Wednesday, July 30, 2014
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About the Festival

History of the Show-old


The Winter Park Sidewalk Art Festival is one of the nation’s oldest, largest and most prestigious juried outdoor art festivals, consistently rated among the top shows by Sunshine Artist and American Style magazines. Each year more than 350,000 visitors enjoy the show. This year about 1,200 artists from around the world applied for entry and an independent panel of judges selected 225 national and international artists to attend the show. The National Endowment for the Arts, The White House, Congress and many others have lauded the Festival for promoting art and art education in Central Florida. An all volunteer board of directors runs the annual Festival, now celebrating its 54th year.

The Winter Park Sidewalk Art Festival was started by a handful of enthusiasts as a community project to benefit local artists and art lovers. The first festival was held on Park Avenue in March 1960. The festival featured original works of art and, after being advertised for just three weeks before the opening, drew 90 exhibiting artists. Over the next decade, the festival grew to over 600 artists and was spread out over Park Avenue from Fairbanks Avenue to Canton Avenue and on all cross streets. For the past 30 years or so, the festival has been contained solely in the park area and currently features 225 artists and 3 emerging artists. A loving art community has created and nurtured a successful festival that looks forward to another 50 years in Central Park.


There is a wide variety of outstanding artwork. Categories include: Clay, Digital Art, Drawing and Graphics, Fiber, Glass, Jewelry, Leather, Metal, Mixed Media, Painting, Photography, Sculpture and Wood.


The artists compete for 63 awards totaling $72,500. Best of Show is $10,000. The Winter Park Sidewalk Art Festival Committee purchases the Best of Show art and donates it to the City of Winter Park. (All previous Best of Show winners are on permanent display at the Winter Park Public Library.) There are also 10 Awards of Excellence; each is $2,000.  There are 20 Awards of Distinction; each is $1,000 and there are 30 Awards of Merit; each is $500. In addition, a $2,500 Award for a Distinguished Work of Art is presented through the Charles Hosmer Morse Museum of American Art. A $5,000 "Art of Philanthropy" purchase award donated by the Edyth Bush Charitable Foundation has been added for 2013.


2014 Award Winners

Best of Show

"Open Sea"
Matthew Cornell
Orlando, FL
Booth 1

Read more: 2014 Award Winners


Children's Workshop Village


Children’s Workshop Village

Hey, Kids! Come Create! Have Fun! It’s Free!

Boys and girls, here is your chance to show everyone your artistic abilities by creating unique artwork. Best of all, it’s all free and kids can keep what they make!

The fun happens between 10 AM and 4 PM at the Children’s Workshop Village on Friday, Saturday and Sunday. The Children’s Workshop Village is appropriate for children of all ages.  

One of the most popular activities at the Village is easel painting on Saturday and Sunday, 10:00 AM – 3:00 PM. In addition, each of our museum partners has prepared interesting hands-on arts and crafts activities on Friday, Saturday and Sunday, 10:00 AM – 4:00 PM.

Read more: Children's Workshop Village


2014 Judges

Each year the art festival selects three judges from around the country; they each have artistic credentials in varying fields. In October, these judges select the artists that will participate in the show from the more than 1,000 artists who apply. The images that they view for selection have numbers and no names so the judges won’t be swayed by recognition of the artist. These same judges attend the festival in March and view each artist’s whole body of work in order to select the winners of this year’s awards.

Read more: 2014 Judges

Winter Park Sidewalk Art Festival
P.O. Box 597
Winter Park, FL 32790-0597