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Event Overview:
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 applied for this year’s Festival. An independent panel of three judges selected the 225 artists exhibiting their works. The Festival consistently ranks as one of the top juried fine-art festivals in the country. Recent accolades include the #4 ranking in Art Fair Calendar’s “2016 Best Art Fairs” and Art Fair Source Book’s listing in their “Top 10 Fine Art Shows, 2016”. The Festival is also listed in Sunshine Artist Magazine’s “Top 100”.
CATEGORIES
The Festival features a wide variety of fine arts and crafts in the following categories: clay, digital art, drawings & pastels, fiber, glass, graphics & printmaking, jewelry, leather, metal, mixed media 2D, mixed media 3D, painting, photography, sculpture, watercolor and wood as well as our Emerging Artists.
AWARDS
Artists complete for 63 awards totaling $72,500. The Best of Show winner is purchased for $10,000 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.
FAMILY FUN
Girls and boys can create their own artwork at the Children’s Workshop Village. Easel painting is very popular, and local art centers and museums feature a variety of fun, hands-on art activities for children. Admission is free and participants may take home their artistic creations. The Children’s Workshop Village hours are 10 a.m. – 4 p.m. on Friday, Saturday and Sunday. Easel painting is from 10 a.m. – 3 p.m. on Saturday and Sunday.
LEON THEODORE SCHOOLS EXHIBIT
The place to discover the talented artists of the next generation is at the Leon Theodore Schools Exhibit where artwork by thousands of Orange County students is on display. The creativity and level of expertise displayed by these young artists will delight and amaze you. Be sure to check out this wonderful exhibit.
COMPLIMENTARY BIKE VALET
Enjoy the Festival while your bike is safely monitored. Located on Morse Boulevard across the street from the Amtrak Station parking lot, a free bike valet service is provided during Festival hours by the Winter Park Pedestrian and Bicycle Advisory Board.
Exhibitor Information:
The Winter Park Sidewalk Art Festival is one of the nation's oldest and most prestigious juried fine art shows. It consistently ranks among the most highly regarded outdoor art shows in the nation. Cash awards total $72,500 and dedicated Patron purchase funds, over $70,000. The Festival features original artwork representing the current work of the exhibiting artists.
The show is located in historic downtown Winter Park, Florida, a beautifully landscaped area where artists' booths nestle under large oak trees throughout Central Park and stretch along Park Avenue. The three-day event takes place on March 16, 17, and 18, 2018 in the heart of this charming city which is known for its brick streets, unique boutique shops, and inviting outdoor cafes and bistros. Attendance at the Festival is expected to reach over 350,000 people who will view the artwork of up to 225 artists and 3 emerging artists. One of Central Florida's largest annual outdoor events, the Festival also features a wide variety of entertainment on the stage in Central Park, food and beverage to please the whole family, a popular exhibit of student art from Central Florida schools, and many interactive art activities for the kids.
Portions of the Festival's proceeds are donated to the Winter Park Sidewalk Art Festival Foundation to fund scholarships through the Jean Alice Oliphant Scholarship at Rollins College and The Winter Park Sidewalk Art Festival Scholarship at the University of Central Florida.
Source : Event Website
Event Name | City | State | Atendance | Exhibitors | Date |
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Winter Park Sidewalk Art Festival 2023 | Winter Park | Florida | ![]() estimated |
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Mar 17, 2023 |
Winter Park Sidewalk Art Festival 2021 | - | - | Mar 15, 2021 | ||
Winter Park Sidewalk Art Festival 2020 | - | - | Mar 20, 2020 | ||
Winter Park Sidewalk Art Festival 2018 | ![]() estimated |
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Mar 16, 2018 | ||
Winter Park Sidewalk Art Festival 2017 | - | - | Mar 17, 2017 | ||
Winter Park Sidewalk Art Festival 2016 | Winter Park | Florida | - | - | Mar 18, 2016 |
Event Name | City | State | Atendance | Exhibitors | Date |
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Waterfowl Festival 2025 | Easton | Maryland | ![]() estimated |
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Nov 14, 2025 |