Winter Park Sidewalk Art Festival: 7 Things to Know

Winter Park Sidewalk Art Festival is one of the largest and prestigious festivals to be celebrated in Florida. With its inception in March 1960, the festival continues to be a community project where artists and spectators worldwide come together to participate in the festival and observe.

The festival takes place in Central Park and along Park Avenue in Winter Park. This outdoor art festival aims to bring together art lovers and local artists, and an all-volunteer board produces it.

The Winter Park Sidewalk Art Festival

The Winter Park Sidewalk Art Festival, conducted annually, draws around 350,000 visitors per year from different regions. Over 1100 artists apply for the various categories in the festival, out of which 225 artists are selected. A panel of three esteemed judges makes the final selections. 

The Jury of the Winter Park Sidewalk Art Festival

The jurist panel is selected every year from around the country, considering their knowledge and understanding of all the different categories featured in the festival.

All applications’ digital images are reviewed in October to select the Festival Artists and the Waitlist Artists. The judging process could be tiresome as around 1100 artists are participating in the occasion. The jury should be able to go through each of them with utmost observation and clarity.

In March, the jury will examine the works of the artists they consider deserving of the awards. The artist is supposed to select one art piece from their artworks which are to be given an entry for participation in the festival. The artist’s one-piece for the competition is the most crucial because it determines his performance at the festival. 

The jury studied the artwork, and the decision will be made upon the quality of the piece produced before them. Previously award-winning artwork is not eligible for winning the award a second time. 

A list of artists participating in the festival will be published on the Winter Park Sidewalk Art Festival’s official website, along with their medium and the booth provided.  

Only one booth is provided for each participating artist except those accepted to participate in two categories. 

The Winter Park Sidewalk Art Festival foundation seeks to impart art education through various scholarship programs and provides grants for promoting and appreciating art among the community. They also fund the Winter Park Sidewalk Art Festival Scholarship at the University of Central Florida in Orlando and the Jean Alice Oliphant Scholarship at Rollins College in Winter Park.

The foundation also supports The Emerging Artists Program, The Leon Theodore Schools Exhibit, The Children’s Workshop, Performing Arts, and the Image Review Workshop at Park Avenue’s Winter Park Sidewalk Art Festival.

Winter Park Sidewalk Art Festival: 7 Things to Know

1. Fine Arts and Crafts

Winter Park Sidewalk Art Festival
Photo from Winter Park Sidewalk Art Festival website

The festival showcases various fine arts and crafts from multiple categories such as clay, drawings, pastels, fiberglass, digital art, photography, sculpture, graphics and printmaking, painting, leather, jewelry, metal, mixed media 3D, mixed media 2D, watercolor, and wood.

2. Emerging Artists

They have also included a special category called the Emerging Artists to induce new artists to participate on this occasion.

One of the festival’s major highlights is its special category, the Emerging Artists, where three new artists are selected to participate. This Emerging Artists program was started in 1977 and provided the new-to-art artists with exposure and made them aware of new and bigger art possibilities as a career. The same panel of judges selects these artists.

There is also a separate booth to feature the student art from Central Florida Schools and a separate interactive art space for the kids.

3. Orange County Public and Private Schools

Orange County public and private schools have always been a part of the festival. Children from these schools have showcased some fantastic and brilliant artworks developed by them. Participation of students from these schools started from the beginning of this art festival in 1960. 

4. Children’s Workshop

The Children’s Workshop set up in the Park lets the children create their artwork there and allows them to take it to their homes. 

Easel Painting is the major form of art that attracts these younger kids’ interests, where they get to paint picture easels outdoors. This particular activity helps the children in their growth as well as in enhancing their creative minds. Around 1000 children and families participate in the easel painting in a year. 

The community believes in the role of art in people’s minds, especially kids of a younger age, and how it helps them shape their world through the years. 

The Children’s Workshop Village is open on all days of the festival and is free but needs the presence of an adult to sign them up. The Workshop is situated west of the railroads and north of Morse Boulevard, near the Post Office. 

5. Winter Park Sidewalk Art Festival Awards

In the winter park sidewalk art festival, the artists compete for 63 awards, amounting to $74500. The awards are distributed for titles like The Best of Show, purchased by The Winter Park Sidewalk Art Festival Board for $12000, and donated to the City of Winter Park. 

The other awards presented to the winners include the Edyth Bush Charitable Foundation’s Art of Philanthropy Purchase Award and the Distinguished Work of Art Award gave through The Charles Hosmer Morse Museum of American Art. Besides these, there are 10 Awards of excellence of $2000 each, Awards of Distinction for 20 artists of $1000 each, and 30 Awards of Merit each of $500.

6. Entertainment Events

Apart from the three-day art festival, the community has also set up other entertaining events for the visitors. Musical concerts begin right from the first day onwards at the festival and continue for all three days. 

These free entertainment events are set up at the main stage in north Central Park. The performers in these concerts will be local artists.  

7. Buy Your Favorite Merchandise!

Visitors also get to buy their favorite merchandise of the Winter Park Sidewalk Art Festival. From their tents set up at various parks, you can purchase products like the Art Festival T-shirts, posters, and other valuable items. 

Three tents are set up at the fair, and they are at Park and New England Avenue at the south entrance, Morse Boulevard and Park Avenue at the north entrance and, Park and Garfield Avenue at the north entrance.

A separate tent will be set next to the festival headquarters at Park Avenue and Morse Boulevard to sell and buy vintage merchandise.

Although all these festivities related to the event seem to be conducted in a friendly way, it should be noted that some strict rules and regulations should be accepted and followed by everyone attending the fest. 

Reproduction of any original artwork is strictly prohibited. This includes copies from works of advertisements, commercial or widely circulated newspapers, offset prints, etc. 

Traditional artworks, including soap, candles, homemade foods, etc., should not be produced in this event and mass-produced notebooks and cards. Other prohibited things include alcohol or other drugs, pets, and generators. 

Anyone who refuses to abide by these rules and thereby disgrace the entire community will be subject to punishment by the authorities. 

This prestigious outdoor art festival has always been an inviting factor for the tourists visiting the state of Florida each year. Winter Park Sidewalk Art Festival is consistently positioned as one of the country’s many top juried fine arts festivals. The festival ranked “2019 Best Art Fairs” of the Art Fair Calendar and the Sunshine Magazine’s “Top 100” list

Those applying for the festival must have four booth shots of them. Each individual can submit up to 3 applications.

Food and accommodations are available near the park. One should find a big array of cafes and restaurants settled along the park. The festival does not provide housing, but you could find places to stay near the park. 

There is no allotted space for parking. You should find parking for your vehicles along park avenue. However, if you are coming to the fest with your bicycle, you could find a free bike corral on Morse Boulevard across the street from the Winter Parks Train parking station. 

The art festival is set to premiere its 62nd edition in the year 2021. The event will take place on March 19,20,21 at the same home, at Central Park, along the Park Avenue of downtown Florida. The timing is settled down from 9:00 am to 6:00 pm on Friday and Saturday. However, there is a slight change in the schedule on Sunday, from 9:00 am to 5:00 pm.

So if you plan for a quick outing with family or friends, the Winter Park Sidewalk Art Festival could be your best choice. With equal entertainment possibilities for both the young and old alike, there is no doubt about having fun in this beautiful outdoor festival. 

Last Updated on by Sanjana


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