CATEGORIES

The festival features a wide variety of fine arts and crafts in the following categories: clay, digital art, drawings and pastels, fiber, glass, graphics and printmaking, jewelry, leather, metal, mixed media-2D, mixed media-3D, painting, photography, sculpture, watercolor and wood as well as an Emerging Artists category.

AWARDS

Artists compete for 64 awards totaling $76,500. The Best of Show purchase award was increased in 2019 to $12,000. The festival donates the winning work to the City of Winter Park, and all 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, while a $2,500 “Distinguished Work of Art” Award is presented through the Charles Hosmer Morse Museum of American Art. New in 2023 is a $2,000 annual “Monte Livermore Celebration of Nature Award”. 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.

MUSIC AND ENTERTAINMENT

In 2025, the Friday Night Concert returns.  Stay tuned for details about the 2025 entertainment lineup!

CONCESSIONS

A wide variety of food options are available at the festival each year, including food tents and kiosks in the park, as well as local Winter Park restaurants and cafes.

The festival does not hire individual concession vendors to participate in the festival.  The festival contracts with a concessions company and they coordinate with the individual vendors that participate.  

MERCHANDISE

Winter Park Sidewalk Art Festival T-shirts and other memorabilia are available at three merchandise sales tents. The tents are located at the south entrance (Park and New England avenues), at the center intersection (Morse Boulevard and Park Avenue), and at the north entrance (Park and Garfield avenues). Posters will be sold at the three merchandise tents, while a vintage poster & merchandise tent will be located across the mulch path next to the festival headquarters at Park Avenue and Morse Boulevard.

CHILDREN'S WORKSHOP

Girls and boys can create their own artwork at the Children’s Workshop.  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 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 CORRAL

Ride your bike to the festival and park it at the free Bike Corral provided by the Winter Park Pedestrian and Bicycle Advisory Board. The corral is located off Morse Boulevard across the street from the Train Station parking lot.

Visitors are asked to be aware of any new CDC guidelines for keeping safe in crowded areas. For your safety, hand washing stations and sanitizer will be available throughout the park.

No animals are allowed (except certified service animals) in Central Park or on Park Avenue between New England and Canton Avenues during festival hours, per a City of Winter Park Ordinance.

For more information, call 407-644-7207.

To view the 2025 Festival Map, click below.