have fun getting to know other volunteers! - Become part of the WPSAF Volunteer Team! To apply, visit: https://www.wpsaf.org/support/volunteer/index

The Winter Park Sidewalk Art Festival Foundation, Inc. (the “Foundation”) provides grants to promote community appreciation of the arts and supports art education through scholarships and programs. The Foundation supports The Children’s Workshop, The Leon Theodore Schools Exhibit, The Emerging Artists Program, The Image Review Workshop and Performing Arts at The Winter Park Sidewalk Art Festival. It also funds the Jean Alice Oliphant Scholarship at Rollins College in Winter Park and The Winter Park Sidewalk Art Festival Scholarship at the University of Central Florida in Orlando. Since 2008 the Foundation has had a continuing mission to enhance art appreciation, art education and community spirit. Each year during the festival more than a thousand children take the opportunity to express their creativity though easel painting and more than 500 children per day visit the museum workshops and participate in hands-on art projects. In 2019 more than 4,500 Orange County students have had the thrill of having their artwork showcased and judged at the Leon Theodore Schools Exhibit. The Foundation received funding in 2019 from donations by The Joe and Sarah Galloway Foundation, The Edyth Bush Charitable Foundation, The Rotary Club of Winter Park, The Pocket Program and The Winter Park Sidewalk Art Festival. The Internal Revenue Service approved the Foundation, a Florida corporation not-for-profit, as a 501(c) 3 tax-exempt entity in September of 2008.